Acta Pharm. 59 (2009)
159-170
Original research paper
Synthesis of coumarin
heterocyclic derivatives with antioxidant activity and in vitro cytotoxic activity against tumour cells
PARAMESWARAN MANOJKUMAR, THENGUNGAL KOCHUPAPPY RAVI and SUBBUCHETTIAR
GOPALAKRISHNAN
kmano1975@rediffmail.com
Department of Pharmaceutical Chemistry, College of
Pharmacy, Sri Ramakrishna Institute of Paramedical Sciences, Coimbatore-641044,
Tamilnadu, India
Accepted April 3, 2009
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 Schiffs 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 results in in vitro antioxidant activity and
cytotoxic activity against DLA cells and EAC cells.
Keywords: pyrazole, pyrazolone, thiazolidin-4-one, oxadiazole, antioxidant
activity