Chemistry Department, Faculty of Science, Mansoura University, El-Gomhoria Street, Mansoura 35516, Egypt.
Eur J Med Chem. 2010 Apr;45(4):1338-45. doi: 10.1016/j.ejmech.2009.12.020. Epub 2009 Dec 21.
2-(5-oxothiazolidinone)-cyanoacetamido derivative 3 was prepared in two steps by reaction of 2-(2-cyano-acetylamino)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxamide (1) with phenyl isothiocyanate and chloroacetyl chloride, which diazocoupled with p-tolyldiazonium chloride in pyridine to afford the corresponding hydrazono derivative 4. Also, condensation of 3 with p-anisaldehyde gave the corresponding arylidine derivative 5. Treatment of 2 with dimethyl sulfate afforded the ketene N,S-acetal 9 which give 5-amino pyrazole derivative 10 upon treatment with hydrazine hydrate. Compound 10 was used as key intermediate for synthesis of pyrazolo[5,1-c][1,2,4]triazine 13a, b, pyrazolo[5,1-a]pyrimidine 14-17 and pyrolo pyrazole 18 derivatives. Finally, condensation of 1 with DMF-DMA afforded the corresponding acryloamide derivative 19, which afforded the corresponding pyrazole derivative 20 upon heating with hydrazine hydrate. All new synthesized compounds were evaluated as antimicrobial agents; some of them exhibited promising activities.
2-(5-氧代噻唑烷酮)-氰基乙酰胺衍生物 3 通过 2-(2-氰基乙酰胺基)-4,5,6,7-四氢苯并[b]噻吩-3-甲酰胺（1）与苯基异硫氰酸酯和氯乙酰氯反应两步制备，然后与对甲苯重氮盐酸盐在吡啶中偶联得到相应的腙衍生物 4。此外，3 与对甲氧基苯甲醛缩合得到相应的芳基亚甲基衍生物 5。2 与硫酸二甲酯反应得到偕二酮 N,S-缩醛 9，后者与水合肼反应得到 5-氨基吡唑衍生物 10。化合物 10 被用作合成吡唑并[5,1-c][1,2,4]三嗪 13a、b、吡唑并[5,1-a]嘧啶 14-17 和吡咯并吡唑 18 衍生物的关键中间体。最后，1 与 DMF-DMA 缩合得到相应的丙烯酰胺衍生物 19，后者与水合肼加热得到相应的吡唑衍生物 20。所有新合成的化合物都被评估为抗菌剂；其中一些表现出有希望的活性。
