Synthesis and Preliminary in Vitro Biological Evaluation of 4-[(4-Hydroxyphenyl)sulfanyl]but-3-en-2-one, a 4-Mercaptophenol Derivative Designed As a Novel Bifunctional Antimelanoma Agent

Abstract

We report the synthesis and preliminary in vitro biological evaluations of 4-[(4-hydroxyphenyl)sulfanyl]but-3-en-2-one, a compound designed as a potential bifunctional antimelanoma agent, bearing both a tyrosinase-activatable phenolic moiety and a GSH-reactive alpha,beta-unsaturated carbonyl group. Both the E (1) and Z (2) isomers of the synthesized compound proved to be very good substrates of mushroom tyrosinase, reacted quickly with GSH at physiological pH, and showed a significant cytotoxic activity against B16F1 murine melanoma cells.