Abstract:
The present invention relates to a pyrazolochalcone of formula A useful as potential antitumor agent against human cancer cell lines and a process for the preparation thereof. Formula A wherein, R1, R2, R3, R4, R5=H, Cl, F, CH 3 , OCH 3 , 3,4(OCH 2 O) X=H, Cl, CH 3 , OCH 3 , 3,4(OCH 2 O), NH 2 , NO 2 , OH, dotted line indicates optionally cyclic structure.

Description:
FIELD OF THE INVENTION 
       [0001]    The present invention relates to pyrazolochalcones as potential anticancer agents. The present invention also relates to the synthesis and biological evaluation of novel pyrazolochalcones of formula A as potential anticancer agents. 
       BACKGROUND OF THE INVENTION 
       [0002]    Tubulin is an essential eukaryotic protein that plays critical roles in cell division and is an established target of anticancer drug development. Combretastatins (S 1 ), chalcones (S 2 ), podophyllotoxins (S 3 ) and Colchicines (S 4 ) are the notable examples of compounds that inhibit microtubule assembly by binding to tubulin. Many mechanisms of action have been identified, including the inhibition of tubulin assembly, inhibition of angiogenesis, induction of apoptosis, anti-estrogenic activity and reversal of multidrug resistance or a combination of these mechanisms (Ducki, S. The development of chalcones as promising anticancer agents. Invest. New Drugs. 2007, 10, 42-46; Boumendjel, A., Boccard, J., Carrupt, P.-A., Nicolle, E., Blanc, M., Geze, A., Choisnard, L., Wouessidjewe, D., Matera, E.-L. and Dumontet, C. Antimitotic and Antiproliferative activities of chalcones.  J. Med. Chem.  2008, 51, 2307-2310; Sharma, N., Mohanakrishnan, D., Shard, A., Sharma, A., Saima, Sinha, A. K. and Sahal, D. Stilbene-chalcone hybrids: design, synthesis, and evaluation as a new class of antimalarial scaffolds that trigger cell death through stage specific apoptosis.  J. Med. Chem.  2012, 55, 297-311). A more recent reevaluation of this type of compounds by NCI against human tumor cell lines reconfirmed that, like colchicine, they are effective inhibitors of tubulin polymerization. Pyrazole (NSC-45410) is a low molecular weight, heterocyclic compound which has been considered for reevaluation in the clinic as a potential cytotoxic agent. (O&#39;Dwyer. P J, King S A, Plowman J, Grieshaber C K, Hoth D F, Leyland-Jones B. Pyrazole: preclinical reassessment. Invest New Drugs; 1988, 6, 305-310; Sidique, S., Ardecky, R., Su, Y., Narisawa, S., Brown, B., Millan, J. L., Sergienko, E. and Cosford, N. D., Design and synthesis of pyrazole as potent and selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP). Bioorg. Med. Chem. Lett. 2009, 19, 222-225). Biochemical mechanistic studies performed with dihydropyridopyrazole (S 3 ) compounds showed that these molecules inhibit in vitro tubulin polymerization and disrupt the formation of mitotic spindles in dividing cells at low nanomolar concentrations, in a manner similar to podophyllotoxin itself (Magedov, I. V., Frolova, L., Manpadi, M., Bhoga, U. D., Tang, H., Evdokimov, N. M., George, O., Georgiou, K. H., Renner, S., Getlik, M., Kinnibrugh, T. L., Fernandes, M. A., van Slambrouck, S., Steelant, W. F. A., Shuster, C. B., Rogelj, S., van Otterlo, W. A. L. and Kornienko, A. Anticancer properties of an important drug lead podophyllotoxin can be efficiently mimicked by diverse heterocyclic scaffolds accessible via one-step synthesis.  J. Med. Chem.  2011, 54, 4234-4246). The microtubules possesses three sites for ligand binding—the vinca domain, colchicine domain and taxol domain. However, occurrence of peripheral neuropathy, high systemic toxicity and drug resistance are major limitations in the development of antimicrotubule agents as drugs (F. Pellegrini, D. R. Budman, Tubulin function, action of antitubulin drugs, and new drug development.  Cancer. Invest.  2005, 23, 264-273). The unique feature of microtubule-binding agents, in contrast to other categories of anticancer drugs, is their incredible structural complexity and diversity, which provides many possibilities for new scaffold design. In recent years, combination chemotherapy with agents possessing different mechanisms of action is one of the methods, that is being adopted to treat cancer. Therefore, hybrid compounds like pyrazolochalcones described in the present invention that contain pyrazole as well as chalcone pharmacophores with different mode of action could be beneficial for the treatment of cancer. 
         [0000]    
       
                 
         
             
             
         
       
     
       OBJECTIVES OF THE INVENTION 
       [0003]    The main objective of the present invention is to provide pyrazolochalcones useful as antitumor agents. 
         [0004]    Yet another object of this invention is to provide a process for the preparation of pyrazolochalcones. 
         [0005]    Further object of the present invention is to provide novel pyrazolochalcones of formula A1 and A2 as potential anticancer agents. 
       SUMMARY OF THE INVENTION 
       [0006]    Accordingly the present invention provides a pyrazolochalcone of formula A, 
         [0000]    
       
                 
         
             
             
         
       
     
         [0000]    wherein,
 
R1, R2, R3, R4, R5=H, Cl, F, CH 3 , OCH 3 , 3,4(OCH 2 O)
 
X=H, Cl, F, CH 3 , OCH 3 , 3,4(OCH 2 O), NH 2 , NO 2 , OH.
 
         [0007]    In an embodiment of the invention the pyrazolochalcone of formula A is selected from the group consisting of pyrazolochalcone of formula A1 and pyrazolochalcone of formula A2 
         [0000]    
       
                 
         
             
             
         
       
     
         [0000]    wherein,
 
R1, R2, R3, R4, R5=H, Cl, F, CH 3 , OCH 3 , 3,4(OCH 2 O)
 
X 1 =H, Cl, F, CH 3 , OCH 3 , 3,4(OCH 2 O), NH 2 , NO 2 , OH.
 
         [0000]    
       
                 
         
             
             
         
       
     
         [0000]    wherein,
 
R1, R2, R3, R4, R5=H, Cl, F, CH 3 , OCH 3 , 3,4(OCH 2 O)
 
X 2 =H, OCH 3  
 
         [0008]    In another embodiment of the present invention the pyrazolochalcone of formula A1 is selected from the group consisting of compounds of formulae 6a-21a, 6b-21b, 6c-21c, 6d-21d, 6e-21e, 6f-21f, 6g-21g, 6h-21h, 6i-21i, 6j-21j, 6k-21k and 6l-21l and pyrazolochalcone of formula A2 is selected from the group consisting of compounds of formulae 22a-24a, 22b-24b, 22c-24c, 22d-24d, 22e-24e, 22f-24f, 22g-24g, 22h-24h, 22i-24i, 22j-24j, 22k-24k and 22l-24l. 
         [0000]    
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
         
           
             wherein X 1 =H, Cl, F, CH 3 , OCH 3 , 3,4(OCH 2 O), NH 2 , NO 2 , OH 
           
         
       
