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Acta Pharm ; 59(2): 159-70, 2009 Jun.
Article in English | MEDLINE | ID: mdl-19564141

ABSTRACT

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.


Subject(s)
Antineoplastic Agents/chemical synthesis , Coumarins/chemical synthesis , Drug Design , Free Radical Scavengers/chemical synthesis , Animals , Antineoplastic Agents/pharmacology , Carcinoma, Ehrlich Tumor/pathology , Cell Survival/drug effects , Cells, Cultured , Coumarins/pharmacology , Free Radical Scavengers/pharmacology , Lymphoma/pathology , Mice , Molecular Structure , Structure-Activity Relationship
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