Ferrocene as a functional group enhances the inhibitive effect of dihydropyrimidine on radical-induced oxidation of DNA

Abstract

Phenyl and ferrocenyl groups are involved in 3,4-dihydropyrimidin-2(1H)-one (-thione) to form eleven dihydropyrimidines (DHPMs) in this work, aiming to explore the effects of the ferrocene moiety, the CS bond, and the phenolic hydroxyl group on the abilities of DHPMs to protect DNA against 2,2′-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation. It is found that the antioxidant abilities of DHPMs containing CS are higher than those of DHPMs containing CO. In addition, the phenolic hydroxyl group and the CS bond show similar effects on the antioxidant capacities of DHPMs. On the other hand, the ferrocenyl group remarkably increases the antioxidant capacities of DHPMs, while the antioxidant effects of ferrocenyl-appended DHPMs are further improved by the CS bond. Therefore, the influence of the functional group on the antioxidant abilities of DHPMs follows the order: ferrocenyl group > CS bond > phenolic hydroxyl group.