     
         [0000]    
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
     
         [0010]    In yet another embodiment of the invention the pyrazolochalcone of formula A is selected from the group consisting of:
   (E)-1-phenyl-3-(3-phenyl-1H-pyrazol-5-yl) prop-2-en-1-one (6a);   (E)-3-(3-(4-methoxyphenyl)-1H-pyrazol-5-yl)-1-phenylprop-2-en-1-one (6b);   (E)-3-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-5-yl)-1-phenylprop-2-en-1-one (6c);   (E)-3-(3-(3,5-dimethoxyphenyl)-1H-pyrazol-5-yl)-1-phenylprop-2-en-1-one (6d); (E)-1-phenyl-3-(3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (6e); (E)-3-(3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)-1-phenylprop-2-en-1-one (6f); (E)-3-(3-(3,4-dichlorophenyl)-1H-pyrazol-5-yl)-1-phenylprop-2-en-1-one (6g); (E)-3-(3-(3,4-difluorophenyl)-1H-pyrazol-5-yl)-1-phenylprop-2-en-1-one (6h);   (E)-3-(3-(4-fluorophenyl)-1H-pyrazol-5-yl)-1-phenylprop-2-en-1-one (6i);   (E)-3-(3-(4-chlorophenyl)-1H-pyrazol-5-yl)-1-phenylprop-2-en-1-one (6j);   (E)-3-(3-(2-fluoro-4-methoxyphenyl)-1H-pyrazol-5-yl)-1-phenylprop-2-en-1-one (6k);   (E)-3-(3-(3,4-dimethylphenyl)-1H-pyrazol-5-yl)-1-phenylprop-2-en-1-one (6l);   (E)-1-(4-methoxyphenyl)-3-(3-phenyl-1H-pyrazol-5-yl)prop-2-en-1-one (7a);   (E)-1-(4-methoxyphenyl)-3-(3-(4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (7b);   (E)-3-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-5-yl)-1-(4-methoxyphenyl)prop-2-en-1-one (7c);   (E)-3-(3-(3,5-dimethoxyphenyl)-1H-pyrazol-5-yl)-1-(4-methoxyphenyl)prop-2-en-1-one (7d);   (E)-1-(4-methoxyphenyl)-3-(3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (7e);   (E)-3-(3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)-1-(4-methoxyphenyl)prop-2-en-1-one (7f);   (E)-3-(3-(3,4-dichlorophenyl)-1H-pyrazol-5-yl)-1-(4-methoxyphenyl)prop-2-en-1-one (7g);   (E)-3-(3-(3,4-difluorophenyl)-1H-pyrazol-5-yl)-1-(4-methoxyphenyl)prop-2-en-1-one (7h);   (E)-3-(3-(4-fluorophenyl)-1H-pyrazol-5-yl)-1-(4-methoxyphenyl)prop-2-en-1-one (7i);   (E)-3-(3-(4-chlorophenyl)-1H-pyrazol-5-yl)-1-(4-methoxyphenyl)prop-2-en-1-one (7i);   (E)-3-(3-(2-fluoro-4-methoxyphenyl)-1H-pyrazol-5-yl)-1-(4-methoxyphenyl)prop-2-en-1-one (7k);   (E)-3-(3-(3,4-dimethylphenyl)-1H-pyrazol-5-yl)-1-(4-methoxyphenyl)prop-2-en-1-one (7l);   (E)-1-(3,4-dimethoxyphenyl)-3-(3-phenyl-1H-pyrazol-5-yl)prop-2-en-1-one (8a);   (E)-1-(3,4-dimethoxyphenyl)-3-(3-(4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (8b);   (E)-1-(3,4-dimethoxyphenyl)-3-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (8c);   (E)-1-(3,4-dimethoxyphenyl)-3-(3-(3,5-dimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (8d);   (E)-1-(3,4-dimethoxyphenyl)-3-(3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (8e);   (E)-3-(3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one (8f);   (E)-3-(3-(3,4-dichlorophenyl)-1H-pyrazol-5-yl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one (8g);   (E)-3-(3-(3,4-difluorophenyl)-1H-pyrazol-5-yl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one (8h);   (E)-1-(3,4-dimethoxyphenyl)-3-(3-(4-fluorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (8i);   (E)-3-(3-(4-chlorophenyl)-1H-pyrazol-5-yl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one (8j);   (E)-1-(3,4-dimethoxyphenyl)-3-(3-(2-fluoro-4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (8k);   (E)-1-(3,4-dimethoxyphenyl)-3-(3-(3,4-dimethylphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (8l);   (E)-1-(3,5-dimethoxyphenyl)-3-(3-phenyl-1H-pyrazol-5-yl)prop-2-en-1-one (9a);   (E)-1-(3,5-dimethoxyphenyl)-3-(3-(4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (9b);   (E)-1-(3,5-dimethoxyphenyl)-3-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (9c);   (E)-1-(3,5-dimethoxyphenyl)-3-(3-(3,5-dimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (9d);   (H)-1-(3,5-dimethoxyphenyl)-3-(3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (9e);   (E)-3-(3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)-1-(3,5-dimethoxyphenyl)prop-2-en-1-one (9f);   (E)-3-(3-(3,4-dichlorophenyl)-1H-pyrazol-5-yl)-1-(3,5-dimethoxyphenyl)prop-2-en-1-one (9g);   (E)-3-(3-(3,4-difluorophenyl)-1H-pyrazol-5-yl)-1-(3,5-dimethoxyphenyl)prop-2-en-1-one (9h);   (E)-1-(3,5-dimethoxyphenyl)-3-(3-(4-fluorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (9i);   (E)-3-(3-(4-chlorophenyl)-1H-pyrazol-5-yl)-1-(3,5-dimethoxyphenyl)prop-2-en-1-one (9j);   (E)-1-(3,5-dimethoxyphenyl)-3-(3-(2-fluoro-4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (9k);   (E)-1-(3,5-dimethoxyphenyl)-3-(3-(3,4-dimethylphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (9l);   (E)-3-(3-phenyl-1 FI-pyrazol-5-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (10a);   (E)-3-(3-(4-methoxyphenyl)-1H-pyrazol-5-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (10b);   (E)-3-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-5-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (10c);   (E)-3-(3-(3,5-dimethoxyphenyl)-1H-pyrazol-5-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (10d);   (E)-1-(3,4,5-trimethoxyphenyl)-3-(3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (10e);   (E)-3-(3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (10f);   (E)-3-(3-(3,4-dichlorophenyl)-1H-pyrazol-5-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (10g);   (E)-3-(3-(3,4-difluorophenyl)-1H-pyrazol-5-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (10h);   (E)-3-(3-(4-fluorophenyl)-1H-pyrazol-5-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (10i);   (E)-3-(3-(4-chlorophenyl)-1H-pyrazol-5-yl)-1-(3,4, 5-trimethoxyphenyl)prop-2-en-1-one (10j);   (E)-3-(3-(2-fluoro-4-methoxyphenyl)-1H-pyrazol-5-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (10k);   (E)-3-(3-(3,4-dimethylphenyl)-1H-pyrazol-5-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (10l);   (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(3-phenyl-1H-pyrazol-5-yl)prop-2-en-1-one (11a);   (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(3-(4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (11b);   (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (11c);   (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(3-(3,5-dimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (11d);   (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(3-(3,4, 5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (11e);   (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)prop-2-en-1-one (11f);   (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(3-(3,4-dichlorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (11g);   (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(3-(3,4-difluorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (11h);   (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(3-(4-fluorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (11i);   (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(3-(4-chlorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (11j);   (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(3-(2-fluoro-4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (11k);   (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(3-(3,4-dimethylphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (11l);   (E)-1-(3,4-dichlorophenyl)-3-(3-phenyl-1H-pyrazol-5-yl)prop-2-en-1-one (12a);   (E)-1-(3,4-dichlorophenyl)-3-(3-(4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (12b);   (E)-1-(3,4-dichlorophenyl)-3-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (12c);   (E)-1-(3,4-dichlorophenyl)-3-(3-(3,5-dimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (12d);   (E)-1-(3,4-dichlorophenyl)-3-(3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (12e);   (E)-3-(3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)-1-(3,4-dichlorophenyl)prop-2-en-1-one (12f);   (E)-1-(3,4-dichlorophenyl)-3-(3-(3,4-dichlorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (12g);   (E)-1-(3,4-dichlorophenyl)-3-(3-(3,4-difluorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (12h);   (E)-1-(3,4-dichlorophenyl)-3-(3-(4-fluorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (12i);   (E)-3-(3-(4-chlorophenyl)-1H-pyrazol-5-yl)-1-(3,4-dichlorophenyl)prop-2-en-1-one (12j);   (E)-1-(3,4-dichlorophenyl)-3-(3-(2-fluoro-4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (12k);   (E)-1-(3,4-dichlorophenyl)-3-(3-(3,4-dimethylphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (12l);   (E)-1-(3,4-difluorophenyl)-3-(3-phenyl-1H-pyrazol-5-yl)prop-2-en-1-one (13a);   (E)-1-(3,4-difluorophenyl)-3-(3-(4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (13b);   (E)-1-(3,4-difluorophenyl)-3-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (13c);   P-1-(3,4-difluorophenyl)-3-(3-(3,5-dimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (13d);   (E)-1-(3,4-difluorophenyl)-3-(3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (13e);   (E)-3-(3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)-1-(3,4-difluorophenyl)prop-2-en-1-one (13f);   (E)-3-(3-(3,4-dichlorophenyl)-1H-pyrazol-5-yl)-1-(3,4-difluorophenyl)prop-2-en-1-one (13g);   (E)-1-(3,4-difluorophenyl)-3-(3-(3,4-difluorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (13h);   (E)-1-(3,4-difluorophenyl)-3-(3-(4-fluorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (13i);   (E)-3-(3-(4-chlorophenyl)-1H-pyrazol-5-yl)-1-(3,4-difluorophenyl)prop-2-en-1-one (13j);   (E)-1-(3,4-difluorophenyl)-3-(3-(2-fluoro-4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (13k);   (E)-1-(3,4-difluorophenyl)-3-(3-(3,4-dimethylphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (13l);   (E)-1-(4-fluorophenyl)-3-(3-phenyl-1H-pyrazol-5-yl)prop-2-en-1-one (14a);   (E)-1-(4-fluorophenyl)-3-(3-(4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (14b);   (E)-3-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-5-yl)-1-(4-fluorophenyl)prop-2-en-1-one (14c);   (E)-3-(3-(3,5-dimethoxyphenyl)-1H-pyrazol-5-yl)-1-(4-fluorophenyl)prop-2-en-1-one (14d);   (E)-1-(4-fluorophenyl)-3-(3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (14e);   (E)-3-(3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)-1-(4-fluorophenyl)prop-2-en-1-one (14f);   (E)-3-(3-(3,4-dichlorophenyl)-1H-pyrazol-5-yl)-1-(4-fluorophenyl)prop-2-en-1-one (14g);   (E)-3-(3-(3,4-difluorophenyl)-1H-pyrazol-5-yl)-1-(4-fluorophenyl)prop-2-en-1-one (14h);   (E)-1-(4-fluorophenyl)-3-(3-(4-fluorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (14i);   (E)-3-(3-(4-chlorophenyl)-1H-pyrazol-5-yl)-1-(4-fluorophenyl)prop-2-en-1-one (14j);   (E)-3-(3-(2-fluoro-4-methoxyphenyl)-1H-pyrazol-5-yl)-1-(4-fluorophenyl)prop-2-en-1-one (14k);   (E)-3-(3-(3,4-dimethylphenyl)-1H-pyrazol-5-yl)-1-(4-fluorophenyl)prop-2-en-1-one   (14l);   (E)-1-(4-chlorophenyl)-3-(3-phenyl-1H-pyrazol-5-yl)prop-2-en-1-one (15a);   (E)-1-(4-chlorophenyl)-3-(3-(4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (15b);   (E)-1-(4-chlorophenyl)-3-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (15c);   (E)-1-(4-chlorophenyl)-3-(3-(3,5-dimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (15d);   (E)-1-(4-chlorophenyl)-3-(3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (15e);   (E)-3-(3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)-1-(4-chlorophenyl)prop-2-en-1-one (150;   (E)-1-(4-chlorophenyl)-3-(3-(3,4-dichlorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (15g);   (E)-1-(4-chlorophenyl)-3-(3-(3,4-difluorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (15h);   (E)-1-(4-chlorophenyl)-3-(3-(4-fluorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (15i);   (E)-1-(4-chlorophenyl)-3-(3-(4-chlorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (15j);   (E)-1-(4-chlorophenyl)-3-(3-(2-fluoro-4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (15k);   (E)-1-(4-chlorophenyl)-3-(3-(3,4-dimethylphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one   (15l);   (E)-1-(2-fluoro-4-methoxyphenyl)-3-(3-phenyl-1H-pyrazol-5-yl)prop-2-en-1-one (16a);   (E)-1-(2-fluoro-4-methoxyphenyl)-3-(3-(4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (16b);   (E)-3-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-5-yl)-1-(2-fluoro-4-methoxyphenyl)prop-2-en-1-one (16c);   (E)-3-(3-(3,5-dimethoxyphenyl)-1H-pyrazol-5-yl)-1-(2-fluoro-4-methoxyphenyl)prop-2-en-1-one (16d);   (E)-1-(2-fluoro-4-methoxyphenyl)-3-(3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (16e);   (E)-3-(3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)-1-(2-fluoro-4-methoxyphenyl)prop-2-en-1-one (16f);   (E)-3-(3-(3,4-dichlorophenyl)-1H-pyrazol-5-yl)-1-(2-fluoro-4-methoxyphenyl)prop-2-en-1-one (16g);   (E)-3-(3-(3,4-difluorophenyl)-1H-pyrazol-5-yl)-1-(2-fluoro-4-methoxyphenyl)prop-2-en-1-one (16h);   (E)-1-(2-fluoro-4-methoxyphenyl)-3-(3-(4-fluorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (16i);   (E)-3-(3-(4-chlorophenyl)-1H-pyrazol-5-yl)-1-(2-fluoro-4-methoxyphenyl)prop-2-en-1-one (16j);   1-(2-fluoro-4-methoxyphenyl)-3-(3-(2-fluoro-4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (16k);   (E)-3-(3-(3,4-dimethylphenyl)-1H-pyrazol-5-yl)-1-(2-fluoro-4-methoxyphenyl)prop-2-en-1-one (16l);   (E)-1-(3,4-dimethylphenyl)-3-(3-phenyl-1H-pyrazol-5-yl)prop-2-en-1-one (17a);   (E)-1-(3,4-dimethylphenyl)-3-(3-(4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (17b);   (E)-3-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-5-yl)-1-(3,4-dimethylphenyl)prop-2-en-1-one (17c);   (E)-3-(3-(3,5-dimethoxyphenyl)-1H-pyrazol-5-yl)-1-(3,4-dimethylphenyl)prop-2-en-1-one (17d);   (E)-1-(3,4-dimethylphenyl)-3-(3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (17e);   (E)-3-(3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)-1-(3,4-dimethylphenyl)prop-2-en-1-one (17f);   (E)-3-(3-(3,4-difluorophenyl)-1H-pyrazol-5-yl)-1-(3,4-dimethylphenyl)prop-2-en-1-one (17g);   (E)-3-(3-(3,4-dichlorophenyl)-1H-pyrazol-5-yl)-1-(3,4-dimethylphenyl)prop-2-en-1-one (17h);   (E)-1-(3,4-dimethylphenyl)-3-(3-(4-fluorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (17i);   (E)-3-(3-(4-chlorophenyl)-1H-pyrazol-5-yl)-1-(3,4-dimethylphenyl)prop-2-en-1-one (17j);   1-(3,4-dimethylphenyl)-3-(3-(2-fluoro-4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (17k);   (E)-1-(3,4-dimethylphenyl)-3-(3-(3,4-dimethylphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (17l);   (E)-1-(3-hydroxy-4-methoxyphenyl)-3-(3-phenyl-1H-pyrazol-5-yl)prop-2-en-1-one (18a);   (E)-1-(3-hydroxy-4-methoxyphenyl)-3-(3-(4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (18b);   (E)-3-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-5-yl)-1-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one (18c);   (E)-3-(3-(3,5-dimethoxyphenyl)-1H-pyrazol-5-yl)-1-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one (18d);   (E)-1-(3-hydroxy-4-methoxyphenyl)-3-(3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (18e);   (E)-3-(3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)-1-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one (18f);   (E)-3-(3-(3,4-dichlorophenyl)-1H-pyrazol-5-yl)-1-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one (18g);   (E)-3-(3-(3,4-difluorophenyl)-1H-pyrazol-5-yl)-1-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one (18h);   (E)-3-(3-(4-fluorophenyl)-1H-pyrazol-5-yl)-1-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one (18i);   (E)-3-(3-(4-chlorophenyl)-1H-pyrazol-5-yl)-1-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one (18j);   (E)-3-(3-(2-fluoro-4-methoxyphenyl)-1H-pyrazol-5-yl)-1-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one (18k);   (E)-3-(3-(3,4-dimethylphenyl)-1H-pyrazol-5-yl)-1-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one (18l);   (E)-1-(4-aminophenyl)-3-(3-phenyl-1H-pyrazol-5-yl)prop-2-en-1-one (19a);   (E)-1-(4-aminophenyl)-3-(3-(4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (19b);   (E)-1-(4-aminophenyl)-3-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (19c);   (E)-1-(4-aminophenyl)-3-(3-(3,5-dimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (19d);   (E)-1-(4-aminophenyl)-3-(3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (19e);   (E)-1-(4-aminophenyl)-3-(3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)prop-2-en-1-one (19f);   (E)-1-(4-aminophenyl)-3-(3-(3,4-dichlorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (19g);   (E)-1-(4-aminophenyl)-3-(3-(3,4-difluorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (19h);   (E)-1-(4-aminophenyl)-3-(3-(4-fluorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (19i);   (E)-1-(4-aminophenyl)-3-(3-(4-chlorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (19j);   (E)-1-(4-aminophenyl)-3-(3-(2-fluoro-4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (19k);   (E)-1-(4-aminophenyl)-3-(3-(3,4-dimethylphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (19l);   (E)-3-(3-phenyl-1H-pyrazol-5-yl)-1-p-tolylprop-2-en-1-one (20a);   (E)-3-(3-(4-methoxyphenyl)-1H-pyrazol-5-yl)-1-p-tolylprop-2-en-1-one (20b);   (E)-3-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-5-yl)-1-p-tolylprop-2-en-1-one (20c);   (E)-3-(3-(3,5-dimethoxyphenyl)-1H-pyrazol-5-yl)-1-p-tolylprop-2-en-1-one (20d);   (E)-1-p-tolyl-3-(3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (20e);   (E)-3-(3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)-1-p-tolylprop-2-en-1-one (20f);   (E)-3-(3-(3,4-dichlorophenyl)-1H-pyrazol-5-yl)-1-p-tolylprop-2-en-1-one (20g);   (E)-3-(3-(3,4-difluorophenyl)-1H-pyrazol-5-yl)-1-p-tolylprop-2-en-1-one (20h);   (E)-3-(3-(4-fluorophenyl)-1H-pyrazol-5-yl)-1-p-tolylprop-2-en-1-one (20i);   (E)-3-(3-(4-chlorophenyl)-1H-pyrazol-5-yl)-1-p-tolylprop-2-en-1-one (20j);   (E)-3-(3-(2-fluoro-4-methoxyphenyl)-1H-pyrazol-5-yl)-1-p-tolylprop-2-en-1-one (20k);   (E)-3-(3-(3,4-dimethylphenyl)-1H-pyrazol-5-yl)-1-p-tolylprop-2-en-1-one (20l);   (E)-1-(3-chloro-4-nitrophenyl)-3-(3-phenyl-1H-pyrazol-5-yl)prop-2-en-1-one (21a);   (E)-1-(3-chloro-4-nitrophenyl)-3-(3-(4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (21b);   (E)-1-(3-chloro-4-nitrophenyl)-3-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (21c);   (E)-1-(3-chloro-4-nitrophenyl)-3-(3-(3,5-dimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (21d);   (E)-1-(3-chloro-4-nitrophenyl)-3-(3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (21e);   (E)-3-(3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)-1-(3-chloro-4-nitrophenyl)prop-2-en-1-one (21f);   (E)-1-(3-chloro-4-nitrophenyl)-3-(3-(3,4-dichlorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (21g);   (E)-1-(3-chloro-4-nitrophenyl)-3-(3-(3,4-difluorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (21h);   (E)-1-(3-chloro-4-nitrophenyl)-3-(3-(4-fluorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (21i);   (E)-1-(3-chloro-4-nitrophenyl)-3-(3-(4-chlorophenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (21j);   (E)-1-(3-chloro-4-nitrophenyl)-3-(3-(2-fluoro-4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (21k);   (E)-1-(3-chloro-4-nitrophenyl)-3-(3-(3,4-dimethylphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (21l);   (E)-2-((3-phenyl-1H-pyrazol-5-yl)methylene)-2,3-dihydro-1H-inden-1-one (22a);   (E)-2-((3-(4-methoxyphenyl)-1H-pyrazol-5-yl)methylene)-2,3-dihydro-1H-inden-1-one (22b);   (E)-2-((3-(3,4-dimethoxyphenyl)-1H-pyrazol-5-yl)methylene)-2,3-dihydro-1H-inden-1-one (22c);   (E)-2-((3-(3,5-dimethoxyphenyl)-1H-pyrazol-5-yl)methylene)-2,3-dihydro-1H-inden-1-one (22d);   (E)-2-((3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)methylene)-2,3-dihydro-1H-inden-1-one (22e);   (E)-2-((3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)methylene)-2,3-dihydro-1H-inden-1-one (22f);   (E)-2-((3 chlorophenyl)-1H-pyrazol-5-yl)methylene)-2,3-dihydro-1H-inden-1-one (22g);   (E)-2-((3-(3,4-difluorophenyl)-1H-pyrazol-5-yl)methylene)-2,3-dihydro-1H-inden-1-one (22h);   (E)-2-((3-(4-fluorophenyl)-1H-pyrazol-5-yl)methylene)-2,3-dihydro-1H-inden-1-one (22i);   (E)-2-((3-(4-chlorophenyl)-1H-pyrazol-5-yl)methylene)-2,3-dihydro-1H-inden-1-one (22j);   (E)-2-((3-(2-fluoro-4-methoxyphenyl)-1H-pyrazol-5-yl)methylene)-2,3-dihydro-1H-inden-1-one (22k);   (E)-2-((3-(3,4-dimethylphenyl)-1H-pyrazol-5-yl)methylene)-2,3-dihydro-1H-inden-1-one (22l);   (E)-5-methoxy-2-((3-phenyl-1H-pyrazol-5-yl)methylene)-2,3-dihydro-1H-inden-1-one (23a);   (E)-5-methoxy-2-((3-(4-methoxyphenyl)-1H-pyrazol-5-yl)methylene)-2,3-dihydro-1H-inden-1-one (23b);   (E)-2-((3-(3,4-dimethoxyphenyl)-1H-pyrazol-5-yl)methylene)-5-methoxy-2,3-dihydro-1H-inden-1-one (23c);   (E)-2-((3-(3,5-dimethoxyphenyl)-1H-pyrazol-5-yl)methylene)-5-methoxy-2,3-dihydro-1H-inden-1-one (23d);   (E)-5-methoxy-2-((3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)methylene)-2,3-dihydro-1H-inden-1-one (23e);   (E)-2-((3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)methylene)-5-methoxy-2,3-dihydro-1H-inden-1-one (23f);   (E)-2-((3-(3,4-dichlorophenyl)-1H-pyrazol-5-yl)methylene)-5-methoxy-2,3-dihydro-1H-inden-1-one (23g);   (E)-2-((3-(3,4-difluorophenyl)-1H-pyrazol-5-yl)methylene)-5-methoxy-2,3-dihydro-1H-inden-1-one (23h);   (E)-2-((3-(4-fluorophenyl)-1H-pyrazol-5-yl)methylene)-5-methoxy-2,3-dihydro-1H-inden-1-one (23i);   (E)-2-((3-(4-chlorophenyl)-1H-pyrazol-5-yl)methylene)-5-methoxy-2,3-dihydro-1H-inden-1-one (23j);   (E)-2-((3-(2-fluoro-4-methoxyphenyl)-1H-pyrazol-5-yl)methylene)-5-methoxy-2,3-dihydro-1H-inden-1-one (23k);   (E)-2-((3-(3,4-dimethylphenyl)-1H-pyrazol-5-yl)methylene)-5-methoxy-2,3-dihydro-1H-inden-1-one (23l);   (E)-5,6-dimethoxy-2-((3-phenyl-1H-pyrazol-5-yl)methylene)-2,3-dihydro-1H-inden-1-one (24a);   (E)-5,6-dimethoxy-2-((3-(4-methoxyphenyl)-1H-pyrazol-5-yl)methylene)-2,3-dihydro-1H-inden-1-one (24b);   (E)-2-((3-(3,4-dimethoxyphenyl)-1H-pyrazol-5-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one (24c);   (E)-2-((3-(3,5-dimethoxyphenyl)-1H-pyrazol-5-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one (24d);   (E)-5,6-dimethoxy-2-((3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)methylene)-2,3-dihydro-1H-inden-1-one (24e);   (E)-2-((3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one (24f);   (E)-2-((3-(3,4-dichlorophenyl)-1H-pyrazol-5-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one (24g);   (E)-2-((3-(3,4-difluorophenyl)-1H-pyrazol-5-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one (24h);   (E)-2-((3-(4-fluorophenyl)-1H-pyrazol-5-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one (24i);   (E)-2-((3-(4-chlorophenyl)-1H-pyrazol-5-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one (24j);   (E)-2-((3-(2-fluoro-4-methoxyphenyl)-1H-pyrazol-5-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one (24k); and   (E)-2-((3-(3,4-dimethylphenyl)-1H-pyrazol-5-yl)methylene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one (24l).   
 
