AMBERLITE IRA 67 CATALYZED DARZENS REACTION: SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL STUDY OF NOVEL 3-SUBSTITUTED BENZYL-2-OXIRANES

Abstract

In the present work, five novel 3-substituted benzyl-2-oxiranes were synthesized from 2chloroacethophenone and aldehydes in the presence of Amberlite IRA 67 catalyst by Darzens reaction method. The structures of the as-synthesized compounds were characterized by using IR and NMR techniques such as 1H NMR, 13C NMR and DEPT-135. The as-synthesized compounds were tested against four bacterial species (two gram-negative and two grampositive bacteria) and two fungal species (Fusarium moniliforme and Aspergillus niger) using the paper disc diffusion method and the antitubarcular activity were tested against mycobacterium tuberculosis using the agar microdilution method. The mean zone inhibition of chloramphenicol (antibacterial) and tilt (antifungal) were referred to as a reference (in mm). (3-(4-(dimethylamino)phenyl)oxiran-2-yl)(phenyl)methanone showed greater antifungal activity against both tested fungi than all the other as-synthesized compounds. (3-(Indol-3yl)oxiran-2-yl)(phenyl)methanone and (3-(2-nitrophenyl)oxiran-2-yl) (phenyl)methanone showed good inhibition zone against Aspergillus niger and Fusarium moniliforme, respectively. The (3-(2-nitrophenyl)oxiran-2-yl)(Phenyl)methanone and (3-(4(dimethylamino)phenyl)oxiran-2-yl)(phenyl)methanone were also subjected to test their antitubercular activity and the results showed that the (3-(2-nitrophenyl)oxiran-2yl)(phenyl)methanone was very active at minimum concentration (1.56MIC(µg/mL)) against M.tuberculosis. Amberlite IRA 67 catalyzed Darzens reaction is the best methodologies to synthesis oxirane derivatives in good yield at room temperature.