bluuebunny/crossref_metadata_2025 huggingface dataset:
The COMT Val158Met polymorphism and cognition in depressed and nondepressed older adults
Authors: Potter G. G. , Taylor W. D. , McQuoid D. R. , Steffens D. C. , Welsh‐Bohmer K. A. , Krishnan K. R. R.
Published: March 2009

Objective

The objective of the current study was to examine the relationship between the COMT Val158Met polymorphism and neuropsychological performance in depressed and nondepressed older adults.

Methods

One hundred and twenty‐six clinically depressed older adults and 105 nondepressed comparison participants were compared on neuropsychological performance and COMT Val158Met (Val/Val, Val/Met, Met/Met).

Results

Based on multivariate regression models, the COMT Val158Met polymorphism was not associated with cognitive performance among depressed or nondepressed individuals, nor did this polymorphism account for the fact that depressed individuals performed worse than nondepressed individuals on several neuropsychological tests that are typically affected by depression. There was also no difference in frequency of the COMT Val158Met alleles between depressed and nondepressed individuals.

Conclusions

Although the current study found no association between COMT Val158Met polymorphism on a number of clinical neuropsychological tests that are typically found to be sensitive to depression, differential effects of the COMT Val158Met polymorphism on dopamine transmission in psychiatric and non‐psychiatric populations may be further clarified by clinical research with neuroscience‐based paradigms that segregate cognitive tasks into component processes with precise neural substrates, particularly with respect to the complex functions of the prefrontal cortex. Negative results can be important to narrowing down target processes and understanding the influence of clinical and demographic characteristics in studies of psychiatric genetics. Copyright © 2009 John Wiley & Sons, Ltd.
Erratum: The choices, choosing model of quality of life: description and rationale
Authors: Gurland Barry J. , Gurland Roni V.
Published: March 2009

International Journal of Geriatic Psychiatry 2009; 24: 90–95
DOI: 10.1002/gps.2110

If has come to our attention that this Research Article was published with an incorrect SUMMARY. We now publish below, the entire SUMMARY as first intended.
Magnetoencephalographic gamma power reduction in patients with schizophrenia during resting condition
Authors: Rutter Lindsay , Carver Frederick W. , Holroyd Tom , Nadar Sreenivasan Rajamoni , Mitchell‐Francis Judy , Apud Jose , Weinberger Daniel R. , Coppola Richard
Published: March 2009

Objective:The “default network” represents a baseline condition of brain function and is of interest in schizophrenia research because its component brain regions are believed to be aberrant in the disorder. We hypothesized that magnetoencephalographic (MEG) source localization analysis would reveal abnormal resting activity within particular frequency bands in schizophrenia.Experimental Design:Eyes‐closed resting state MEG signals were collected for two comparison groups. Patients with schizophrenia (N= 38) were age‐gender matched with healthy control subjects (N= 38), and with a group of unmedicated unaffected siblings of patients with schizophrenia (N= 38). To localize 3D‐brain regional differences, synthetic aperture magnetometry was calculated across established frequency bands as follows: delta (0.9–4 Hz), theta (4–8 Hz), alpha (8–14 Hz), beta (14–30 Hz), gamma (30–80 Hz), and super‐gamma (80–150 Hz).Principle Observations:Patients with schizophrenia showed significantly reduced activation in the gamma frequency band in the posterior region of the medial parietal cortex. As a group, unaffected siblings of schizophrenia patients also showed significantly reduced activation in the gamma bandwidth across similar brain regions. Moreover, using the significant region for the patients and examining the gamma band power gave an odds ratio of 6:1 for reductions of two standard deviations from the mean. This suggests that the measure might be the basis of an intermediate phenotype.Conclusions:MEG resting state analysis adds to the evidence that schizophrenic patients experience this condition very differently than healthy controls. Whether this baseline difference relates to network abnormalities remains to be seen. Hum Brain Mapp, 2009. © 2009 Wiley‐Liss, Inc.
Accreditation systems in Japan and the United States: A comparative perspective on governmental involvement
Authors: Mori Rie
Published: March 2009

An external perspective suggests points of convergence and difference between the U.S. and Japanese approaches to quality assurance in higher education.
Genetic polymorphisms of estrogen metabolizing enzyme and breast cancer risk in Thai women
Authors: Sangrajrang Suleeporn , Sato Yasunori , Sakamoto Hiromi , Ohnami Sumiko , Laird Nan M. , Khuhaprema Thiravud , Brennan Paul , Boffetta Paolo , Yoshida Teruhiko
Published: March 2009

Estrogen and its metabolites are believed to play important roles in breast cancer, and its determinants include both genetic and lifestyle factors. The objective of the study is to investigate the association of breast cancer risk in Thailand with genetic polymorphisms in several genes involved in estrogen synthesis and metabolism. Five hundred and seventy patients with histopathologically confirmed breast cancer and 497 controls were included in the present study. Forty single nucleotide polymorphisms (SNPs) in the CYP1A1, CYP1A2, CYP1B1, CYP17, CYP19, CYP2C9, CYP2C19, AhR, ESR1, PGR, ERRG, COMT, HSD17B1, HSD17B2, EPHX1 and NQO1 genes were genotyped. Association of genotypes with breast cancer risk was evaluated using multivariate logistic regression, which suggested an altered risk for the following SNPs [gene, odds ratio (OR) and 95% confidence interval are shown]: heterozygote carriers of rs4917623 [CYP2C19, OR = 1.38 (1.04–1.84)], rs2066853 [AhR, OR = 1.34 (1.02–1.76)] and rs1857407 [ERRG, (OR = 0.72 (0.55–0.96)]; homozygote carriers of rs762551 [CYP1A2, OR = 2.75 (1.47–5.14)], rs4917623 [CYP2C19, OR = 1.48 (1.00–2.19) and rs945453 [ERRG, OR = 1.66 (1.04–2.65)]. In addition, a stratified analysis by menopausal status indicated that the association of the CYP1A2 (rs762551) and CYP17 (rs743572) polymorphisms with breast cancer risk were mainly evident in premenopausal, while ERRG (rs1857407) was significant in postmenopausal women. These findings suggest that CYP1A2, CYP2C19, AhR, ERRG and CYP17 polymorphisms may play an important role in estrogen metabolism and modify individual susceptibility to breast cancer in Thai women. © 2009 UICC
Caregivers' disrupted representations of the unborn child predict later infant–caregiver disorganized attachment and disrupted interactions
Authors: Crawford Allison , Benoit Diane
Published: March 2009