         [0237]    The pyrazolochalcone of formula A is selected from the group consisting of: 
         [0000]    
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
     
         [0238]    The pyrazolochalcone of formula A for use as antitumor agent, wherein the cancer is selected from the group consisting of leukemia, non-small cell lung cancer, colon cancer, CNS cancer, melanoma, ovarian cancer, renal cancer, prostate cancer, and breast cancer. 
         [0239]    A process for the preparation of compounds of formula A, 
         [0000]    
       
                 
         
             
             
         
       
     
         [0240]    wherein, 
         [0000]    R1, R2, R3, R4, R5=H, Cl, F, CH 3 , OCH 3 , 3,4(OCH 2 O)
 
X=H, Cl, F, CH 3 , OCH 3 , 3,4(OCH 2 O), NH 2 , NO 2 , OH.
 
wherein, the process comprises reacting 3-aryl-1H-pyrazole-5-carbaldehydes of formula (5a-l)
 
         [0000]    
       
                 
         
             
             
         
       
       
         
           
             wherein R 1 , R 2 , R 3 , R 4 , R 5 =[H, Cl, F, CH 3 , OCH 3 ,3,4(OCH 2 O)]
 
with a compound selected from the group consisting of compounds of formulae a, b, c, d, e, f, g, h, i, j, k, l, m, n, o, p, q, r, or s.
 
           
         
       
     
         [0000]    
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
       
                 
         
             
             
         
       
     
         [0000]    in an alcohol in the presence of a base at a temperature ranging between 28° C. to 35° C. for a period ranging between 2 to 4 h to obtain a reaction mixture, evaporating the reaction mixture by vacuum distillation and neutralizing the residue with dil. HCl followed by extraction with water immiscible solvent; drying over anhydrous Na 2 SO 4  and evaporating the solvent to provide a crude product, purifying the product by chromatographic method using ethyl acetate/hexane as eluent to obtain the pure desired compounds of formulae: 6a-21a, 6b-21b, 6c-21c, 6d-21d, 6e-21e, 6f-21f, 6g-21g, 6h-21h, 6i-21i, 6j-21j, 6k-21k, 6l-21l and 22a-24a, 22b-24b, 22c-24c, 22d-24d, 22e-24e, 22f-24f, 22g-24g, 22h-24h, 22i-24i, 22j-24j, 22k-24k, 22l-24l. 
         [0242]    In one more embodiment of the invention the alcohol used is selected from ethanol or methanol. 
         [0243]    In a further embodiment of the invention the base used is selected from NaOH or KOH. 
         [0244]    In still further embodiment of the invention the water immiscible solvent is selected from the group consisting of ethyl acetate, chloroform or dichloromethane. 
     
    
     DETAILED DESCRIPTION OF THE INVENTION 
       [0245]    The precursors 3-phenyl-1H-pyrazole-5-carbaldehydes of formulae 5(a-l) have been prepared using literature method (Yamazaki, Y., Tanaka, K., Nicholson, B., Deyanat-Yazdi, G., Potts, B., Yoshida, T., Oda, A., Kitagawa, T., Orikasa, S., Kiso, Y., Yasui, H., Akamatsu, M., Chinen, T., Usui, T., Shinozaki, Y., Yakushiji, F., Miller, B. R., Neuteboom, S., Palladino, M., Kanoh, K., Lloyd, G. K. and Hayashi, Y. Synthesis and structure-activity relationship study of antimicrotubule agents phenylahistin derivatives with a didehydropiperazine-2,5-dione structure.  J. Med. Chem.  2012, 55, 1056-1071). The crucial intermediates for the preparation of precursors 3-phenyl-1H-pyrazole-5-carbaldehydes of formulae 5(a-l) are ethyl 3-phenyl-1H-pyrazole-5-carboxylates 4(a-l) have been prepared using literature methods (Nagarapu, L., Gaikwad, H. K., Sarikonda, K., Mateti, J., Bantu, R., Raghu, P. S., Manda, K. M. and Kalvendi. S. V. Synthesis and cytotoxicity evaluation of 1-[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]-3-aryl-1H-pyrazole-5-carboxylic acid derivatives. Eur. J. Med. Chem. 2010, 45, 4720-4725, Sidique, S., Ardecky, R., Su, Y., Narisawa, S., Brown, B., Millan, J. L., Sergienko, E. and Cosford, N. D., Design and synthesis of pyrazole derivatives as potent and selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP).  Bioorg. Med. Chem. Lett.  2009, 19, 222-225). 
         [0246]    These pyrazolochalcones have shown promising anticancer activity in various cell lines. The molecules synthesized are of immense biological significance. This resulted in design and synthesis of new congeners as illustrated in scheme 1 which comprises: The Claisen condensation between 3-phenyl-1H-pyrazole-5-carbaldehydes of formulae 5(a-l) and the compounds of formulae a, b, c, d, e, f, g, h, j, k, l, m, n, o, p for synthesis of the compounds (6a-21a to 6l-21l) or q, r, s for synthesis of the compounds (22a-24a to 22l-24l), respectively. 
         [0247]    The Synthesis of pyrazolochalcones described in the present invention are outlined in Scheme 1. The final step has been carried out by the application of Claisen condensation between equimolar mixture of 3-phenyl-1H-pyrazole-5-carbaldehydes formulae 5(a-l) and substituted acetophenones/indanones in the presence of base in alcohol. The key intermediates 3-substituted phenyl-1H-pyrazole-5-carbaldehydes 5(a-l) were prepared in four sequential steps. Initially substituted acetophenones 1(a-l) reacted with diethyl oxalate in the presence of sodium ethanolate in ethanol yielded ethyl 2,4-dioxo-4-(substituted phenyl)butanoates 2(a-l). This was further cyclised with NH 2 —NH 2 .2HCl in ethanol to produce ethyl 3-substituted phenyl-1H-pyrazole-5-carboxylates 3(a-l) in good yields. The obtained carboxylates were reduced to (3-substituted phenyl-1H-pyrazol-5-yl) methanols 4(a-l) by LiAlH 4 . These were selectively oxidized to 3-substituted phenyl-1H-pyrazole-5-carbaldehydes 5(a-l) by IBX in DMSO. 
         [0000]    
       
                 
         
             
             
         
       
     
         [0248]    Reagents and conditions (i) NaOEt, EtOH, 8 h, 0° C. then rt, (80-90%); (ii) NH 2 —NH 2 .2HCl, EtOH, 4 h, reflux, (72-79%); (iii) LiAlH 4 , THF, 1 h, 0° C. then rt, (65-70%); (iv) IBX, dry DMSO, 1 h, rt, (80-90%); (v) NaOH/KOH, EtOH/MeOH, acetophenones, 4 h, rt, (50-70%); (vi) NaOH/KOH, EtOH/MeOH, indanones, 2 h, rt, (50-60%). 
         [0249]    The present invention further provides a process for the preparation of new pyrazolochalcones of formulae 6a-21a, 6b-21b, 6c-21c, 6d-21d, 6e-21e, 6f-21f, 6g-21g, 6h-21h, 6i-21i, 6j-21j, 6k-21k, 6l-21l and 22a-24a, 22b-24b, 22c-24c, 22d-24d, 22e-24e, 22f-24f, 22g-24g, 22h-24h, 22i-24i, 22j-24j, 22k-24k, 22l-24l which comprises reacting 3-phenyl-1H-pyrazole-5-carbaldehydes of formula 5(a-l) with different acetophenones of formulae a, b, c, d, e, f, g, h, i, j, k, 1, m, n, o, p for synthesis of the compounds (6a-21a to 6l-21l) or q, r, s for synthesis of the compounds (22a-24a to 22l-24l) respectively, in protic water miscible solvent (ethanol or methanol) in the presence of NaOH or KOH at room temperature. The stirring continued for 4h or 2h. Solvent was removed by vacuum evaporation and the resultant residue was neutralized by using dilute HCl and extracted with ethyl acetate followed by evaporation of solvent which resulted in a crude product which was further purified by column chromatography to obtain the desired products of formulae: 6a-21a, 6b-21b, 6c-21c, 6d-21d, 6e-21e, 6f-21f, 6g-21g, 6h-21h, 6i-21i, 6j-21j, 6k-21k, 6k-21l and 22a-24a, 22b-24b, 22c-24c, 22d-24d, 22e-24e, 22f-24f, 22g-24g, 22h-24h, 22i-24i, 22j-24j, 22k-24k, 22l-24l, respectively. 
         [0000]    
       
                 
         
             
             
         
       
       
         
           
             wherein R 1 , R 2 , R 3 , R 4 , R 5 =[H, Cl, F, CH 3 , OCH 3 ,3,4(OCH 2 O)] 
           
         
       
