SYNTHESIS, CHARACTERISATION, DOCKING STUDIES AND ANTIMICROBIAL EVALUATION OF ETHYL 3-(3-CHLORO-2-(2-OXIDO-2-(4-SUBSTITUTED PHENOXY)BENZO[D]-DIOXAPHOSPHOL-5-YL)-4-OXOAZETIDIN-1-YL)THIOPHENE-2-CARBOXYLATES

Y. N. Spoorthy, P. Vijaya Kumar*, T. Sailaja Rani and L. K. Ravindranath

ABSTRACT

The reaction of ethyl 2-cyanoacetate with 2,5-dihydroxy-1,4-dithiane in presence of catalytic amount of tri ethyl amine in ethanol affords ethyl 3-aminothiophene-2- Carboxylate(3). The later on reaction with 3,4-dimethoxy benzaldehyde(4) in presence of few drops of acetic acid to form ethyl 3-((3,4-dimethoxybenzylidene)amino) thiophene-2-Carboxylate(5). Further the inter mediate(5) reacts with Monochloro acetyl chloride in presence of triethyl amine in dioxane forms ethyl 3-(3-chloro-2-(3,4-dimethoxy phenyl)-4-oxoazetidin-1-yl)thiophene-2- Carboxylate(6). Which on hydrolysis affords the ethyl 3-(3-chloro-2-(3,4-dihydroxyphenyl)-4-oxoazetidin-1-yl)thiophene-2-Carboxylate(7). A new series of ethyl 3-(3-chloro-2-(2-oxido-2-(4-substituted phenoxy)benzo[d]-dioxaphosphol-5-yl)-4-oxoazetidin-1-yl)thiophene-2-carboxylates (9a-g) were synthesized from ethyl 3-(3-chloro-2-(3,4-dihydroxyphenyl)-4-oxoazetidin-1-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).

Keywords: Ethyl-2-cyanoacetate, 2,5-dihydroxy-1,4-dithiane, 3,4-dimethoxy benzaldehyde, Monochloro acetyl chloride, 4-substituted phenols , antimicrobial activity and docking studies.