Infant disorganized attachment is a significant predictor for later psychopathology. The Working Model of the Child Interview (WMCI; C.H. Zeanah, D. Benoit, & M.L. Barton, 1986) elicits and classifies caregivers' perceptions and subjective experience of their child and relationship with the child, which are related to concurrent and future attachment to the caregiver. However, when the WMCI was first developed, the disorganized attachment classification had not been fully developed, so the original WMCI did not include a classification that is linked to disorganized attachment. We adapted the WMCI coding scheme to include items similar to those identified by K. Lyons‐Ruth, E. Bronfman, and E. Parsons (using the Atypical Maternal Behavior Instrument for Assessment and Classification, or AMBIANCE, 1999), which reflect disrupted caregiver behaviors associated with disorganized attachment. This resulted in a new WMCI‐Disrupted (WMCI‐D) scale and classification, disrupted. WMCI‐D was used to code 35 WMCIs administered prenatally. A prenatal disrupted classification was significantly associated with caregiver unresolved classification on the Adult Attachment Interview (M. Main, N. Kaplan, & J. Cassidy, 1985), infant disorganized Strange Situation classification (M.D.S. Ainsworth, M.C. Blehar, E. Waters, & S. Wall, 1978), and disrupted caregiver behaviors toward the infant (using AMBIANCE; K. Lyons‐Ruth et al., 1999), at infant age 12 months. These data suggest WMCI‐D can capture disrupted caregiver internal representations, and identify dyads at risk for disorganized attachment and caregivers with unresolved mourning/trauma. These data also provide evidence for the convergent and predictive validity of the WMCI‐D Scale.
Effectively involving faculty in the assessment of student engagement
Authors: Laird Thomas F. Nelson , Smallwood Robert , Niskodé‐Dossett Amanda Suniti , Garver Amy K.
Published: March 2009

This chapter discusses four roles—source of data, audience, data analyst, and beneficiary of assessment knowledge—faculty can play in the assessment of student engagement on college and university campuses.
Cyclopamine‐induced synophthalmia in sheep: defining a critical window and toxicokinetic evaluation
Authors: Welch K. D. , Panter K. E. , Lee S. T. , Gardner D. R. , Stegelmeier B. L. , Cook D.
Published: March 2009

Cyclopamine, a steroidal alkaloid, from the plant Veratrum californicum is teratogenic, causing a range of different birth defects. The critical window for cyclopamine‐induced synophthalmia formation has been reported to be gestational day (GD) 14. The objectives of this study were to better describe cyclopamine‐induced craniofacial deformities, to better define the window of susceptibility to synophthalmia formation, and to characterize cyclopamine toxicokinetics in sheep. Ewes were dosed i.v. with purified cyclopamine for toxicokinetic analysis. Another four groups of ewes were dosed orally twice daily with 0.88 g/kg of V. californicum on GD 13, 14 or 15 or consecutively on GD days 13–15. Pregnancy and pre‐partum fetal malformations were determined by ultrasound imaging on GD 60. At parturition lambs were assessed for gross malformations. The elimination half‐life of cyclopamine in ewes was determined to be 1.1 ± 0.1 h. The rapid clearance of cyclopamine indicates that ingestion of V. californicum must occur during a very narrow window for synophthalmia formation to occur. Ewes dosed with V. californicum on GD 13 or 14 had lambs with various craniofacial malformations including cyclopia, maxillary dysplasia and mandibular micrognathia. Ewes dosed on GD 15 delivered normal lambs. Ewes dosed consecutively on GD 13–15 were not pregnant at GD 60 and Veratrum‐induced embryonic death was assumed to be the cause. Interestingly, lambs with cyclopia were smaller, under‐developed and appeared premature even though their twin appeared fully developed. Initial evaluations suggest this was due to placental dysplasia. Published in 2009 by John Wiley & Sons, Ltd.
Functionally graded β‐TCP/PCL nanocomposite scaffolds: In vitro evaluation with human fetal osteoblast cells for bone tissue engineering
Authors: Ozkan Seher , Kalyon Dilhan M. , Yu Xiaojun
Published: March 2009

The engineering of biomimetic tissue relies on the ability to develop biodegradable scaffolds with functionally graded physical and chemical properties. In this study, a twin‐screw‐extrusion/spiral winding (TSESW) process was developed to enable the radial grading of porous scaffolds (discrete and continuous gradations) that were composed of polycaprolactone (PCL), β‐tricalciumphosphate (β‐TCP) nanoparticles, and salt porogens. Scaffolds with interconnected porosity, exhibiting myriad radial porosity, pore‐size distributions, and β‐TCP nanoparticle concentration could be obtained. The results of the characterization of their compressive properties and in vitro cell proliferation studies using human fetal osteoblast cells suggest the promising nature of such scaffolds. The significant degree of freedom offered by the TSESW process should be an additional enabler in the quest toward the mimicry of the complex elegance of the native tissues. © 2009 Wiley Periodicals, Inc. J Biomed Mater Res, 2010
Fibronectin‐DNA‐apatite composite layer for highly efficient and area‐specific gene transfer
Authors: Oyane Ayako , Murayama Masami , Yamazaki Atsushi , Sogo Yu , Ito Atsuo , Tsurushima Hideo
Published: March 2009

In 2004, Shen et al. developed a safe and efficient gene transfer system using a DNA‐apatite composite layer. We have recently succeeded in improving further the gene transfer efficiency by immobilizing a cell adhesion molecule laminin, in a DNA‐apatite composite layer. In this study, we showed that not only laminin but fibronectin immobilized in a DNA‐apatite composite layer enhances cell adhesion and cell spreading on the layer, thereby markedly improving the gene transfer efficiency. Therefore, the immobilization of a cell adhesion molecule in a DNA‐apatite composite layer is crucial for improving the gene transfer efficiency. By using fibronectin instead of laminin and optimizing the condition to prepare the fibronectin‐DNA‐apatite composite layer, the amount (weight) of cell adhesion molecule required was reduced to approximately one‐fourth while retaining the relatively high gene transfer efficiency. It was also shown that the resulting fibronectin‐DNA‐apatite composite layer prepared under the optimized condition mediated the area‐specific gene transfer on its surface, that is, DNA was preferentially transferred to the cells adhering to the surface of the fibronectin‐DNA‐apatite composite layer. The present gene transfer system with potential for area‐specific transfection and advantages of safety and relatively high efficiency would be useful in tissue engineering applications, gene therapy, and production of transfection microarrays. © 2009 Wiley Periodicals, Inc. J Biomed Mater Res, 2010
MUC4 involvement in ErbB2/ErbB3 phosphorylation and signaling in response to airway cell mechanical injury
Authors: Theodoropoulos George , Carraway Coralie A. Carothers , Carraway Kermit L.
Published: March 2009

