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Synthesis of 3-(o-stilbenyl)sydnone and 3-(o-stilbenyl)-4-substituted-sydnone derivatives and their antitumor evaluation

A series of novel stilbene-sydnone derivatives were synthesized by the following sequence of reactions: starting from methyl anthranilate via glycine- and nitrosoglycine derivatives the corresponding 3-(o-carbomethoxyphenyl)-4-H/Me/Ph-sydnones were prepared and transformed to 3-(o-formylphenyl)-4-H/Me/Ph-sydnones, starting materials for Wittig reaction with various phosphonium salts to stilbenylsydnone derivatives. Final products were evaluated for their cytotoxic properties on five cancer cell lines, whereby the cis-4-methyl-3-[2-[2-(4-methylphenyl)ethenyl]phenyl]sydnone (5) and cis-4-phenyl-3-[2-[2-(4-chlorophenyl)ethenyl]-phenyl]sydnone (10) showed the most pronounced activity.

stilbenes ; sydnones ; synthesis ; antitumor evaluation

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