A new approach for the synthesis of bioactive heteroaryl thiazolidine-2,4-diones

Journal of the Brazilian Chemical Society

El-Gohary, Naser Mohamed¹  Ain Shams University, Roxy, Egypt¹  Abdel-Hamed, Mohamed Abdel-Megid¹  Ibrahim, Magdy Ahmed¹ 

关键词: 2;    4-thiazolidinedione;    chromone;    Michael addition;    cyclocondensation;    RORC;    heterocyclic synthesis;   

DOI  :  10.1590/S0103-50532011000600019

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

Condensation of 3-formylchromone (1) with thiazolidine-2,4-dione (2) afforded 5-[4-oxo-4H-chromen-3-yl)methylene]-1,3-thiazolidine-2,4-dione (3). Reaction of 3 with hydrazine hydrate, phenyl hydrazine and hydroxylamine hydrochloride gave the corresponding pyrazole and isoxazole derivatives 4-7. Compound 3 was subjected to react with thiourea, guanidine and cyanoguanidine to give the corresponding pyrimidine derivatives 8-10. Pyrimido[1,2-a]pyrimidine 12, benzo[1,5]diazepine 15, pyrido[1,2-b][1,2,4]triazepine 16, 1,2,4-triazolo[3,4-b][1,3,4]thiadiazepine 19 and 1,2,4-triazino[3,2-b][1,3,4]thiadiazepine 20 linked thiazolidine-2,4-dione were prepared from the reaction of 3 with N,N- and N,S- bifunctional nucleophiles. The chemical reactivity of 3 towards carbon nucleophiles gave new heterocyclic moieties linked thiazolidine-2,4-dione 22‑25. The synthesized compounds were screened in vitro for their antimicrobial activities against Staphylococcus aureus, Proteus vulgaris and Candida albicans.

【 授权许可】

Unknown