The theoretical investigation on properties of paeonol and its isomers

Abstract

Paeonol (2-hydroxy-4-methoxyacetophenone) is the main active ingredient of Traditional Chinese Medicine Moutan Cortex and has a wide range of pharmacological activities. Its isomer 2-hydroxy-5-methoxyacetophenone has also been shown to own the potential for drug. The exploration of the structure and properties of these compounds is helpful for drug design, especially the influence of intramolecular hydrogen bonds on the properties of compounds that medicinal chemists are interested in. In this study, the geometric structure parameters, vibration frequency, topological parameters of electron density, nuclear independent chemical shift, electrostatic potential and reactivity index of paeonol and its isomers in the gas and water phase were calculated by means of quantum chemical calculation (DFT/B3LYP). The equilibrium structure, infrared spectroscopy, intramolecular hydrogen bonding, and reactivity of the two compounds were analysed, and the effect of water solvent was considered. This study reveals the structure and properties of selected compounds at the atomic level and will provide theoretical guidance and inspiration for paeonol-based drug design.