SYNTHESIS, CHARACTERIZATION, DOCKING STUDIES AND ANTIMICROBIAL ACTIVITY OF 3-CHLORO-4-(2-OXIDO-2-(4-SUBSTITUTED PHENYL) BENZO [D] [1,3,2] DIOXAPHOSPHOL-5-YL)-1-(QUINOLIN-6-YL)AZETIDINE-2-ONE

Saileela Ramayanam, M. Murali Krishna, Madhavi Devarakonda, Vijay Kumar P.*, L. K. Ravindranath

ABSTRACT

3-chloro-4-(2-oxido-2-phenoxy benzo[d][1,3,2]dioxaphosphol-5-yl)-1-(quinoline-6-yl)azetidin-2-one (7a-g) were synthesized by condensing 3-chloro-4-(3,4-dihydroxy phenyl)-1-(quinoline-6-yl)azetidin-2-one(5) with 4-substituted phenyl phosphorodichloridates(6a-g). The synthon (5) was synthesized by hydrolysis of 3-chloro-4-(3,4-dimethoxy phenyl)-1-(quinoline-6-yl)azetidin-2-one (4). The intermediate (4) was synthesized by condensing 1-(3,4-dimethoxy phenyl)-N-(quinoline-6-yl)methanimine (3) with monochloro acetyl chloride. Starting intermediate (3) was synthesized by condensation reaction between quinoline-6-amine (1) and 3,4-dimethoxy benzaldehyde (2). The target molecule (7a-g) were characterized by IR,1H-NMR,13C-NMR,Mass and elemental analysis. The target molecules were subjected to biological evaluation and docking studies. Some of the derivatives found to have promising activity.

Keywords: Quinolin-6-amine, 3,4-dimethoxy benzaldehyde, 4-substituted phenyl phosphodi chloridates, Monochloro acetyl chloride, Condensation reaction, hydrolysis.