Design, Synthesis and Biological Evaluation of Stilbene Derivatives Containing a 1,3‐Benzodioxole Moiety

Abstract

Stilbene is an important class of biologically active metabolites with diarylethene scaffold, and which have a broad range of biological activities as the lead for drug discovery. In this study, a novel series of stilbene derivatives bearing 1,3-benzodioxole moiety was designed and synthesized via a convenient method with good to excellent yields, and their structures were characterized by 1 H NMR, 13 C NMR, ESI-MS spectrum. These newly prepared compounds were evaluated for their potential biological activities including fungicidal, insecticidal, and cytotoxic activities.

Synthesis and pyrolysis of methyl cyclopentenolone succinate diester

“…The content of styrene increased from 0.12% to 1.84%, probably due to the dehydration of phenylethanol. Styrene has a special aroma and is often used as an intermediate of medicine, 16 pesticides 17 and dyes 18 …”

Medicinal chemistry perspective on the structure–activity relationship of stilbene derivatives

“…Song et al 21 assessed the cytotoxicity of stilbene derivatives containing a 1,3-benzodioxole moiety. Among the tested compounds, three compounds, 200a , 200b , and 200c , showed activity against HepG-2, but none of them showed activity against the A875 and MARC145 cell lines.…”

“…Song et al 21 synthesized and assessed the fungicidal activity of 1,3-benzodioxole-stilbene derivatives. Compound 27a showed the highest activity against G. theae-sinensis , A. tenuis Nees , F. graminearum , and R. solani .…”

“…Furthermore, phosphate derivatives have demonstrated good activity and have been used in clinical trials. 21 Interestingly, in 2006, Li et al 3 synthesized stilbene derivatives with substituted hydroxyl groups and found that two of these compounds, E -2′,3,5′,5-tetrathydroxystilbene and E -3′,5,5′,6-tetrahydroxystilbene-2-nitrogen, inhibited SARS coronavirus replication using an in vitro model ( Fig. 1 ).…”