The receptor tyrosine kinases ErbB2 and ErbB3 are phosphorylated in response to injury of the airway epithelium. Since we have shown that the membrane mucin MUC4 can act as a ligand/modulator for ErbB2, affecting its localization in polarized epithelial cells and its phosphorylation, we questioned whether Muc4 was involved, along with ErbB2 and ErbB3, in the damage response of airway epithelia. To test this hypothesis, we first examined the localization of MUC4 in human airway samples. Both immunocytochemistry and immunofluorescence showed a co‐localization of MUC4 and ErbB2 at the airway luminal surface. Sequential immunoprecipitation and immunoblotting from airway cells demonstrated that the MUC4 and ErbB2 are present as a complex in airway epithelial cells. To assess the participation of MUC4 in the damage response, cultures of NCI‐H292 or airway cells were scratch‐wounded, then analyzed for association of phospho‐ErbB2 and ‐ErbB3 with MUC4 by sequential immunoprecipitation and immunoblotting. Wounded cultures exhibited increased phosphorylation of both receptors in complex with MUC4. Scratch wounding also increased activation of the downstream pathway through Akt, as predicted from our previous studies on Muc4 effects on ErbB2 and ErbB3. The participation of MUC4 in the phosphorylation response was also indicated by siRNA repression of MUC4 expression, which resulted in diminution of the phosphorylation of ErbB2 and ErbB3. These studies provide a new model for the airway epithelial damage response, in which the MUC4–ErbB2 complex is a key element in the sensor mechanism and phosphorylation of the receptors. J. Cell. Biochem. 107: 112–122, 2009. © 2009 Wiley‐Liss, Inc.
Inorganic phosphate modulates responsiveness to 24,25(OH)2D3 in chondrogenic ATDC5 cells
Authors: Denison Tracy A. , Koch Christopher F. , Shapiro Irving M. , Schwartz Zvi , Boyan Barbara D.
Published: March 2009

Chondrogenic ATDC5 cells were used as a model of in vitro endochondral maturation to study the role of inorganic phosphate (Pi) in the regulation of growth plate chondrocytes by vitamin D3 metabolites. ATDC5 cells that were cultured for 10 days post‐confluence in differentiation media and then treated for 24 h with Pi produced a type II collagen matrix based on immunohistochemistry and expressed mRNAs for several chondrocytic markers, including aggrecan, collagen types II and X, cartilage oligomeric matrix protein, and SOX9. Pi also caused a decrease in [35S]‐sulfate incorporation and stimulated apoptosis, as evidenced by increased DNA fragmentation and caspase‐3 activity. In addition, treatment with Pi induced sensitivity to 24,25‐dihydroxyvitamin D3 and this effect was both dose‐dependent and was blocked by phosphonoformic acid (PFA), a specific inhibitor of sodium dependent type III Pi transporters. Treatment with 24R,25(OH)2D3 reduced cell number and increased alkaline phosphatase specific activity in a dose‐dependent manner. Moreover, 24R,25(OH)2D3 reversed the Pi‐induced decrease in incorporation of [3H]‐thymidine and [35S]‐sulfate incorporation, as well as the Pi‐induced increase in apoptosis. These results suggest that Pi acts as an early chondrogenic differentiation factor, inducing response to 24R,25(OH)2D3; treatment of committed chondrocytes with Pi induces apoptosis, but 24R,25(OH)2D3 mitigates these effects, indicating a possible inhibitory feedback loop. J. Cell. Biochem. 107: 155–162, 2009. © 2009 Wiley‐Liss, Inc.
Serum lipid profile, oxidative status, and paraoxonase 1 activity in hyperemesis gravidarum
Authors: Aksoy Hulya , Aksoy Ayse Nur , Ozkan Asuman , Polat Harun
Published: March 2009

The aim of this study was to investigate lipid profile, paraoxonase 1 (PON1) activity, and oxidative stress status in the serum of hyperemesis gravidarum (HG) patients. Thirty‐six HG cases and 36 normal pregnants were included in the study. Serum total cholesterol (TC), triglyceride (TG), high‐density lipoprotein cholesterol (HDL‐C), low‐density lipoprotein cholesterol (LDL‐C), apoproteins A1 (apo A1) and B (apo B), malondialdehyde (MDA), and total antioxidant activity (TAO) values and PON1 and arylesterase activities were determined. Although serum TC, TG, LDL‐C, and apo B levels were not different among; the groups (P>0.05), HDL‐C (P=0.01) and apo A1 (P=0.007) levels were lower in HG patients than in normal pregnants. HG group had significantly lower serum PON1 (P=0.03) and arylesterase activities (P=0.03) compared with the control group. Additionally, mean TAO values were lower (P=0.01) and MDA levels were higher (P=0.02) in HG group than in the healthy pregnants. A significant negative correlation between PON1 and MDA was found in HG group (r=−0.33, P<0.05). The findings of this study have revealed that HG may be one of the conditions in which oxidant and antioxidant balance is impaired. J. Clin. Lab. Anal. 23:105–109, 2009. © 2009 Wiley‐Liss, Inc.
Cell death induced by zinc and cadmium is mediated by clusterin in cultured mouse seminiferous tubules
Authors: Kaisman‐Elbaz Tehila , Sekler Israel , Fishman Daniel , Karol Nataly , Forberg Michal , Kahn Nicole , Hershfinkel Michal , Silverman William F.
Published: March 2009

Sertoli cells, lining the walls of the seminiferous tubules, are in close contact with and regulate all aspects of the development of the germ cells. Clusterin, is a glycoprotein produced abundantly by Sertoli cells, and associated with either apoptosis or cell survival. Zinc is present in high concentrations in the testis and required for sperm development by an as yet unknown mechanism. Permeation of zinc into cells via voltage‐gated calcium channels (VGCCs), however, is suggested to induce cell death. We examined the possibility that Zn2+ acts via clusterin to regulate germ cell survival. Employing an ex vivo model of mouse testis, we have assessed the role of permeation of heavy metal ions on clusterin production and secretion. Up‐regulation of clusterin expression and its secretion was observed after a short exposure to zinc or to cadmium under depolarizing conditions. Expression of zinc transporter‐1 (ZnT‐1), previously shown to regulate Zn2+ influx, increased following prolonged application of zinc or cadmium to the explants and prevented clusterin up‐regulation by subsequent exposure to these ions. Inhibition of the MAPK and PI3K pathways reduced the up‐regulation of clusterin following the intracellular rise of Zn2+ or Cd2+. Neutralization of secreted clusterin by an antibody or attenuation of clusterin up‐regulation by inhibition of Zn2+ permeation via the LTCC, reduced cell death in cultured seminiferous tubule cells. Taken together, our results indicate that Zn2+ and Cd2+ influx induce expression and secretion of clusterin, thereby linking metal homeostasis and germ cell fate. J. Cell. Physiol. 220: 222–229, 2009. © 2009 Wiley‐Liss, Inc.
FGF2 stimulates SDF‐1 expression through the Erm transcription factor in Sertoli cells
Authors: Yoon Kyung‐Ae , Chae Young‐Mi , Cho Je‐Yoel
Published: March 2009

