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Indian Journal of Pharmaceutical Education and ResearchNOW IN
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IJPER · Lens · Synthesis and Evaluation of New Brominated Azaflavones and Azaflavanone Derivatives as Cytotoxic agents against Breast Cancer Cell Line (MCF-7)

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Article · Volume 53, Issue 1 · pp. 117–126

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

Srujana Muthadi1, Baswaraju Macha1, Prashanthi Mamidi2, Sravanthi Manchinella2, Achaiah Garlapati3, Raghuram Rao Akkinepalli4

  1. 1Research Scholar, University College of Pharmaceutical Sciences, Kakatiya University, Warangal, Telangana, INDIA.
  2. 2Project fellow, University College of Pharmaceutical Sciences, Kakatiya University, Warangal, Telangana, INDIA.
  3. 3Professor, University College of Pharmaceutical Sciences, Kakatiya University, Warangal, Telangana, INDIA.
  4. 4(Present Address) Director, National Institute of Pharmaceutical Education and Research (NIPER), SAS Nagar, Punjab, INDIA.

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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