4-methyl-N-[5-[Phenylamino]Acetyl]-2-yl]Benzenesulfonamides: Synthesis, Characterization, and Preliminary Biological Evaluation
Authors: Sharma Himanchal , Singh Atul Pratap , Hak Jiyaul , Pathak Divya , Taumar Dhananjay , Gujjar Anshu , Chaudhary Vatan , Jahan Iram 
Published: October 2024

Introduction:

Oxazole and the compounds containing sulphonamides are utilized
for various treatments of microbial disease as well as for diabetic patients. In the current study,
the above moiety synthesizes the new molecule for the treatment of diabetes and microbial
infection. The present work involved oxazole-based sulphonamide derivatives by the N-acylation
and N-sulphonation. The synthesis was carried out by treating substituted anilines with chloroacetic
chloride. The cycloaddition reaction was carried out using triethyl amine as a base catalyst.
In the final steps, toluene sulphonyl chloride was used for sulphonation. The synthesized
substance was confirmed via IR, 1H NMR, ESI, Mass spectroscopy, and elemental investigation
technique.

Material and Methods:

Every reagent and starting material used in the synthesis was pure
enough to be used as a reagent. To provide an inert environment, the solvents were purified in
accordance with conventional laboratory protocols under a nitrogen atmosphere. Melting points
are expressed in degrees Celsius and are uncorrected. They were determined by the open capillary
technique. KBr pellets and a Shimadzu 8201 PC FTIR spectrophotometer were used to obtain
FTIR spectra. Using JEOL and Bruker 500 MHz NMR spectrometers, ~1H and ~13C NMR spectra
were obtained in CDCl3 and DMSO-d6, with TMS serving as the internal reference. A Thermo-
Finnigan mass spectrophotometer was used to determine the masses of the chemical using the
ESI technique.

Result:

The present work involved oxazole-based sulphonamides derivatives by the N-acylation
and N-sulphonation. The synthesis was carried out by treating substituted anilines with chloroacetic
chloride. The cycloaddition reaction was carried out using triethyl amine as a base catalyst. In
the final steps, toluene sulphonyl chloride was used for sulphonation. IR, 1HNMR, ESI, Mass
spectroscopy and elemental analysis technique confirmed the synthesized compound.

Discussion:

Oxazoles are also related to compounds called 1,3-azoles[nitrogen and oxygen heteroatoms
in a 5-membered ring]. Oxazole demonstrates aromaticity since Huckel's rule requires
6π electrons, which are provided by the delocalization of a single pair of electrons from the oxygen
atom. It has a wide range of pharmacological aspects like anti-allergic, hypertension, inflammation,
schizophrenia, and inflammation. Similarly, sulphonamides are also used as preventive
and chemotherapeutic agents against various diseases such as antibacterial, antiprotozoal, antifungal,
and translation initiation inhibitors.

Conclusion:

The preliminary biological activity was performed on a preliminary level for the
antimicrobial and antidiabetic profile. The disc diffusion approach was utilized to achieve the
antibacterial activity; similarly diabetic activity was carried out by the induced method. Out of all
the synthesized compounds N-[5-[2-[4-bromophenyl amino]acetyloxazole2 yl]-4methylo benzene
sulphonamide [4a], N-[5-2[2-FLoro-5nitrophenyl amino]acetyloxazole2yl]-4methylo benzene
sulfonamide [4b] show significant effect compared to standard drugs.