Synthesis, characterisation, docking studies and anti-microbial evaluation of ethyl (4-substituted phonoxy)-benzodioxophosphol-4-oxothiazolidin-thiophene-2-carboxylates

Abstract

The reaction of ethyl 3-((3,4-dimethoxybenzylidene)amino) thiophene-2-carboxylate (5) reacts with mercapto acetic acid in presence of zinc chloride in dioxane forms ethyl 3-(2-(3,4-dimethoxyphenyl)-4-oxothiazolidin-3-yl)thiophene-2-carboxamide (6) which on hydrolysis affords the ethyl 3-(3-chloro-2-(3,4-dihydroxyphenyl)-4-oxothiazolidin-3-yl)thiophene-2-carboxylate (7). A new series of ethyl (4-substituted phonoxy)-benzodioxophosphol-4-oxothiazolidin-thiophene-2-carboxylates (9a-g) were synthesized from ethyl 3-(3-chloro-2-(3,4-dihydroxyphenyl)-4-oxothiazolidin-3-yl)thiophene-2-carboxylate (7) by condensing with 4-substituted phenyl phosphoro dichloridates (8a-g). The structures of these analogues (9a-g) have been established by 1H NMR, IR, Mass spectral data and elemental analysis. This study describes the anti-microbial activity and docking studies of newly synthesized analogues (9a-g).