SYNTHESIS, CHARACTERIZATION, DOCKING STUDIES AND ANTIMICROBIAL EVALUATION OF 3-(3-CHLORO)-2-(2-OXIDO)-(4-SUBSTITUTED PHENYL)-UREIDO-BENZO[D][1,3,2]DIOXAPHOSPHOL-5-YL-4-OXOAZETIDIN-1-YL)THIOPHENE-2-CARBOXAMIDES AND CARBAMOYL THIOPHENE-CHLORO-4-OXOAZETIDIN-DIOXAPHOSPHOL-(MORPHOLINE/PIPERIDINE/4-METHYL PIPERIZINE)-CARBOXAMIDES

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

ABSTRACT

3-(3-chloro)-2-(2-oxido)-(4-substituted phenyl)-ureido-benzo[d][1,3,2]dioxaphosphol-5-yl-4-oxoazetidin-1-yl)thiophene-2-carboxamides (9a-f) were synthesized by condensing 3-(3-chloro-2-(3,4-dihydroxyphenyl)-4-oxoazetidin-1-yl)thiophene-2-carboxamide(7) with 4-substituted phenyl-carbamido-phosphoric acid dichlorides (8a-f). Similarly carbamoyl thiophene-chloro-4-oxoazetidin-dioxaphosphol Morpholine/Piperidine/4-methyl piperizine-carboxamides (9g-i) were synthesized by condensing (7) with Morpholinyl/Piperidinyl/N-methyl piperizinyl-carbamido-phosphoric acid dichlorides (8g-i). The synthon(7) was synthesized by hydrolysis of 3-(3-chloro-2-(3,4-dimethoxyphenyl)-4-oxoazetidin-1-yl)thiophene-2-carboxamide(6). The intermediate (6) was synthesized by condensing 3-((3,4-dimethoxybenzylidene)amino)thiophene-2-carboxamide(5) with monochloro acetyl chloride in the presence of triethyl amine in dioxane. The synthon(5) was synthesized by reaction between 3-aminothiophene-2-caroxamide(3) and 3,4-dimethoxybenzaldehyde(4) in the presence of few drops of acetic acid. Starting intermediate (3) was synthesized by condensation reaction between 2-cyano acetamide(1) and 1,4-dithiane-2,5-diol(2) in the presence of catalytic amount of tri ethyl amine in ethanol. The target molecules (9a-i) were characterized by IR, 1H-NMR, 13C-NMR, Mass and elemental analysis. The target molecules were subjected to biological evaluation and docking studies. The results observed in the present investigation were reported in this present research article.

Keywords: 2-cyanoacetamide, 1,4-dithiane-2,5-diol, 4-substituted phenyl-carbamido-phosphoric acid dichlorides, Morpholine/Piperidine/4-methyl piperizine-carboxamides, Monochloro acetyl chloride, condensation reaction, hydrolysis.