Synthesis of novel trans-stilbene derivatives and evaluation of their potent antioxidant and neuroprotective effects

A convenient synthesis and the biological properties of new amides, esters and other derivatives of trans-stilbene are described. The key synthetic strategies involve the Wittig–Horner reaction of a phosphonium salt 9 and an aldehyde 10 to generate (E)- or (Z)-olefins and a coupling reaction of an acid 12 and various amines 13a–n to give trans-stilbene derivatives 15a–n in high yields. A amide derivative 15g showed three times more in vitro free radical-scavenging activity than resveratrol, while another 15d exhibited strong inhibitory activity against lipopolysaccharide (LPS)a-induced NO generation. Allylamide analogue 15a showed the most potent neuroprotective activity in glutamate-induced primary cortical neuron cells.

Graphical abstracttrans-Stilbene allylamide showed the most potent protective activity against glutamate-induced neurotoxicity and inhibiting the nitrite production.Figure optionsDownload full-size imageDownload as PowerPoint slide