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Note | Regular issue | Vol 68, No. 4, 2006, pp.787-799
Published online, 7th March, 2006
DOI: 10.3987/COM-06-10665
Synthesis of 3-Cyanoflavones and Their Biological Evaluation

Frederic Lassagne, Isabelle Bombarda, Michel Dherbomez, Sourisak Sinbandhit, and Emile M. Gaydou*

*Phytochemistry Laboratory of Marseilles, Saint Jerome Faculty of Sciences and Technology, Paul Cezanne University, Escadrille Normandie Niemen avenue,13397 Marseille Cedex 20, France

Abstract

The synthesis, using β-bromo-α-ethylthiocinnamonitrile (1) and methyl salicylate (2), of two new series of methyl 2-(2’-cyano-2’-ethylthio-1’-phenylvinyloxy)benzoates (3), precursors of 3-cyanoflavones (4) is reported. Compounds (3) and (4) were checked against representatives Gram-positive and -negative bacteria (Escherichia coli, Staphylococcus aureus and Enterococcus hirae). These compounds were quite inactive against bacteria, which is not the case for the two fungi strains investigated (Candida albicans and Saccharomyces cerevisiae). The presence of a 4’-substituent on the 3-cyanoflavone skeleton gives a different effect for S. cerevisiae. The presence of a methylendioxy substituent on the methyl 2-(2’-cyano-2’-ethylthio-1’-phenylvinyloxy)benzoates (3) enhance the effect in particular for C. albicans.