Structural characterization, electronic properties, and anxiolytic-like effect in adult zebrafish (Danio rerio) of cinnamaldehyde chalcone

Abstract Zebrafish is a model animal that is used for neurobehavioral studies. It is an excellent model organism for pharmacological studies and/or safety research at an early stage of drug development. In this work, the chalcone (2E, 4E)-1-(2‑hydroxy-3,4,6-trimethoxyphenyl)-5-phenylpenta-2,4‑dien‑1-one, was synthesized by the Claisen-Schmidt condensation from two natural products: 2‑hydroxy-3,4,6-trimethoxyacetophenone and cinnamaldehyde. The molecular structure of this compound was confirmed by spectroscopic methods such as NMR, Infrared, UV–vis, and quantum chemical calculations. In addition, the anxiolytic-like effect of the cinnamaldehyde chalcone in adult zebrafish (Danio rerio) was evaluated. The results showed that chalcone caused an approximately 80% reduction in zebrafish locomotor activity and induced maximum permanence of zebrafish in the clear zone (61.16%) at a dose of 0.5 mg kgl−1. The data suggest that the cinnamaldehyde chalcone has anxiolytic activity.