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-4ones (6) were obtained. Results: All the synthesized compounds were characterized by using IR, 1 H 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.
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