Synthesis, characterization and antimicrobial evaluation of bisphosphates with Bis-3-chloro-4-oxoazetidin system derived from optically active tartaric acid

Abstract EN

The target molecules bisphosphates of bis-3-chloro-4-oxoazetidin system (8a-g) were synthesized by reacting (2R, 3R)- N1, N4-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.