     
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       EXAMPLES 
       [0251]    The following examples are given by way of illustration and therefore should not be construed to the present limit of the scope of invention. 
       Example 1 
     (E)-1-(4-methoxyphenyl)-3-(3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (7e) 
       [0252]    1-(4-methoxyphenyl)ethanone (b) (150 mg, 1.0 mmol) was added to 3-(3,4,5-trimethoxyphenyl)-1H-pyrazole-5-carbaldehyde (5e) (262 mg, 1.0 mmol) in ethanol (10 mL) and catalytic amount (5 mg) of sodium hydroxide (NaOH) to obtain a reaction mixture. The reaction mixture was stirred at 30° C. for 4 h and the reaction was monitored by TLC using ethyl acetate/hexane (4:6) as a solvent system. This solution was then evaporated by vacuum distillation and the residue was neutralized with dil. HCl solution which was further extracted with ethyl acetate (25 mL×4). The organic solution was dried over anhydrous Na 2 SO 4  and then the solvent was evaporated to obtain a crude product. The crude product was further purified by column chromatography using ethyl acetate/hexane (3:7) as eluent to obtain the pure compound 7e (210 mg, 53.3% yield). 
         [0253]      1 H NMR (CDCl 3 +DMSO): δ 3.77 (s, 3H), 3.88 (s, 9H), 7.13 (s, 4H), 7.40 (d, 1H, J=8.4 Hz), 7.55-7.66 (m, 1H, J=15.8 Hz, trans H), 7.77-7.96 (m, 1H, J=15.8 Hz trans H), 8.10 (d, 2H, J=8.1 Hz), 13.52 (brs, NH) ppm. FABMS: 395.M+H) + . 
       Example 2 
     (E)-1-(3,4-dimethoxyphenyl)-3-(3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (8e) 
       [0254]    1-(3,4-dimethoxyphenyl)ethanone (c) (180 mg, 1.0 mmol) was added to 3-(3,4,5-trimethoxyphenyl)-1H-pyrazole-5-carbaldehyde (5e) (262 mg, 1.0 mmol) in ethanol (10 mL) and catalytic amount (5 mg) of sodium hydroxide (NaOH) to obtain a reaction mixture. The reaction mixture was stirred at 29° C. for 4 h and the reaction was monitored by TLC using ethyl acetate/hexane (4:6) as a solvent system. This solution was then evaporated by vacuum distillation and the residue was neutralized with dil. HCl solution which was further extracted with ethyl acetate (25 mL×4). The organic solution was dried over anhydrous Na 2 SO 4  and the solvent was evaporated to obtain a crude product. The crude product was further purified by column chromatography using ethyl acetate/hexane (4:6) as eluent to obtain the pure compound 8e (225 mg, 52.9% yield). 
         [0255]      1 H NMR (CDCl 3 +DMSO-d 6 ): δ 3.70 (s, 3H), 3.76 (s, 6H), 3.88 (s, 6H), 7.06-7.18 (m, 3H), 7.39 (d, 2H, J=14.9 Hz), 7.56-7.62 (m, 1H), 7.65 (d, 1H, J=7.7 Hz), 7.79-7.97 (m, 2H, J=15.6 Hz) ppm; FABMS: 425M+H) + . 
       Example 3 
     (E)-1-(3,4,5-trimethoxyphenyl)-3-(3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (10e) 
       [0256]    1-(3,4,5-trimethoxyphenyl)ethanone (e) (210 mg, 1.0 mmol) was added to 3-(3,4,5-trimethoxyphenyl)-1H-pyrazole-5-carbaldehyde (5e) (262 mg, 1.0 mmol) in ethanol (10 mL) and catalytic amount (5 mg) of sodium hydroxide (NaOH) to obtain a reaction mixture. The reaction mixture was stirred at 32° C. for 4 h and the reaction was monitored by TLC using ethyl acetate/hexane (4:6) as a solvent system. This solution was then evaporated by vacuum distillation and the residue was neutralized with dil. HCl solution which was further extracted with ethyl acetate (25 mL×4). The organic solution was dried over anhydrous Na 2 SO 4  and the solvent was evaporated to obtain a crude product. The crude product was further purified by column chromatography using ethyl acetate/hexane (4:6) as eluent to obtain the pure compound 10e (285 mg, 62.7% yield). 
         [0257]      1 H NMR (CDCl 3 +DMSO-d 6 ): δ 3.74-4.00 (m, 18H), 6.85 (s, 1H), 6.90 (s, 1H), 7.25 (d, 2H, J=4.7 Hz), 7.36 (s, 1H), 7.55 (d, 1H J=15.8 Hz), 7.76 (d, 1H, J=15.6 Hz) ppm; FABMS: 455M+H) + . 
       Example 4 
     (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (11e) 
       [0258]    1-(benzo[d][1,3]dioxol-5-yl)ethanone (f) (164 mg, 1.0 mmol) was added to 3-(3,4,5-trimethoxyphenyl)-1H-pyrazole-5-carbaldehyde (5e) (262 mg, 1.0 mmol) in ethanol (10 mL) and catalytic amount (5 mg) of sodium hydroxide (NaOH) to obtain a reaction mixture. The reaction mixture was stirred at 30° C. for 4 h and the reaction was monitored by TLC using ethyl acetate/hexane (4:6) as a solvent system. This solution was then evaporated by vacuum distillation and the residue was neutralized with dil. HCl solution which was further extracted with ethyl acetate (25 mL×4). The organic solution was dried over anhydrous Na 2 SO 4  and the solvent was evaporated to obtain a crude product. The crude product was further purified by column chromatography using ethyl acetate/hexane (3:7) as eluent to obtain the pure compound 11e (260 mg, 63.6% yield). 
         [0259]      1 H NMR (CDCl 3 +DMSO-d 6 ): δ 3.81 (s, 3H), 3.92 (s, 6H), 6.96 (d, 1H, J=13.8 trans H), 7.08 (s, 2H), 7.55 (s, 1H), 7.69 (s, 1H), 7.73 (d, 1H J=16.8 Hz), 7.81-7.85 (m, 1H) ppm; FABMS: 409M+H) + . 
       Example 5 
     (E)-1-(3,4-dichlorophenyl)-3-(3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (12e) 
       [0260]    1-(3,4-dichlorophenyl)ethanone (g) (189 mg, 1.0 mmol) was added to 3-(3,4,5-trimethoxyphenyl)-1H-pyrazole-5-carbaldehyde (5e) (262 mg, 1.0 mmol) in ethanol (10 mL) and catalytic amount (5 mg) of sodium hydroxide (NaOH) to obtain a reaction mixture. The reaction mixture was stirred at 32° C. for 4 h and the reaction was monitored by TLC using ethyl acetate/hexane (4:6) as a solvent system. This solution was then evaporated by vacuum distillation and the residue was neutralized with dil. HCl solution which was further extracted with ethyl acetate (25 mL×4). The organic solution was dried over anhydrous Na 2 SO 4  and the solvent was evaporated to obtain a crude product. The crude product was further purified by column chromatography using ethyl acetate/hexane (3:7) as eluent to obtain the pure compound 12e (210 mg, 53.3% yield). 
         [0261]      1 H NMR (CDCl 3 ): □δ 3.85 (s, 3H), 3.94 (s, 6H), 3.99 (s, 3H) 6.89 (s, 1H) 7.06 (s, 2H), 7.12 (d, 1H, J=8.4 Hz), 7.49-7.55 (m, 2H), 7.67-7.95 (m, 2H J=15.4, 16.8 Hz) ppm; FABMS: 434M+H) + . 
       Example 6 
     (E)-1-(3,4-difluorophenyl)-3-(3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (13e) 
       [0262]    1-(3,4-difluorophenyl)ethanone (h) (156 mg, 1.0 mmol) was added to 3-(3,4,5-trimethoxyphenyl)-1H-pyrazole-5-carbaldehyde (5e) (262 mg, 1.0 mmol) in ethanol (10 mL) and catalytic amount (5 mg) of sodium hydroxide (NaOH) to obtain a reaction mixture. The reaction mixture was stirred at 28° C. for 4 h and the reaction was monitored by TLC using ethyl acetate/hexane (4:6) as a solvent system. This solution was then evaporated by vacuum distillation and the residue was neutralized with dil. HCl solution which was further extracted with ethyl acetate (25 mL×4). The organic solution was dried over anhydrous Na 2 SO 4  and the solvent was evaporated to obtain a crude product. The crude product was further purified by column chromatography using ethyl acetate/hexane (3:7) as eluent to obtain the pure compound 13e (280 mg, 69.9% yield). 
         [0263]      1 H NMR (CDCl 3 +DMSO-d 6 ): δ3.83 (s, 6H), 3.84 (s, 3H), 5.90 (s, 1H) 6.19 (s, 1H) 6.54 (s, 1H), 6.85-7.02 (m, 1HJ=16.6 Hz), 7.06-7.16 (m, 1H), 7.23-7.33 (m, 2H), 7.33-7.55 (m, 1H J=16.8 Hz) ppm; FABMS: 401M+Hr. 
       Example 7 
     (E)-3-(3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one (8f) 
       [0264]    1-(3,4-dimethoxyphenyl)ethanone (c) (180 mg, 1.0 mmol) was added to 3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazole-5-carbaldehyde (5f) (216 mg, 1.0 mmol) in ethanol (10 mL) and catalytic amount (5 mg) of sodium hydroxide (NaOH) to obtain a reaction mixture. The reaction mixture was stirred at 34° C. for 4 h and the reaction was monitored by TLC using ethyl acetate/hexane (4:6) as a solvent system. This solution was then evaporated by vacuum distillation and the residue was neutralized with dil. HCl solution which was further extracted with ethyl acetate (25 mL×4). The organic solution was dried over anhydrous Na 2 SO 4  and the solvent was evaporated to obtain a crude product. The crude product was further purified by column chromatography using ethyl acetate/hexane (4:6) as eluent to obtain the pure compound 8f (262 mg, 69.2% yield). 
         [0265]      1 H NMR (CDCl 3 +DMSO-d 6 ): δ 3.86 (s, 3H), 3.89 (s, 3H), 6.07 (s, 2H), 6.94-7.08 (m, 1H), 7.15 (d, 1H, J=8.4), 7.25-7.38 (m, 2H J=16.8), 7.54-7.64 (m, 2H J=15.4, 16.8 Hz), 7.84 (d, 2H J=8.4 Hz), 13.45 (brs, NH) ppm; FABMS: 379M+H) + . 
       Example 8 
     (E)-5-methoxy-2-((3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)methylene)-2,3-dihydro-1H-inden-1-one (23e) 
       [0266]    5-methoxy-2,3-dihydro-1H-inden-1-one (r) (162 mg, 1.0 mmol) was added to 3-(3,4,5-trimethoxyphenyl)-1H-pyrazole-5-carbaldehyde (5e) (262 mg, 1.0 mmol) in ethanol (10 mL) and catalytic amount (5 mg) of sodium hydroxide (NaOH) to obtain a reaction mixture. The reaction mixture was stirred at 35° C. for 2 h and the reaction was monitored by TLC using ethyl acetate/hexane (4:6) as a solvent system. This solution was then evaporated by vacuum distillation and the residue was neutralized with dil. 
         [0267]    HCl solution which was further extracted with ethyl acetate (25 mL×4). The organic solution was dried over anhydrous Na 2 SO 4  and the solvent was evaporated to obtain a crude product. The crude product was further purified by column chromatography using ethyl acetate/hexane (4:6) as eluent to obtain the pure compound 23e (274 mg, 67.4% yield). 
         [0268]      1 H NMR (CDCl 3 ): δ=1.25 (s, 2H), 2.36 (s, 3H), 3.94 (s, 6H), 4.01 (s, 3H), 6.80 (s, 1H), 6.91-6.99 (m, 1H), 7.07 (s, 2H) 7.57 (d, 2H, J=8.4 Hz) ppm; FABMS: 407M+H) + . 
       Example 9 
     (E)-1-(4-aminophenyl)-3-(3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-one (19e) 
