Synthesis and characterization of novel imidazoquinoline based 2-azetidinones as potent antimicrobial and anticancer agents

Abstract

A new series of N-substituted azetidinones (9a–h) synthesized by condensation of 4-arylidene hydrazino 1-isobutyl-1H-imidazo[4,5-c]quinolines (8a–h) with chloroacetyl chloride afforded 4-arylazetidin-2-ones (9a–h). The synthesized compounds were characterized by 1H NMR, 13C NMR, mass spectral and elemental analyses. All synthesized compounds were screened for their in vitro antimicrobial and anticancer activities. The hydrazone derivatives (8a–h) showed good antibacterial activity. Compounds 9a and 9b exhibited good anticancer activity. In a molecular docking study compounds 9a and 9b showed minimum binding energy and good affinity towards the active pocket. Thus, are believed to be good inhibitors of β-tubulin.

Keywords

• Imidazoquinoline
• Hydrazone
• Azetidinone
• Antimicrobial activity
• Anticancer activity
• β-Tubulin
• Docking study