Ets‐related molecule (Erm) is a member of the Ets transcription factor family. Erm is known to be an important factor for the self‐renewal of Spermatogonial stem cells (SSCs) and the maintenance of spermatogenesis. We investigated the molecular mechanism of Erm regulation on SDF‐1 in TM4 Sertoli cells. Erm and Sdf‐1 levels were up‐regulated after FGF2 treatment in TM4 cells, whereas these levels were significantly decreased by FGF2 in ST2 bone marrow stromal cells. Knockdown of Erm by siRNA in the presence of FGF2 decreased the Sdf‐1 levels in TM4 cells. The expression levels of Erm were similar and Erm overexpression increased the Sdf‐1 in both TM4 and ST2 cells. FGFR subtype analysis revealed that FGFR4 was expressed in TM4 cells but not in ST2 cells. A blocking experiment also confirmed that FGFR4 is partly responsible for the up‐regulation of Erm and SDF‐1 induced by FGF2 stimulation in TM4 cells. FGF2 and ERM increased the activity of Sdf‐1 gene promoter region in a dose‐dependent manner. EMSA revealed that ERM strongly binds to the −846 to −851 nucleotide region of the potential Ets binding site (EBS) in the Sdf‐1 promoter. In addition, CXCR4, the SDF‐1 receptor, was expressed in spermatogonia and Sertoli cells in the seminiferous tubules of the mouse testis. Our results indicate that ERM directly regulates Sdf‐1 gene expression by interacting with its cis‐acting element in response to FGF2 stimulation in TM4 cells. J. Cell. Physiol. 220: 245–256, 2009. © 2009 Wiley‐Liss, Inc.
Removal of selected pharmaceuticals in waters by photochemical processes
Authors: Benitez F Javier , Real Francisco J , Acero Juan L , Roldan Gloria
Published: March 2009

BACKGROUND: Large amounts of pharmaceutical compounds are consumed throughout the world, and after being metabolized in humans are discharged into water streams. Some of them are not completely removed in wastewater treatment plants and, as a result, they are found in some effluents as well as in surface and ground waters.

RESULTS: Four pharmaceutical compounds (metoprolol, naproxen, amoxicillin and phenacetin) frequently found in wastewaters were selected to be individually photo‐oxidized in ultra‐pure water by monochromatic UV radiation. The influence of independent variables (pH, temperature, and additional presence of hydrogen peroxide) was established, and first‐order rate constants and quantum yields evaluated. The compounds were also oxidized using Fenton's reagent and, after establishing the influence of the operating conditions (ferrous ions and hydrogen peroxide concentrations, pH and additional presence of UV radiation), the rate constants for the radical reaction between each pharmaceutical and hydroxyl radicals were determined. Finally, the simultaneous photo‐oxidation of mixtures of the selected pharmaceuticals in several types of water (commercial mineral water, groundwater and reservoir water) was performed by means of UV radiation alone and by the combination UV/H2O2. The influence of the independent variables in these processes was discussed, and the kinetic study allowed the determination of various rate constants for each compound.

CONCLUSION: As the pharmaceutical concentrations theoretically calculated by the proposed kinetic model agree well with the experimental results obtained, this model constitutes an excellent tool to predict the elimination of these compounds when they are present in different natural waters. Copyright © 2009 Society of Chemical Industry
Circular choosability
Authors: Havet Frédéric , Kang Ross J. , Müller Tobias , Sereni Jean‐Sébastien
Published: March 2009

We study circular choosability, a notion recently introduced by Mohar and Zhu. First, we provide a negative answer to a question of Zhu about circular cliques. We next prove that cch(G)=O(ch(G)+ln|V(G)|) for every graph G. We investigate a generalization of circular choosability, the circular f‐choosability, where f is a function of the degrees. We also consider the circular choice number of planar graphs. Mohar asked for the value of τ ≔ sup{cch(G) : G is planar}, and we prove that 6≤τ≤8, thereby providing a negative answer to another question of Mohar. We also study the circular choice number of planar and outerplanar graphs with prescribed girth, and graphs with bounded density. © 2009 Wiley Periodicals, Inc. J Graph Theory 61: 241–270, 2009
Chemistry of pyrones related to dehydroacetic acid. Functionalization at C‐5 and at the methyl group at C‐6. An attempted synthesis of a thromboxane B2 analogue
Authors: Bacardit R. , Cervelló J. , de March P. , Marquet J. , Moreno‐Mañas M. , Roca J. L.
Published: March 2009

New derivatives of dehydroacetic acid and triacetic acid lactone functionalized at both C‐5 and at the methyl group at C‐6 have been synthesized as intermediates for the preparation of thromboxane B2 analogues. 6‐Mercaptomethyl‐4‐methoxy‐2‐pyrone and some derived thioethers have been also prepared. New thioether derivatives of O‐alkyloximes of dehydroacetic acid have been synthesized and tested for herbicidal activity.
Chemistry of condensed thiophenes. III. Acetylation of triphenyleno [1,12‐bcd]thiophene
Authors: Klemm L. H. , Hall Eliot , Lee Wai M. , Tran Long K.
Published: March 2009

Friedel‐Crafts reaction of triphenyleno[1,12‐bcd]thiophene (2) by means of aluminum chloride, nitrobenzene, and a limited excess of acetyl chloride yielded 3‐acetyl‐2 (78%) and 3,5‐diacetyl‐2 (7%). Use of a large excess of acetyl chloride gave yields of 42% and 22%, respectively. Wolff‐Kishner reduction of the acetyl compounds produced 3‐ethyl‐2 (15%) and 3,5‐diethyl‐2 (8%). Structures were assigned largely on the basis of 1H nmr and ultraviolet absorption spectra of the products.
Synthesis of 3‐substituted‐2‐benzothiazolinone, 2‐benzoxazolinone and benzothiazoline‐2‐thione
Authors: D'Amico John J. , Bollinger Frederic G.
Published: March 2009