       [0269]    1-(4-aminophenyl)ethanone (n) (135 mg, 1.0 mmol) was added to 3-(3,4,5-trimethoxyphenyl)-1H-pyrazole-5-carbaldehyde (5e) (262 mg, 1.0 mmol) in ethanol (10 mL) and catalytic amount (5 mg) of sodium hydroxide (NaOH) to obtain a reaction mixture. The reaction mixture was stirred at 28° C. for 4 h and the reaction was monitored by TLC using ethyl acetate/hexane (4:6) as a solvent system. This solution was then evaporated by vacuum distillation and the residue was neutralized with dil. HCl solution which was further extracted with ethyl acetate (25 mL×4). The organic solution was dried over anhydrous Na 2 SO 4  and the solvent was evaporated to obtain a crude product. The crude product was further purified by column chromatography using ethyl acetate/hexane (3:7) as eluent to obtain the pure compound 19e (264 mg, 64.8% yield). 
         [0270]      1 H NMR (CDCl 3 ): δ 3.77 (s, 3H), 3.85 (s, 6H), 4.74 (brs, NH), 6.62 (d, 2H, J=8.9 Hz), 6.75 (s, 1H), 6.97 (s, 2H) 7.37 (s, 1H) 7.55-7.66 (m, 2H, J=15.8 Hz), 7.84 (d, 2H, J=8.4 Hz) ppm; FABMS: 380M+H) + . 
       Example 10 
     (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)prop-2-en-1-one (11f) 
       [0271]    1-(benzo[d][1,3]dioxol-5-yl)ethanone (f) (164 mg, 1.0 mmol) was added to 3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazole-5-carbaldehyde (5f) (216 mg, 1.0 mmol) in ethanol (10 mL) and catalytic amount (5 mg) of sodium hydroxide (NaOH) to obtain a reaction mixture. The reaction mixture was stirred at 30° C. for 4 h and the reaction was monitored by TLC using ethyl acetate/hexane (4:6) as a solvent system. This solution was then evaporated by vacuum distillation and the residue was neutralized with dil. HCl solution which was further extracted with ethyl acetate (25 mL×4). The organic solution was dried over anhydrous Na 2 SO 4  and the solvent was evaporated to obtain a crude product. The crude product was further purified by column chromatography using ethyl acetate/hexane (3:7) as eluent to obtain the pure compound 11f (227 mg, 62.6% yield). 
         [0272]      1 H NMR (CDCl 3 +DMSO-d6): δ 6.03 (s, 2H), 6.13 (s, 2H), 6.87 (d, 1H J=8.0 Hz), 6.99 (d, 1H, J==8.4), 7.03 (s, 1H), 7.30 (d, 1H, J=8.1 Hz), 7.56 (s, 1H), 7.64 (d, 1H, J=15.4 Hz), 7.72-7.79 (m, 2H, J=15.2 Hz) 8.04 (s, 1H) ppm; FABMS: 363M+H) + . 
       Example 11 
     (E)-3-(3-(4-methoxyphenyl)-1H-pyrazol-5-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (10b) 
       [0273]    1-(3,4,5-trimethoxyphenyl)ethanone (e) (210 mg, 1.0 mmol) was added to 3-(4-methoxyphenyl)-1H-pyrazole-5-carbaldehyde (5b) (202 mg, 1.0 mmol) in methanol (10 mL) and catalytic amount (5 mg) of potassium hydroxide (KOH) to obtain a reaction mixture. The reaction mixture was stirred at 34° C. for 4 h and the reaction was monitored by TLC using ethyl acetate/hexane (3:7) as a solvent system. This solution was then evaporated by vacuum distillation and the residue was neutralized with dil. HCl solution which was further extracted with ethyl acetate (25 mL×4). The organic solution was dried over anhydrous Na 2 SO 4  and the solvent was evaporated to obtain a crude product. The crude product was further purified by column chromatography using ethyl acetate/hexane (3:7) as eluent to obtain the pure compound 10b (250 mg, 64.7% yield). 
         [0274]      1 H NMR (CDCl 3 +DMSO-d6): δ 3.75 (s, 3H), 3.80 (s, 3H), 3.87 (s, 6H), 6.81 (s, 1H), 6.86 (d, 2H) J=8.4 Hz), 7.26 (s, 2H), 7.55-7.69 (m, 4H, J=15.8 Hz J=8.4 Hz) ppm; FABMS: 395M+H) + . 
       Example 12 
     (E)-3-(3-(3,4-dimethoxyphenyl)-1H-pyrazol-5-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (10c) 
       [0275]    1-(3,4,5-trimethoxyphenyl)ethanone (e) (210 mg, 1.0 mmol) was added to 3-(3,4-dimethoxyphenyl)-1H-pyrazole-5-carbaldehyde (5c) (202 mg, 1.0 mmol) in methanol (10 mL) and catalytic amount (5 mg) of potassium hydroxide (KOH) to obtain a reaction mixture. The reaction mixture was stirred at 35° C. for 4 h and the reaction was monitored by TLC using ethyl acetate/hexane (4:6) as a solvent system. This solution was then evaporated by vacuum distillation and the residue was neutralized with dil. HCl solution which was further extracted with ethyl acetate (25 mL×4). The organic solution was dried over anhydrous Na 2 SO 4  and the solvent was evaporated to obtain a crude product. The crude product was further purified by column chromatography using ethyl acetate/hexane (3:7) as eluent to obtain the pure compound 10c (280 mg, 66% yield). 
         [0276]      1 H NMR (CDCl 3 +DMSO-d6): δ 3.92 (s, 3H), 3.93 (s, 3H), 3.97 (s, 6H), 6.86 (s, 1H), 6.94 (d, 1H) J=8.3 Hz), 7.31-7.42 (m, 3H), 7.42-7.53 (m, 2H), 7.65 (d, 1H, trans J=15.8 Hz), 7.79 (d, 1H, trans J=15.8 Hz) ppm; FABMS: 425M+H) + . 
       Example 13 
     (E)-1-(4-aminophenyl)-3-(3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)prop-2-en-1-one (19f) 
       [0277]    1-(4-aminophenyl)ethanone (n) (135 mg, 1.0 mmol) was added to 3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazole-5-carbaldehyde (5f) (216 mg, 1.0 mmol) in ethanol (10 mL) and catalytic amount (5 mg) of potassium hydroxide (KOH) to obtain a reaction mixture. The reaction mixture was stirred at 30° C. for 4 h and the reaction was monitored by TLC using ethyl acetate/hexane (3:6) as a solvent system. This solution was then evaporated by vacuum distillation and the residue was neutralized with dil. HCl solution which was further extracted with ethyl acetate (25 mL×4). The organic solution was dried over anhydrous Na 2 SO 4  and the solvent was evaporated to obtain a crude product. The crude product was further purified by column chromatography using ethyl acetate/hexane (3:7) as eluent to obtain the pure compound 19f (210 mg, 63% yield). 
         [0278]      1 H NMR (CDCl 3 +DMSO-d6): δ 5.51 (brs, 2H), 6.02 (s, 2H), 6.69 (d, 2H, J=8.3 Hz), 6.8-6.94 (m, 2H), 7.24-7.36 (m, 2H), 7.65 (d, 1H, trans J=15.8 Hz), 7.70 (d, 1H, trans J=15.8 Hz) 7.81 (s, 1H), 7.88 (d, 1H, J=8.6 Hz) ppm; FABMS: 333M+H) + . 
       Example 14 
     (E)-3-(3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (10f) 
       [0279]    1-(3,4,5-trimethoxyphenyl)ethanone (e) (210 mg, 1.0 mmol) was added to 3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazole-5-carbaldehyde (5f) (216 mg, 1.0 mmol) in methanol (10 mL) and catalytic amount (5 mg) of sodium hydroxide (NaOH) to obtain a reaction mixture. The reaction mixture was stirred at 34° C. for 4 h and the reaction was monitored by TLC using ethyl acetate/hexane (4:6) as a solvent system. This solution was then evaporated by vacuum distillation and the residue was neutralized with dil. HCl solution which was further extracted with ethyl acetate (25 mL×4). The organic solution was dried over anhydrous Na 2 SO 4  and the solvent was evaporated to obtain a crude product. The crude product was further purified by column chromatography using ethyl acetate/hexane (3:7) as eluent to obtain the pure compound 10f (225 mg, 55% yield). 
         [0280]      1 H NMR (CDCl 3 +DMSO-d6): δ 3.9 (s, 3H), 3.96 (s, 6H), 6.01 (s, 2H), 6.82-6.92 (m, 2H), 7.27-7.37 (m, 3H, J 1 =8.3 Hz, trans J 2 =15.8 Hz), 7.66-7.76 (m, 2H, J j =8.3 Hz, trans J 2 =15.8 Hz) ppm; FABMS: 409M+H) + . 
       Example 15 
     (E)-1-(3,4-dimethoxyphenyl)-3-(3-(4-methoxyphenyl)-1H-pyrazol-5-yl)prop-2-en-1-ine (8b) 
       [0281]    1-(3,4-dimethoxyphenyl)ethanone (c) (180 mg, 1.0 mmol) was added to 3-(4-methoxyphenyl)-1H-pyrazole-5-carbaldehyde (5b) (202 mg, 1.0 mmol) in ethanol (10 mL) and catalytic amount (5 mg) of sodium hydroxide (NaOH) to obtain a reaction mixture. The reaction mixture was stirred at 30° C. for 4 h and the reaction was monitored by TLC using ethyl acetate/hexane (4:6) as a solvent system. This solution was then evaporated by vacuum distillation and the residue was neutralized with dil. HCl solution which was further extracted with ethyl acetate (25 mL×4). The organic solution was dried over anhydrous Na 2 SO 4  and the solvent was evaporated to obtain a crude product. The crude product was further purified by column chromatography using ethyl acetate/hexane (3:7) as eluent to obtain the pure compound 8b (215 mg, 59% yield). 
         [0282]      1 H NMR (CDCl 3 +DMSO-d6): δ 3.76 (s, 3H), 3.87 (s, 6H), 6.76-6.90 (m, 3H), 6.90-6.99 (m, 1H), 7.53 (s, 1H), 7.58-7.75 (m, 4H, J 1 =8.4 Hz, trans J 2 =15.8 Hz), 7.83 (s, 1H) ppm; FABMS: 365M+H) + . 
       Anticancer Activity: 
       [0283]    Some of in vitro biological activity studies were carried out at the National Cancer Institute, Maryland, USA. 
       In Vitro Cytotoxicity 
       [0284]    The pyrazolochalcones (7e, 8e, 10e, 11e, 12e, 13e and 8f) have been tested against fifty nine human tumor cell lines derived from nine cancer types (leukemia, non-small cell lung cancer, colon cancer, CNS cancer, melanoma, ovarian cancer, renal cancer, prostate cancer and breast cancer) as per the NCI protocol. For each compound, dose response curves for individual cell lines have been measured at a minimum of five concentrations at 10 fold dilutions. A protocol of 48 h continuous drug exposure has been used, and a sulforhodamine B (SRB) protein assay has been used to estimate cell viability or growth. The concentration for 50% cell growth inhibition (GI 50 ), 50% cell death (LC 50 , 50% growth) and total cell growth inhibition (TGI, 0% growth) values were tabulated (Table-1). DMSO was used as control to calculate the values of GI 50 , LC 50  and TGI. The compounds 7e, 8e, 10e, 11e, 12e, 13e and 8f has been evaluated for their in vitro cytotoxicity in sixty cell lines from nine human cancer types of leukemia (K-562, SR), non-small cell lung (Hop-62, NCI-H226, NCI-H522), colon (HCT-116, HCT-15, HCC-2998), CNS (SF-539), melanoma (SK-MEL-5, UACC-62, M14), ovarian (IGROV1), renal (A498), prostate (PC3) and breast (BT-549, MDA-MB-435, HS578T) origin. The results are expressed as percent of cell growth determined relative to that of untreated control cells (Table 2). The representative compounds 7e, 8e, 10e, 11e, 12e, 13e and 8f showed significant cytotoxicity against some cancer cell lines. 
         [0000]    
       
