Theoretical Analysis of the Properties of Monocarbonyl Curcumin Analogs

Abstract

Curcumin is found in the medicinal plant turmeric and has a wide range of pharmacological activities. To improve their low stability, poor solubility, and low bioavailability, their monocarbonyl derivatives (MACs) modification has received much attention from researchers. In this study, MACs (1a–1e) were investigated with the help of density functional theory (DFT). The equilibrium geometries were optimized and then the predictions of vibration frequencies, conceptual density functional indices, antioxidant activity, and aromaticity were carried out. The results showed that the hydroxyl substitution at o- and p-positions in MACs exhibited strong reactivity, especially the substitution at the p-position significantly improved the electrophilic and antioxidant activity of compounds. This work also found that aqueous solutions had a booster effect on the reactivity of MACs. In contrast, the effect of hydroxyl at the m-position on the structure and properties was not significant. Furthermore, the molecular docking results show that the presence of hydroxyl group in MACs facilitates the enhancement of the interaction between MACs and the receptor. Results of this work introduce new and important information that contributes to the understanding of the potential properties of MACs and provides references and directions for the design of this type of drugs.