Synthesis of coumarin heterocyclic derivatives with antioxidant activity and in vitro cytotoxic activity against tumour cells.
The aim of the present work was to synthesise coumarinyl heterocycles and to elucidate the potential role of these compounds as antioxidants and cytotoxic agents against Dalton's lymphoma ascites tumour cells (DLA) and Ehrlich ascites carcinoma cells (EAC). The synthesis of coumarin derivatives containing pyrazole, pyrazolone, thiazolidin-4-one, 5-carboxymethyl-4-thiazolidinone and 3-acetyl-1,3,4-oxadiazole ring is reported. 4-Methylcoumarinyl-7-oxyacetic acid hydrazide (1) reacted with arylazopropanes or hydrazono-3-oxobutyrate derivatives to form pyrazole (3a-c) and pyrazolone derivatives (5a-c). Heterocyclisation of Schiff's bases of 1 with thioglycolic acid, thiomalic acid or acetic anhydride afforded novel heterocyclic derivatives 4-thiazolidinones (7a-c), 5-carboxymethyl-4-thiazolidinones (8a-c) and oxadiazoles (9a-c), respectively. Some of the compounds showed promising antioxidant activity in vitro and cytotoxic activity against DLA cells and EAC cells.
Manojkumar
Parameswaran
P
Department of Pharmaceutical Chemistry, College of Pharmacy, Sri Ramakrishna Institute of Paramedical Sciences, Coimbatore-641044, Tamilnadu, India. kmano1975@rediffmail.com
Ravi
Thengungal Kochupappy
TK
Subbuchettiar
Gopalakrishnan
G
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002286:Carcinoma, Ehrlich Tumor / Q000473:pathology; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D003374:Coumarins / Q000138:chemical synthesis* / Q000494:pharmacology; D015195:Drug Design; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000494:pharmacology; D008223:Lymphoma / Q000473:pathology; D051379:Mice; D015394:Molecular Structure; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D003374:Coumarins; D016166:Free Radical Scavengers