         
               
             
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
             
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
             
           
               
                 TABLE 1 
               
               
                   
               
               
                 Log 10  GI 50  (concentration in mol/L causing 50% growth inhibition) 
               
               
                 and Log 10  LC 50  (concentration in mol/L causing 50% cell death) and 
               
               
                 Log 10  TGI (concentration in mol/L causing 0% growth inhibition) values 
               
               
                 for pyrazolochalcones (7e, 8e, 10e, 11e, 12e, 13e and 8f) 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                   
                 Log 10  GI 50   
                 Log 10  LC 50   
               
             
          
           
               
                 Cell Lines 
                 7e 
                 8e 
                 10e 
                 11e 
                 12e 
                 13e 
                 8f 
                 7e 
                 8e 
                 10e 
                 11e 
               
               
                   
               
               
                 Leukemia 
                 −5.92 
                 −6.1 
                 −5.92 
                 −4.91 
                 −5.68 
                 −5.57 
                 −5.69 
                 −4 
                 −4.01 
                 −4 
                 −4 
               
               
                 Non-small cell lung 
                 −5.74 
                 −5.91 
                 −5.89 
                 −4.27 
                 −5.18 
                 −5.54 
                 −5.6 
                 −4.66 
                 −5.19 
                 −4.87 
                 −4.27 
               
               
                 Colon 
                 −5.76 
                 −5.85 
                 −5.79 
                 −4.66 
                 −5.32 
                 −5.52 
                 −5.52 
                 −4.72 
                 −5.21 
                 −5.22 
                 −4.66 
               
               
                 CNS 
                 −5.78 
                 −5.85 
                 −5.79 
                 −4.2 
                 −5.07 
                 −5.47 
                 −5.65 
                 −4.61 
                 −5.21 
                 −5.1 
                 −4.2 
               
               
                 Melanoma 
                 −5.68 
                 −5.77 
                 −5.77 
                 −4.14 
                 −4.88 
                 −5.56 
                 −5.79 
                 −4.44 
                 −5.21 
                 −5.19 
                 −4.14 
               
               
                 Ovarian 
                 −5.62 
                 −5.68 
                 −5.66 
                 −4 
                 −5 
                 −5.5 
                 −5.58 
                 −4.32 
                 −4.82 
                 −4.84 
                 −4 
               
               
                 Renal 
                 −5.74 
                 −5.82 
                 −5.8 
                 −4.37 
                 −5.05 
                 −5.56 
                 −5.46 
                 −4.74 
                 −5.18 
                 −5.12 
                 −4.37 
               
               
                 Prostate 
                 −5.83 
                 −6.06 
                 −5.83 
                 −4 
                 −5.23 
                 −5.78 
                 −5.66 
                 NT 
                 −5.28 
                 −5.13 
                 −4 
               
               
                 Breast 
                 −5.72 
                 −5.91 
                 −5.87 
                 −3.53 
                 −5.35 
                 −5.56 
                 −4.76 
                 −4.47 
                 −4.82 
                 −5 
                 −3.53 
               
               
                   
               
             
          
           
               
                   
                 Log 10  LC 50   
                 Log 10  TGI 
               
             
          
           
               
                   
                 Cell Lines 
                 12e 
                 13e 
                 8f 
                 7e 
                 8e 
                 10e 
                 11e 
                 12e 
                 13e 
                 8f 
               
               
                   
                   
               
               
                   
                 Leukemia 
                 −4 
                 −4 
                 −4 
                 −5.18 
                 −5.19 
                 −4.80 
                 −5.00 
                 −4.61 
                 −4.76 
                 −5.03 
               
               
                   
                 Non-small cell lung 
                 −3.7 
                 −4.06 
                 −3.29 
                 −5.36 
                 −5.58 
                 −5.42 
                 −4.70 
                 −4.52 
                 −4.75 
                 −5.08 
               
               
                   
                 Colon 
                 −4 
                 −4.23 
                 −3.17 
                 −5.41 
                 −5.52 
                 −5.50 
                 −5.33 
                 −4.34 
                 −4.70 
                 −4.85 
               
               
                   
                 CNS 
                 −4.06 
                 −4.04 
                 −3.81 
                 −5.46 
                 −5.53 
                 −5.46 
                 −4.83 
                 −4.25 
                 −4.38 
                 −5.14 
               
               
                   
                 Melanoma 
                 −4.02 
                 −4.19 
                 −2.98 
                 −5.32 
                 −5.49 
                 −5.47 
                 −4.52 
                 −4.21 
                 −5.00 
                 −4.80 
               
               
                   
                 Ovarian 
                 −4.02 
                 −4.05 
                 −4.28 
                 −5.15 
                 −5.29 
                 −5.23 
                 −4.38 
                 −4.27 
                 −4.45 
                 −4.87 
               
               
                   
                 Renal 
                 −4.03 
                 −4.03 
                 −4.49 
                 −5.43 
                 −5.51 
                 −5.45 
                 −4.94 
                 −4.22 
                 −4.71 
                 −5.01 
               
               
                   
                 Prostate 
                 −4 
                 −4 
                 −4.5 
                 −5.55 
                 −5.64 
                 −5.48 
                 −4.94 
                 −4.00 
                 −5.24 
                 −5.05 
               
               
                   
                 Breast 
                 −4 
                 −4.01 
                 −4.4 
                 −5.08 
                 −5.47 
                 −5.35 
                 −4.60 
                 −4.41 
                 −4.83 
                 −5.05 
               
               
                   
                   
               
             
          
         
       
     
         [0285]    Each cancer type represents the average of six to eight different cancer cell lines. 
         [0286]    The compounds 7e, 8e, 10e, 11e, 12e, 13e and 8f exhibited a wide spectrum of activity against fifty nine cell lines in nine cell panels, with GI 50  value range of 0.18-29.2 μM. Particularly, the compounds 7e, 8e, and 10e were more potent than the compounds 8f, 11e, 12e, 13e, against all the tested cell lines. In detail, the GI 50  values for the compound 7e against leukemia SR, RPMI-8226, and CCRF-CEM cell lines were 0.34, 0.43 and 1.42 μM, respectively. In the non-small cell lung cancer panel, the growth of HOP-62 and HOP92 cell lines were affected by compound 7e with GI 50  values as 1.76 and 1.06 μM, respectively. The GI 50  value for the compound 8e against non-small lung cancer cell line NCI-H522 is 0.18 μM, whereas the colon cancer cell line HCT-116 affected by compound 8e has GI 50  value of 0.88 μM. The GI 50  values for compound 8e against breast MCF7 and MDA-MB-435 cell lines were 0.82 and 0.75 μM, respectively. In the leukemia cancer panel the cell lines CCRF-CEM, RPMI-8226 and SR were affected by 8e with GI 50  values 0.62, 0.24 and 0.27 μM, respectively and the GI 50  values for the compound 8e against prostate cancer cell line DU-145 is 0.55 μM. In the non-small cell lung cancer panel, the growth of HOP-92 and NCI-H522 cell lines were affected by compound 10e with GI 50  values as 0.86 and 0.52 μM, respectively. The GI 50  values for the compound 10e against leukemia RPMI-8226 and SR are 0.31 and 0.39 μM, respectively, whereas in the breast cancer cell line MCF-7, the growth was affected by 10e with GI 50  value 0.64 μM. The GI 50  values for the compound 11e against leukemia RPMI-8226 and SR are 0.51 and 0.55 μM, respectively. In the non-small cell lung cancer panel, the growth of NCI-H522 cell line was affected by compound 11e and 12e with GI 50  values 1.03 and 1.33 μM, respectively. The GI 50  values for the compound 12e against leukemia RPMI-8226 and SR are 0.53 and 0.39 μM, respectively. The GI 50  values for the compounds 13e and 8f against non-small cell lung cancer panel, the growth of NCI-H522 cell line were 1.57 and 1.82 μM, respectively. The GI 50  values for the compound 8f against leukemia RPMI-8226 and SR were 1.03 and 1.27 μM, respectively. Overall, the growth affected by the compounds 7e, 8e, and 10e against all the cancer cell lines with GI 50  values range 0.18-4.14 μM. 
         [0287]    Compounds 7e, 8e, 10e, 11e, 12e, 13e and 8f exhibited activity against fifty nine cell lines in nine cancer cell panels with GI 50  values of &lt;29.2 μm. In vitro cytotoxicity of compounds 7e, 8e, 10e, 11e, 12e, 13e and 8f in the selected cancer cell lines has been illustrated in Table 2. The average GI 50  values for each cancer panel of compounds 7e, 8e, 10e, 11e, 12e, 13e and 8f have been illustrated in Table 2. 
         [0000]    
       
         
               
             
               
               
             
               
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
             
           
               
                 TABLE 2 
               
             
             
               
                   
               
               
                 In vitro cytotoxicity of compounds 7e, 8e, 10e, 11e, 12e, 
               
               
                 13e and 8f in a panel of fifty nine cancer cell lines. 
               
