Water-Mediated Synthesis of (<i>E</i>)-3-(1-Methyl-1<i>H</i>-benzo[<i>d</i>]imidazol-5-yl)-<i>N</i>-phenethylacrylamide, a Caffeic Acid Phenethyl Amide Analogue

Abstract

Caffeic acid phenethyl ester (CAPE) is a phenolic natural product with diverse biological activities, notably anticancer properties. However, its ester group is metabolically unstable. The amide derivative, CAPA, offers improved metabolic stability to esterases but still possesses a metabolically liable catechol group. In this work, we describe the synthesis of a novel CAPA analogue in which the catechol is replaced with a benzimidazole bioisostere via a water-mediated Wittig reaction.

Keywords

• anticancer
• natural product
• CAPA
• Wittig reaction
• water-mediated synthesis