Synthesis and Evaluation of New Brominated Azaflavones and Azaflavanone Derivatives as Cytotoxic agents against Breast Cancer Cell Line (MCF-7)
Year: 2019
Type: article
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-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.
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
OpenAlex ID: W2903485352