The reaction of 2‐benzothiazolinone, 2‐benzoxazolinone or benzothiazoline‐2‐thione under basic conditions with various electrophiles afforded the titled compounds 1‐13, 29‐31 and 40‐48. The 3‐(substituted‐aminomethyl)‐2‐benzothiazolinone and related compounds 14‐25 were prepared by the reaction of 3‐(hydroxymethyl)‐2‐benzothiazolinone or the appropriate 2‐benzothiazolinone and formaldehyde with the appropriate amine or substituted aniline. The reaction of 9, 13 or 25 with methyl iodide afforded the quaternary ammonium iodides 26‐28. The reaction of the appropriate potassium salts of various phenol with 3‐(chloromethyl)‐2‐benzothiazolinone afforded the 3‐(substituted‐phenoxymethyl)‐2‐benzothiazolinone and related compounds 32‐39. The ethyl or isopropylxanthates 49‐54 were synthesized by the reaction of 3‐(chloromethyl)‐2‐benzo‐thiazolinone and appropriate compounds with potassium ethyl or isopropyl xanthate. The reaction of 3‐(chloromethyl)‐2‐benzothiazolinone with sodium sulfide afforded the sulfide 55.
Carba‐acyclonucleoside antiherpetic agents
Authors: Hannah John , Tolman Richard L. , Karkas John D. , Liou Richard , Perry Helen C. , Field A. Kirk
Published: March 2009

Ganciclovir 2 and 2′‐carba‐ganciclovir 5a are anti‐viral agents differing structurally only in the replacement of an oxygen by a methylene group and yet expressing their biological properties along mechanistically independent pathways. Methoxy, hydroxy and fluoro derivatives of 2′‐carba‐ganciclovir were prepared to examine the effect of re‐introducing a binding site close to that in the original oxa side chain. The cyclic phosphate of carba‐ganciclovir was also prepared.
Methyl 2‐benzoylamino‐3‐dimethylaminopropenoate in the synthesis of heterocyclic systems. The synthesis of benzoyl‐ amino substituted 7H‐pyrano[2,3‐d]pyrimidine, 1H,6H‐pyrano‐ [2,3‐c]pyrazole and 2H‐1‐benzopyran derivatives
Authors: Stanovnik Branko , Svete Jurij , Tišler Miha
Published: March 2009

Methyl 2‐benzoylamino‐3‐dimethylaminopropenoate (6) reacts with heterocyclic compounds containing an active methylene group or potential methylene group in the ring system, such as barbituric acid derivatives 1 and 2, pyrazolones 3 and 4, and resorcinol, in acetic acid to afford the corresponding benzoylamino substituted pyranopyrimidinones 7 and 8, pyranopyrazolones 9 and 10, and 2H‐1‐benzopyranone 11. The method represents a novel procedure for the preparation of condensed pyranones.
Nitroimidazoles. VI. Syntheses of 1‐methyl‐2‐(1,3,4‐thiadiazol‐2‐yl)‐5‐nitroimidazole and 1‐methyl‐2‐(1,3,4‐oxadiazol‐2‐yl)‐5‐nitroimidazole
Authors: Shafiee A. , Yazdikarimy B. , Sadrai S.
Published: March 2009

Starting from readily available 1‐methyl‐5‐nitroimidazole‐2‐carboxylic acid hydrazide (1), 1‐methyl‐2‐(1,3,4‐thiadiazol‐2‐yl)‐5‐nitroimidazole (4) and 1‐methyl‐2‐(1,3,4‐oxadiazol‐2‐yl)‐5‐nitroimidazole (10) were prepared. The reaction of 1 with formic acid gave 1‐(1‐methyl‐5‐nitroimidazole‐2‐carboxyl)‐2‐(formyl)hydrazine (8) in high yield. Refluxing of the latter with phosphorus pentasulfide in xylene yielded compound 4 in 50% yield. Reaction of compound 8 with phosphorus pentoxide afforded compound 10 in 60% yield.
Studies in spiroheterocycles, Part XV. Investigation of the reaction of 3‐(2‐oxocycloalkylidene)‐indol‐2‐ones with thiourea and urea derivatives
Authors: Joshi Krishna C. , Dandia Anshu , Sanan Sangeeta
Published: March 2009

The reaction of 3‐(2‐oxocycloalkylidene)indol‐2‐one 1 with thiourea and urea derivatives has been investigated. Reaction of 1 with thiourea and urea in ethanolic potassium hydroxide media leads to the formation of spiro‐2‐indolinones 2a‐f in 40–50% yield and a novel tetracyclic ring system 4,5‐cycloalkyl‐1,3‐diazepino‐[4,5‐b]indole‐2‐thione/one 3a‐f in 30–35% yield. 3‐(2‐Oxocyclopentylidene)indol‐2‐one afforded 5′,6′‐cyclopenta‐2′‐thioxo/ oxospiro[3H‐indole‐3,4′(3′H)pyrimidin]‐2(1H)‐ones 2a,b and 3‐(2‐oxocyclohexylidene)indol‐2‐one gave 2′,4′a,5′,6′,7′,8′‐ hexahydro‐2′‐thioxo/oxospiro[3H‐indole‐3,4′ (3′H)‐quinazolin]‐2(1H)‐ones 2c‐f. Under exactly similar conditions, reaction of 1 with fluorinated phenylthiourea/cyclohexylthiourea/phenylurea gave exclusively spiro products 2g‐1 in 60–75% yield. The products have been characterized by elemental analyses, ir pmr. 19F nmr and mass spectral studies.
A regiocontrolled synthesis of substituted indoles by palladium‐catalyzed coupling of 2‐bromonitrobenzenes and 2‐bromoacetanilides
Authors: Kasahara Akira , Izumi Taeko , Murakami Satoshi , Miyamoto Kazuhiro , Hino Toshimi
Published: March 2009

The palladium‐catalyzed cross‐coupling reaction of 2‐bromonitrobenzenes or 2‐bromoacetanilides with ethylene has been used to produce a variety of substituted indoles. The mild reaction conditions and selectivity inherent in the coupling reaction have been utilized to produce regiochemically pure 4‐, 5‐, 6‐, and 7‐substituted indoles.
Rearrangement of 1,3‐thiazolidine sulfoxides
Authors: Mah He Duck , Lee Wha Suk
Published: March 2009

