Synthesis and Biological Evaluation of (4-Fluorophenyl)(1-(5-phenyl-1,3,4-oxadiazol-2-yl)indolizin-3-yl)methanone Derivatives as Anti-cancer and Antimicrobial Agents

T.R Ravikumar Naik; G Mahanthesha; T Suresh

doi:10.25004/IJPSDR.2022.140102

T.R Ravikumar Naik Department of P. G. Studies in Chemistry, Veerashaiva College, Vijayanagara Sri Krishnadevaraya University, Cantonment, Ballari, Karnataka-583105, India
G Mahanthesha Department of Chemistry, Vijayanagara Sri Krishnadevaraya University, Jnana Sagar, Vinayakanagar, Cantonment, Ballari, Karnataka-583105, India.
T Suresh Department of Chemistry, Vijayanagara Sri Krishnadevaraya University, Jnana Sagar, Vinayakanagar, Cantonment, Ballari, Karnataka-583105, India.

DOI: https://doi.org/10.25004/IJPSDR.2022.140102

Keywords: 1,3,4-Oxadiazole, Anticancer, Antibacterial activity, Antifungal activity, Indolizines.

Abstract

A novel series of (4-Fluorophenyl (1-(5-phenyl-1,3,4-oxadiazol-2-yl)indolizin-3-yl)methanone derivatives 9(a-n) were synthesized by the coupling reaction of 3-(4-fluorobenzoyl)indolizine-1-carboxylic acid and substituted benzohydrazide followed by intramolecular cyclization. The structures of the compounds were characterized by 1 H NMR, 13C NMR, LCMS, FT-IR, and elemental analyses. The compounds 9(a-n) anti-cancer activity was evaluated against the MCF-7 cell line (HTB-22, Homo sapiens, Breast carcinoma). Compound 9j (IC50 = 21.57 µM), and 9n (IC50 = 8.52 µM) exhibited the most potent cytotoxicity activity compared with standard drug doxorubicin (IC50= 25.71). The antibacterial activity was evaluated against Staphylococcus aureus ATCC 6538 and Escherichia coli ATCC 8739. The compounds ZOI=16mm) and 9i (ZOI=18 mm) exhibited moderate antibacterial activity compared with standard drug ciprofloxacin. The antifungal activity was evaluated against Candida albicans ATCC 10231. Most compounds exhibited moderate antifungal activity compared with the standard drug Itraconazole.