Synthesis, Characterization and Antimicrobial Evaluation of Bisphosphates with Bis-3-chloro-4-oxoazetidin System Derived from Optically Active Tartaric Acid

The target molecules bisphosphates of bis-3-chloro-4-oxoazetidin system (8a-g) weresynthesized by reacting (2R,3R)- N^1, N^4-bis (2-(4-substituted phenyl)-3-chloro-4-oxoazetidin-1- yl)-2,3-dihydroxysuccinamide (6a-e) with different bis/di(alkyl)chlorophosphates (7a-c) in the presence of Et3N in dry toluene / THF solvent mixture. Bis-3-chloro-4-oxoazetidin system was obtained from optically active diethyl tartarate (1). Its hydrazide (3) on reaction with 4-substituted benzaldehyde gave benzylidene derivatives (4a-e) which were further allowed to undergo condensation with chloroacetyl chloride in triethylamine and dry 1,4-dioxane to afford (6a-e). The structure of these newly synthesized products (8a-g) were confirmed from their IR, ^1H-NMR, ^13CNMR, ^31P-NMR and Mass Spectral data. The antimicrobial activities of these compounds (8a-g) were evaluated and they exhibited significant antimicrobial activity.