Oxidation of 1,3‐thiazolidines 3 gave a mixture of cis‐ and trans‐sulfoxides 4 and 5, major and minor, respectively. In the presence of an acid catalyst both the cis and trans sulfoxides underwent ring expansion reaction to produce dihydro‐1,4‐thiazines 2 in good yields. Under neutral conditions (100°/DMF) the cis‐sulfoxides afforded a sigmatropic rearrangement with the 2‐methylene group to generate probable sulfenic acids 6 followed by dehydration to 2, while the trans isomer rearranged more slowly involving the 2‐methyl group to form isomeric dihydrothiazines 18 possibly via sulfenic acids 7. Structures and isomerization of the cis‐ and trans‐sulfoxides are also discussed.
Régiospécificité de la cycloaddition des diarylnitrilimines sur quelques dérivés indoliques
Authors: Daou Boujemaâ , Soufiaoui Mohamed , Carrié Robert
Published: March 2009

Ce mémoire décrit les résultats de l'étude de la réaction de diarylnitrilimines (DANI) sur le N‐éthylindole (1) et sur le méthoxycarbonyl‐2 N‐éthylindole (2). Suivant la nature du dipolarophile (1 ou 2) la régiospécificité de la réaction s'inverse. Cette dernière est établie par voie spectroscopique et chimique.
Acetylenic chemistry: Part 13. Synthesis of oxazoles and oxazoloquinazolines from o‐amino‐N‐(1,1 ‐disubstituted‐propynyl)benzamide
Authors: Reisch J. , Usifoh C. O. , Oluwadiya J. O.
Published: March 2009

Conversion of isatoic anhydride to o‐amino‐N(1,1‐disubstituted‐propynyl)benzamides 3a‐c followed by reflux in ethanolic potassium hydroxide gave 2‐(o‐aminophenyl)‐4,4‐disubstituted‐5‐methylene‐4H‐oxazoles 4a‐c. The treatment of same 3a‐c with triphosgene in pyridine with subsequent reflux gave 4a‐c and 2‐methylene‐3,3‐disubstituted‐oxazolo[2,3‐b]quinazolin‐5(3H)‐ones 5a‐c.
The synthesis of novel crown ethers, part ix, 3‐phenyl chromenone‐crown ethers
Authors: Bulut M. , Erk Ç L.
Published: March 2009

3‐Phenyl‐ and 3‐(p‐methoxyphenyl)‐7,8‐dihydroxy and ‐6,7‐dihydroxychromenones were prepared from ethyl 3‐oxo‐2‐phenylpropanoate, ethyl 3‐oxo‐2‐(4‐methoxyphenyl)‐propanoate and the trihydroxy benzenes in H2SO4. 3‐Aryl‐7,8‐ and 3‐aryl‐6,7‐dihydroxy‐2H‐chromenones reacted with the bis‐dihalides of poly‐glycols in DMF/MeCO3 to afford 12‐Crown‐4, 15‐Crown‐4 and 18‐Crown‐6‐chromenones. The products were identified with IR, 1H NMR, low and high resolution mass spectroscopy and elemental analysis. Some 1:1 cation association constants, Kb, of the 3‐phenyl chromenone crown ethers with Li+, Na+, K+ and Rb+ cations were studied by steady state emission fluorescence spectroscopy; Kb chromenone‐crown complexes displayed crown ether‐cation binding selectivity rules properly in acetonitrile.
Complexing properties of 3′,5′‐disubstituted‐4′‐hydroxybenzyl armed monoaza‐12‐crown‐4 and armed monoaza‐15‐crown‐5 ethers and crystal structures of the alkali metal ion complexes
Authors: Habata Yoichi , Akabori Sadatoshi , Zhang Xian Xin , Izatt Reed M. , Bradshaw Jerald S.
Published: March 2009

A series of monoaza‐15‐crown‐5 ethers (2b‐2h) having 4′‐hydroxy‐3′,5′‐disubstituted benzyl groups have been prepared by the Mannich reaction of 2,6‐disubstituted phenols with the corresponding N‐methoxymethylmonoaza‐crown ethers. Competitive transport through a chloroform membrane by 12‐crown‐4 derivatives (lithium, potassium and cesium) and 15‐crown‐5 derivatives (sodium, potassium and cesium) were measured under basic‐source phase and acidic‐receiving phase conditions. All ligands transported size‐matched alkali‐metal cations. Ligands 1h and 2h with two fluorine atoms in the side arm gave higher metal ion transport rates than those of dimethyl‐ (1a and 2a), diisopropyl‐ (1b and 2b), and butylmethyl‐ (1d and 2d) derivatives. X‐ray crystal structures of six alkali metal complexes with monoaza‐12‐crown‐4‐derivatives (1b‐LiSCN, 1b‐KSCN, 1c‐NaSCN, 1d‐LiSCN, 1f‐RbSCN and 1h‐LiSCN) and three alkali metal complexes with 15‐crown‐5 derivatives (2b‐KSCN, 2c‐KSCN, and 2e‐KSCN) along with crystal structures of some new ligands (1b, 1c, 1d, 1f, and 2c) are also reported. These X‐ray analyses indicate that the crystal structures of the alkali metal ion complexes of these new armed‐crown ethers changed depending on the substituents at the 3′‐ and 5′‐positions of the appended hydroxybenzyl arms.
Synthesis of macrocyclic bis(phenylbenzoxazole) derivatives via tandem claisen rearrangement and their fluorescence behavior
Authors: Koyama Emiko , Tokuhisa Hideo , Nagawa Yoshinobu , Yang Gang , Hiratani Kazuhisa
Published: March 2009

Novel macrocyclic bis(phenylbenzoxazole) derivatives were easily synthesized from macrocyclic isobutenyl bis(amide‐ether)s by tandem Claisen rearrangement and subsequent intramolecular cyclization of the amide‐phenol intermediates. The position of substitution of the oligoethylene glycol moiety on the phenylamido groups of the macrocycles did not have a large effect on the yields of the bis(benzoxazole)s for the meta and para derivatives. The fluorescence quantum yields of most of the macrocyclic bis(benzoxa‐zole)s were lower than those of the corresponding nonmacrocyclic bis(benzoxazole) model compounds. The quantum yields of the para‐substituted macrocyclic bis(benzoxazole)s were clearly lower than those of the model compounds and decreased with increasing length of the oligoethylene chain.
A supramolecular assembly containing an unusually short n‐h…n hydrogen bond ‐ an x‐ray and neutron diffraction study
Authors: Bishop Michael M. , Lindoy Leonard F. , Bishop Michael M. , Thorn‐Seshold Oliver T. , Piltz Ross O. , Turner Peter
Published: March 2009