             
          
           
               
                 Cancer panel/ 
                 GI 50  (μM) 
               
             
          
           
               
                 cell line 
                 7e 
                 8e 
                 10e 
                 11e 
                 12e 
                 13e 
                 8f 
               
               
                   
               
             
          
           
               
                 Leukemia 
                   
                   
                   
                   
                   
                   
                   
               
               
                 CCRF-CEM 
                 1.42 
                 0.62 
                 1.68 
                 1.57 
                 2.15 
                 3.80 
                 2.52 
               
               
                 HL-60(TB) 
                 2.16 
                 1.44 
                 1.93 
                 2.17 
                 7.18 
                 2.48 
                 2.82 
               
               
                 K-562 
                 2.32 
                 1.91 
                 2.96 
                 3.20 
                 4.96 
                 3.31 
                 2.47 
               
               
                 MOLT-4 
                 2.67 
                 2.11 
                 2.32 
                 2.98 
                 4.38 
                 2.72 
                 3.00 
               
               
                 RPMI-8226 
                 0.43 
                 0.24 
                 0.31 
                 0.51 
                 0.53 
                 1.76 
                 1.03 
               
               
                 SR 
                 0.34 
                 0.27 
                 0.39 
                 0.55 
                 0.39 
                 2.92 
                 1.27 
               
               
                 Non-small cell lung 
               
               
                 A549/ATCC 
                 2.27 
                 1.86 
                 2.72 
                 4.32 
                 18.7 
                 2.43 
                 2.70 
               
               
                 HOP-62 
                 1.76 
                 1.44 
                 1.46 
                 2.18 
                 1.72 
                 4.39 
                 2.08 
               
               
                 HOP92 
                 1.06 
                 NT 
                 0.86 
                 NT 
                 2.53 
                 NT 
                 2.16 
               
               
                 NCI-H226 
                 1.89 
                 1.69 
                 1.60 
                 3.31 
                 18.6 
                 3.72 
                 3.40 
               
               
                 NCI-H23 
                 3.04 
                 2.15 
                 3.04 
                 2.02 
                 23.4 
                 2.60 
                 4.12 
               
               
                 NCIH322M 
                 1.92 
                 1.52 
                 2.00 
                 3.01 
                 14.5 
                 3.37 
                 2.48 
               
               
                 NCI-H460 
                 1.72 
                 1.41 
                 1.89 
                 2.12 
                 4.9 
                 2.96 
                 1.81 
               
               
                 NCI-H522 
                 1.47 
                 0.18 
                 0.52 
                 1.03 
                 1.33 
                 1.57 
                 1.82 
               
               
                 Colon 
               
               
                 COLO-205 
                 1.73 
                 1.74 
                 1.75 
                 1.87 
                 1.26 
                 1.69 
                 3.84 
               
               
                 HCC-2998 
                 1.78 
                 2.13 
                 1.83 
                 1.95 
                 9.56 
                 3.69 
                 4.99 
               
               
                 HCT-116 
                 1.73 
                 0.88 
                 1.31 
                 1.85 
                 2.95 
                 4.00 
                 2.43 
               
               
                 HCT-15 
                 1.58 
                 1.27 
                 1.50 
                 2.12 
                 4.29 
                 3.01 
                 2.81 
               
               
                 HT29 
                 1.97 
                 1.62 
                 1.79 
                 2.18 
                 1.15 
                 2.62 
                 2.98 
               
               
                 KM12 
                 1.56 
                 1.07 
                 1.49 
                 1.76 
                 3.37 
                 3.06 
                 2.86 
               
               
                 SW-620 
                 1.62 
                 1.37 
                 1.59 
                 2.47 
                 8.63 
                 3.42 
                 2.05 
               
               
                 CNS 
               
               
                 SF-268 
                 1.99 
                 1.82 
                 1.94 
                 2.97 
                 13.7 
                 3.15 
                 2.53 
               
               
                 SF-295 
                 NT 
                 NT 
                 NT 
                 NT 
                 NT 
                 NT 
                 2.51 
               
               
                 SF-539 
                 1.62 
                 1.27 
                 1.29 
                 2.07 
                 4.31 
                 3.76 
                 1.91 
               
               
                 SNB-19 
                 1.51 
                 1.42 
                 1.66 
                 4.30 
                 9.83 
                 3.64 
                 3.20 
               
               
                 SNB-75 
                 1.49 
                 1.23 
                 1.54 
                 2.01 
                 8.70 
                 2.90 
                 1.98 
               
               
                 U251 
                 NT 
                 NT 
                 NT 
                 NT 
                 NT 
                 NT 
                 1.58 
               
               
                 Melanoma 
               
               
                 LOX IMVI 
                 1.58 
                 1.38 
                 1.52 
                 1.82 
                 3.39 
                 3.18 
                 1.97 
               
               
                 MALME-3M 
                 1.86 
                 1.99 
                 1.86 
                 4.42 
                 29.2 
                 2.96 
                 7.32 
               
               
                 M14 
                 2.20 
                 1.84 
                 1.79 
                 3.86 
                 18.2 
                 2.70 
                 6.36 
               
               
                 MDA-MB-435 
                 2.20 
                 1.34 
                 1.49 
                 2.39 
                 5.65 
                 2.88 
                 3.03 
               
               
                 SK-MEL-2 
                 4.14 
                 1.85 
                 1.96 
                 10.3 
                 13.9 
                 2.30 
                 6.93 
               
               
                 SK-MEL-28 
                 2.12 
                 1.78 
                 1.82 
                 2.48 
                 18.5 
                 5.31 
                 5.76 
               
               
                 SK-MEL-5 
                 1.72 
                 1.65 
                 1.57 
                 4.51 
                 13.4 
                 2.27 
                 6.74 
               
               
                 UACC-257 
                 1.75 
                 1.49 
                 1.57 
                 2.46 
                 16.3 
                 1.75 
                 7.06 
               
               
                 UACC-62 
                 1.85 
                 1.74 
                 1.78 
                 4.67 
                 18.8 
                 2.38 
                 4.10 
               
               
                 Ovarian 
               
               
                 IGROV1 
                 2.21 
                 1.80 
                 3.14 
                 5.00 
                 24.0 
                 3.62 
                 2.79 
               
               
                 OVCAR-3 
                 1.74 
                 1.68 
                 1.75 
                 3.38 
                 6.99 
                 2.39 
                 2.02 
               
               
                 OVCAR-4 
                 2.20 
                 2.69 
                 1.45 
                 3.80 
                 10.8 
                 2.20 
                 2.11 
               
               
                 OVCAR-5 
                 1.88 
                 1.59 
                 1.64 
                 3.37 
                 20.5 
                 4.48 
                 3.36 
               
               
                 OVCAR-8 
                 2.43 
                 1.32 
                 1.58 
                 2.85 
                 6.30 
                 2.88 
                 2.15 
               
               
                 NCI/ADR-RES 
                 2.7 
                 3.13 
                 3.47 
                 4.23 
                 10.6 
                 3.46 
                 NT 
               
               
                 SK-OV-3 
                 3.99 
                 2.79 
                 3.20 
                 5.76 
                 4.19 
                 3.53 
                 3.97 
               
               
                 Renal 
               
               
                 786-0 
                 1.95 
                 1.40 
                 1.56 
                 2.33 
                 10.1 
                 3.35 
                 3.12 
               
               
                 A498 
                 1.74 
                 1.48 
                 1.61 
                 2.76 
                 5.89 
                 2.11 
                 1.55 
               
               
                 ACHN 
                 1.96 
                 1.66 
                 1.62 
                 1.88 
                 21.4 
                 3.26 
                 3.49 
               
               
                 CAKI-1 
                 2.34 
                 2.20 
                 2.58 
                 5.51 
                 16.9 
                 2.98 
                 1.90 
               
               
                 RXF 393 
                 1.27 
                 1.35 
                 1.26 
                 1.48 
                 2.70 
                 2.05 
                 2.42 
               
               
                 SN12C 
                 1.81 
                 1.54 
                 1.47 
                 3.94 
                 13.7 
                 3.37 
                 3.25 
               
               
                 TK-10 
                 2.22 
                 1.33 
                 1.46 
                 2.33 
                 8.34 
                 2.29 
                 2.8 
               
               
                 UO-31 
                 1.45 
                 1.28 
                 1.19 
                 1.91 
                 5.73 
                 2.63 
                 2.3 
               
               
                 Prostate 
               
               
                 PC-3 
                 1.51 
                 1.36 
                 1.47 
                 2.81 
                 5.95 
                 1.66 
                 2.5 
               
               
                 DU-145 
                 1.43 
                 0.55 
                 NT 
                 2.72 
                 NT 
                 NT 
                 1.8 
               
               
                 Breast 
               
               
                 MCF7 
                 1.15 
                 0.82 
                 0.64 
                 1.67 
                 1.80 
                 3.20 
                 3.2 
               
               
                 MDA-MB-231/ATCC 
                 1.88 
                 1.48 
                 1.52 
                 3.50 
                 8.65 
                 1.64 
                 2.4 
               
               
                 HS 578T 
                 3.60 
                 2.57 
                 2.68 
                 3.71 
                 16.6 
                 3.58 
                 2.6 
               
               
                 BT-549 
                 1.86 
                 1.44 
                 1.57 
                 2.37 
                 8.40 
                 4.11 
                 1.9 
               
               
                 T-47D 
                 2.31 
                 1.63 
                 1.13 
                 2.51 
                 1.66 
                 2.45 
                 3.2 
               
               
                 MDA-MB-435 
                 1.29 
                 0.75 
                 1.15 
                 1.40 
                 1.98 
                 2.22 
                 1.8 
               
               
                   
               
               
                 *NT = not tested 
               
             
          
         
       
     
         [0288]    The mean graph midpoint values of Log 10  TGI and Log 10  LC 50  as well as Log 10  GI 50  for compounds 7e, 8e, 10e, 11e, 12e, 13e and 8f is listed in Table-3. As demonstrated by mean graph pattern, compounds 7e, 8e, 10e, 11e, 12e, 13e and 8f exhibited an interesting profile of activity and selectivity for various cell lines. The mean graph mid points of Log 10  TGI and Log 10 , LC 50  have shown similar pattern to the log 10  GI 50  mean graph mid points. 
         [0000]    
       
         
               
             
               
               
               
               
               
             
           
               
                 TABLE 3 
               
             
             
               
                   
               
               
                 Log 10  GI 50,  Log 10  TGI and Log 10  LC 50  mean graphs midpoints 
               
               
                 (MG_MID) of in vitro cytotoxicity data for the compound 
               
               
                 7e, 8e, 10e, 11e, 12e, 13e and 8f against human tumor cell lines. 
               
             
          
           
               
                   
                 Compound 
                 Log 10  GI 50   
                 Log 10  TGI 
                 Log 10  LC 50   
               
               
                   
                   
               
               
                   
                 7e 
                 −5.75 
                 −5.31 
                 −4.47 
               
               
                   
                 8e 
                 −5.87 
                 −5.47 
                 −4.98 
               
               
                   
                 10e 
                 −5.81 
                 −5.36 
                 −4.94 
               
               
                   
                 11e 
                 −5.57 
                 −4.77 
                 −4.21 
               
               
                   
                 12e 
                 −5.18 
                 −4.35 
                 −4.05 
               
               
                   
                 13e 
                 −5.55 
                 −4.74 
                 −4.09 
               
               
                   
                 8f 
                 −5.56 
                 −4.98 
                 −4.36 
               
               
                   
                   
               
             
          
         
       
     
       Significance of the Work Carried Out 
       [0289]    The new pyrazolochalcones that have been synthesized exhibited significant cytotoxicity against fifty nine human tumor cell lines. 
       Advantages of the Invention 
       [0290]    1. The present invention provides a new pyrazolochalcones useful as antitumor agents.
 
2. It also provides a process for the preparation of novel pyrazolochalcones.