Chalcones have been an important synthetic target for decades. There is a wide array of chalcone derivatives that have been found in nature and/or synthetically obtained. This α,β-unsaturated system with two aromatic substituents allows many synthetic possibilities. Herein, one of the aromatic moieties will be organometallic ferrocene, while the other aromatic moiety will be biologically relevant heterocycles. The ferrocene group is stable in both aqueous and aerobic environments, an important property for potential drug candidates and their bioavailability. For their part, heterocycles including pyrimidine, thiophene, thiazolyl and indole groups have been reported to have encouraging biological potential. Therefore, ferrocene–heterocycle containing chalcones could be promising drug candidates. System 1 ferrocenyl chalcones bear the ferrocene group at the 1’ while system 3 ferrocenyl chalcones bear the ferrocene group at the 3’ position with respect to the carbonyl group. Both system 1 and system 3 ferrocenyl chalcones were synthetized by solvent free or alcoholic Claisen–Schmidt condensation conditions with moderate yields. Compounds were characterized via <sup>1</sup>H-NMR and <sup>13</sup>C-NMR spectroscopy. The effect of varying heterocycles in the same position as well as the effect of interchanging aromatic substituents in position 1’ and position 3’ was evaluated by comparing biological activity against breast cancer cell line MDA-MB-231 and antioxidant activity of system 1 and system 3 ferrocenyl chalcones. [5R25GM061151-20]

Synthesis, characterization and biological evaluation of heterocyclic ferrocenyl chalcones

ACS Spring 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.