A supramolecular assembly formed between phthalimide and 2‐guanidinobenzimidazole, containing a short 2.692(4)AR N‐H…N hydrogen bond, is reported. The crystal structure of this species was determined by both X‐ray and neutron diffraction. The diffraction data reveal that the proton involved in the short hydrogen bond has been transferred from the phthalimide to the guanidinobenzimidazole to form an ion pair. There is also an interesting stacking interaction between the atoms involved in the short hydrogen bond and the π system of a phthalimide molecule that is approximately 3.3 Å away. The structure is compared with the structure of a similar assembly formed between 4‐nitrophthalimide and 2‐guanidinobenzimidazole.
New C(2)‐substituted 8‐alkylsulfanyl‐9‐phenylmethyl‐hypoxanthines III
Authors: Biagi Giuliana , Giorgi Irene , Livi Oreste , Pacchini Federica , Scartoni Valerio , Salerni Oreste Leroy
Published: March 2009

Title compounds were obtained starting from the key imidazole intermediate, 5‐amino‐1‐phenyl‐methyl‐2‐mercapto‐1H‐imidazole‐4‐carboxylic acid amide 5, readily derived from the base catalyzed rearrangement of a thiazole, 5‐amino‐2‐phenylmethylaminothiazole‐4‐carboxylic acid amide 4. Alkylation of the thiol function on 5 with phenylmethyl and allylic chlorides gave compounds 6 and 7 respectively. Cyclization of 6 with a variety of esters afforded 8‐phenylmethylthiohypoxanthines, 8–11. Similarly, 7 was cyclized to 8‐allylthiohypoxanthines, 20–21. Compound 5 was also cyclized, but formed 8‐mercaptohypox‐anthines, 22–24. Alkylation of 8‐mercaptohypoxanthines afforded 8‐alkylthiohypoxanthines, 8, 9,25 and 26 (see Scheme 2). Chlorination of 9–11 afforded 16–18; adenine 19 was derived from 16. Oxidation of hypox‐anthines 8–11 with m‐chloroperbenzoic acid gave the corresponding 8‐phenylmethylsulfonyl derivatives 12‐15. These derivatives proved resistant to nucleophilic displacement reactions with primary amines.
Synthesis of new hetero[1,2,4]thiadiazin‐3‐one S,S‐dioxides and oxazolo[3,2‐b]hetero[1,2,4]thiadiazine S,S‐dioxides as potential psychotropic drugs
Authors: Vega Salvador , Arranz María Esther , Arán Vicente J.
Published: March 2009

A series of 2‐substituted 2H‐thieno[3,4‐e][1,2,4]thiadiazin‐3(4H)‐one 1,1‐dioxides (2), 2‐substituted 2H‐thieno[2,3‐e][1,2,4]thiadiazin‐3(4H)‐one 1,1‐dioxides (3), 2‐substituted 4,6‐dihydropyrazolo[4,3‐e]‐[1,2,4]thiadiazin‐3(2H)‐one 1,1‐dioxides (4), 2‐substituted 2,3‐dihydrooxazolo[3,2‐b]thieno[3,4‐e]‐[1,2,4]thiadiazine 5,5‐dioxides, (5), 6‐substituted 6,7‐dihydro‐2H‐oxazolo[3,2‐b]pyrazolo[4,3‐e][1,2,4]thia‐diazine 9,9‐dioxides (6) and 7‐substituted 6,7‐dihydro‐2H‐oxazolo[3,2‐b]pyrazolo[4,3‐e][1,2,4]thiadiazine 9,9‐dioxides (7) were synthesized as potential psychotropic agents.
Reaction of 2‐acyl‐6‐methylbenzo[b]furan‐3‐acetic acids derivatives with hydrazine
Authors: Tolkunov Valery S. , Perepichka Igor F. , Dulenko Vladimir I.
Published: March 2009

Reaction of 2‐acyl‐6‐methylbenzo[b]furan‐3‐acetic acids and their derivatives such as amides and esters with hydrazine does not give expected 1‐alkyl‐5H‐benzofuro[2,3‐e]diazepin‐4‐ones ones but results in 2‐amino‐7‐methyl‐2H‐benzo[4,5]furo[2,3‐c]pyridin‐3‐ones or (3‐R‐6‐methylbenzo[b]furan‐2‐yl)alkyl ketone azines.
Preparation of dicarboxylate analogues of cerulenin
Authors: Moseley Jonathan D. , Staunton James
Published: March 2009

We have proposed and synthesized several new structural classes of Cerulenin analogues, which have potential as inhibitors of both fatty acid and polyketide synthase multi‐enzyme complexes. These analogues contain cis epoxides bearing flanking carboxylate groups. Our syntheses have been designed to allow access to a wide range of fatty acid and polyketide‐like side chains from readily available starting materials in convergent fashion in just four to five steps. In total, ˜40 potential analogues have been prepared and characterized, covering all the structural sub‐classes proposed, the majority of which constitute novel functional groupings.
Synthesis, structure and electrochemical properties of two new unsymmetrical tetrathiafulvalene derivatives
Authors: Xu Ming , Ji Yong , Zuo Jing‐Lin , Li Yi‐Zhi , You Xiao‐Zeng
Published: March 2009

Two new unsymmetrical tetrathiafulvalene (TTF) derivatives, 2,3‐bis(cyanoethylthio)‐6,7‐(methyl‐ethylenedithio)tetrathiafulvalene (6a) and 2,3‐bis(cyanoethylthio)‐6,7‐(cyclopentodithio)tetrathiafulvalene (6b), have been prepared and characterized by NMR, MS, IR and Elemental analyses. The molecular structures have been determined by X‐ray crystallography. Their redox properties have been investigated by cyclic voltammetry in dichloromethane solution and each compound shows two reversible single‐electron redox couples.
Synthesis of 2H‐chromeno[4,3‐b]pyridine‐2,5(1H)‐diones and related heterocycles via the erlenmeyer‐ploechl reaction
Authors: Ivanov Ivo Christov , Glasnov Toma Nikolaev , Heber Dieter
Published: March 2009

