Synthesis and Biological Activity Evaluation of Some Azetidinone and Thiazolidinone Derivatives of Coumarins

Abstract

Keeping in view the pharmacological potential of azetidinones, thiazolidinones and coumarins, the
title compounds containing these nuclei were synthesized. The 4-methyl -7-hydroxy coumarin (1) on treatment with
hydrazine hydrate affords 2-hydrazo- 4-methyl -7-hydroxy coumarin (2). The N- (2’-imino-4’-methyl-7’-hydroxy
coummarinyl)-imino substituted benzene (3) was synthesized by reaction of compound 2 with various aromatic
aldehydes. Condensation of compound 3 with chloroacetyl chloride in presence of 1,4-dioxan and triethyl amine
yields the 3-chloro-4- (substituted)-1-(2’-imino-4’-methyl-7’-hydroxy coumarinyl) azetidin-2-one (4a-d). Further
more condensation of 3 with thioglycollic acid in presence of 1,4-dioxan and anhydrous aluminium chloride gives
2-(substituted phenyl)-3-(2’-imino-4’-methyl-7’-hydroxy coumarinyl)-1,3-thiazolidinone (4’a-d). Elemental and
spectral characterization established the identity of these compounds. All the products were screened in vitro for their
anti microbial activity against different strains of urinary tract pathogens. All compounds exhibited significant
antimicrobial activity compared to the standard drug nitrofurantoin.