Synthesis and Evaluation of New Brominated Azaflavones and Azaflavanone Derivatives as Cytotoxic agents against Breast Cancer Cell Line (MCF-7)

Indian Journal of Pharmaceutical Education and Research

  • Srujana Muthadi1Research Scholar, University College of Pharmaceutical Sciences, Kakatiya University, Warangal, Telangana, INDIA.
  • Baswaraju Macha1Research Scholar, University College of Pharmaceutical Sciences, Kakatiya University, Warangal, Telangana, INDIA.
  • Prashanthi Mamidi2Project fellow, University College of Pharmaceutical Sciences, Kakatiya University, Warangal, Telangana, INDIA.
  • Sravanthi Manchinella2Project fellow, University College of Pharmaceutical Sciences, Kakatiya University, Warangal, Telangana, INDIA.
  • Achaiah Garlapati3Professor, University College of Pharmaceutical Sciences, Kakatiya University, Warangal, Telangana, INDIA.
  • Raghuram Rao Akkinepalli4(Present Address) Director, National Institute of Pharmaceutical Education and Research (NIPER), SAS Nagar, Punjab, INDIA.

Volume 53 Issue 1 Pages 117-126

DOI: 10.5530/ijper.53.1.16

Abstract

Background: Flavonoids encompasses flavones, isoflavones, flavanones and flavanols each possessing the benzopyranone ring system as the common structural feature, were identified as potent nonsteroidal aromatase inhibitors (NSAIs). Purpose: Azaflavones which were isosteric structural scaffolds of flavonoids were also proven to be potent NSAIs. In order to develop new NSAIs as cytotoxic agents for breast cancer, we designed some 6-bromo-2-substituted azaflavanones and azaflavone derivatives. Method: Azaflavones and Azaflavonones were synthesized by a reaction of 2-amino-6-bromoacetophenone and various aromatic aldehydes to result in different chalcones (4) using Claisen-Schmidt condensation. Further cyclization of chalcones (4), led to tetrahydroquinoline-4-ones (5) using orthophosphoric acid. In the final oxidative step, the desired dihydroquinoline-4- ones (6) were obtained. Results: All the synthesized compounds were characterized by using IR, 1H NMR and ESI-MS data and were evaluated for cytotoxic activity by using MTT assay on MCF-7 cell lines. Conclusion: Compounds with furoyl and pyridyl groups as substituents were found to be potent.

Keywords

  • Azaflavones
  • Azaflavanones
  • Claisen-Schmidt condensation
  • Cytotoxicity
  • MTT assay
  • FT-IR
  • NMR
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