1,2‐Dihydro‐5H‐[1]benzopyrano[4,3‐b]pyridine‐2,5‐diones 4a‐j were synthesized from 4‐alkylamino‐coumarin‐3‐carbaldehydes 1 and 5(4H)‐oxazolinones (azalactones) derived from N‐acetylglycine (2a) and hippuric acid (2b). The intermediates 3 (3j isolated only) underwent spontaneous recyclization via opening of the azalactone and successive formation of the fused 2‐pyridones 4. Attempts to synthesize the selected 2H‐chromeno[3,4‐f]‐1,7‐naphthyridine 6 by Vilsmeier reaction of 4e failed. Instead, N‐deacetylation took place, followed by formylation of the amino group to the formamidine 7a. In addition, pyranopyridine 9a was obtained by condensation of the 3‐formyl‐2‐pyridone 8 with the azalactone derived from 2a and acetic anhydride.
Regiospecific synthesis, structure and electron ionization mass spectra of 1,3‐thiazolidin‐4‐ones containing the acridine skeleton
Authors: Géci Imrich , Imrich Ján , Kristian Pavol , Kivelä Henri , Valtamo Pauliina , Pihlaja Kalevi
Published: March 2009

The synthesis of regioisomeric 3‐alkyl(aryl)‐2‐(acridin‐9′‐yl)imino‐1,3‐thiazolidin‐4‐ones (8b‐i) and 2‐alkyl(aryl)imino‐3‐(acridin‐9′‐yl)‐1,3‐thiazolidin‐4‐ones (11a‐i) was performed by the reaction of 3‐(acridin‐9‐yl)‐1‐alkyl(aryl)thioureas 5a‐i with methyl bromoacetate and bromoacetyl bromide, respectively, via the corresponding isothiourea hydrobromides with excellent regioselectivity. The structure, NMR spectra and mass spectrometric behavior of the resulting compounds are discussed.
Synthesis of benz[e]indolium heptamethine cyanines containing C‐substituents at the central portion of the heptamethine moiety
Authors: Salon Jozef , Ska Ewa Woli , Raszkiewicz Aldona , Patonay Gabor , Strekowski Lucjan
Published: March 2009

An efficient procedure for the synthesis of near‐infrared dyes 5a‐d is described.
Reaction of acridine with pyrazolone derivatives
Authors: Ishihara Yoshimi , Ito Takeyuki , Saito Hiroshi , Takano Jiro
Published: March 2009

A mixture of acridine and a pyrazolone derivative was reacted in the solid state (without solvent). It is proposed that the enol tautomer (the C4‐position) of the pyrazolone derivative attacks the C9‐position of acridine through a nucleophilic reaction resulting in products where the C4‐position of pyrazolone is connected to the C9‐position of acridine. When the reaction of 3‐methyl‐1‐phenyl‐5‐pyrazolone and acridine was carried out at low temperature (25°–50°), the reaction product was obtained even when the majority of the reaction mixture had not melted. The same reaction was also carried out in the presence of an ultrasonic wave at same temperature (25°–50°) and the reaction product was obtained in high yield. Under ultrasonic conditions, the reaction mixture was not melted. However, the interface between 3‐methyl‐1‐phenyl‐5‐pyrazolone and acridine gradually changed from white to black. In this reaction, the dihydroacridine dimer is not obtained.
A simple and convenient method for the synthesis of 1‐dialkylaminocarbothioic acid S‐[(2,3‐epithio)propyl] esters
Authors: Kumar Kiran , Sharma V. L. , Dwivedi A. K.
Published: March 2009

magnified image

A simple and convenient method for the synthesis of 1‐dialkylaminocarbothioic acid S‐[(2,3‐epithio)propyl] ester was developed by the reaction of 1‐dialkylaminocarbodithioic acid‐sodium salt with 1‐chloro‐2,3‐epoxypropane in water‐methanol mixture at room temperature. An intermediate was isolated and characterized, based on which a possible mechanism was proposed.
Synthetic study for two 2H‐chromenic acids, 8‐chlorocannabiorcichromenic acid and mycochromenic acid
Authors: Yamaguchi Seiji , Nedachi Masahiro , Maekawa Mikiko , Murayama Yohei , Miyazawa Masahiro , Hirai Yoshiro
Published: March 2009

magnified image

Two 2H‐chromenes having a fully substituted benzene ring, 8‐chlorocannabiorcichromene (1) and mycochromenic acid (2), were synthesized by a condensation of salicylaldehydes with isopropylidenemalonate or the thermal cyclization of corresponding propargyl ethers.
Synthesis of 5‐substituted 2‐(2,4‐dihydroxyphenyl)‐1,3,4‐thiadiazoles
Authors: Matysiak J.
Published: March 2009

magnified image

One‐stage synthesis of 5‐substituted (alkyl, aryl, heteroaryl, arylalkyl, heteroalkyl, alkoxy‐, aryloxy)‐2‐(2,4‐dihydroxyphenyl)‐1,3,4‐thiadiazoles is described. The compounds were prepared by the reaction of sulfinyl‐bis(2,4‐dihydroxythiobenzoyl) (STB) with hydrazides or carbazates. The structure of new compounds was assigned by ir, nmr and ms data.
Synthesis of novel substituted flavonoids
Authors: Mills Chavonda J. , Mateeva Nelly N. , Redda Kinfe K.
Published: March 2009

magnified image

Eighteen substituted chalcones, flavones and 3‐flavonols were synthesized and characterized using 1H‐NMR, IR and elemental analysis. The substitution pattern includes two halogen atoms, nitro and methyl groups in ring A as well as two or three methoxy groups in ring B.
Regioselective reactions of mesyloxymethylazetidinones with nucleophiles I. Cleavage of the azetidinone ring, azetidinone‐aziridine ring transformations
Authors: Boros Éva , Bertha Ferenc , Fetter József , Czira Gábor , Feller Antal , Simig Gyula , Kajtár‐Peredy Mária
Published: March 2009

magnified image

The reaction of 4‐mesyloxymethylazetidin‐2‐one derivatives 3 with ammonia and sodium methoxide was investigated. The two electrophilic centers of the substrate reactesuccessively, resulting in cleavage of the lactam bond and formation of a new aziridine ring. The resulting type 6 and 8 aziridinylacetic acid derivatives are related to the novel 2‐(aziridin‐2‐yl)‐3‐phenylpropionic acid type carboxypeptidase A inhibitors and, as such, potential drug candidates.
Synthesis of novel halogenated cryptolepine analogues
Authors: Gouni Srinivas Reddy , Carrington S. , Wright C. W.
Published: March 2009

magnified image

Cryptolepine (5‐N‐methyl‐10‐H‐indolo[3,2‐b]quinoline) is an indoloquinoline alkaloid present in the roots of Cryptolepis Sanguinolenta. In its hydrochloride form the alkaloid presents a number of bioactivities. The alkaloid also has cytotoxic properties that are likely to be due to its abilities to intercalate into DNA and inhibit the enzyme topoisomerase II, as well as the synthesis of DNA. In this research project five novel analogues of cryptolepine were chosen for synthesis.