Synthesis, Characterization and Antimicrobial Activity of Novel 2-Azetidinones Compounds

Abstract

A series of 2-azetidinone derivatives were synthesized by the formation of triazole, followed by synthesis of Schiff’s bases by condensation of various substituted aldehydes. The Schiff’s bases further reacted to chloroacetyl chloride in the presence of triethyl amine, and undergoes cyclocondensation to give substituted 3-chloro-1-(3-mercapto-5-((5-methoxy-1H-indol-1-yl)methyl)-4H-1,2,4-triazol-4-yl)-4-phenylazetidin-2-one which on further reaction with ethyl chloroacetate, gives substituted ethyl 2-((4-(3-chloro-2-oxo-4-phenylazetidin-1-yl)-3-((5-methoxy-1H-indol-1-yl)methyl)-4,5-dihydro-1H-1,2,4-triazol-5-yl)thio)acetate. Synthesized compounds were by characterized by fourier-transform infrared (FTIR), nuclear magnetic resonance (NMR) (1H, 13C), and mass spectroscopy. All synthesized compounds were evaluated for its in-vitro antimicrobial activity against Gram-positive and gram-negative bacterial as well as fungal strains. The antimicrobial activity results revealed that A-VI, A-IX, A-XVIII, displayed equipotent activity when compared with the standard drug. The compounds with p-chloro and p-nitro group exhibited the most potent antimicrobial agent.