Diaryl α-nitrostilbenes as nitro-substituted analogues of combretastatins: synthesis and biological evaluation in the sea urchin embryo model

A series of nitro analogues of potent antimitotic combretastatin A-4 (diaryl α-nitrostilbenes, DNSs) was synthesized by the Knoevenagel condensation of arylnitromethanes with methylamine Schiff bases of benzaldehydes. The obtained stilbenes featured only cis-diaryl topology irrespective of substitution pattern in the aryl fragments. The evaluation on a sea urchin embryo model suggested that DNSs exhibited both antitubulin and tubulin-unrelated effects similar to those of corresponding monoaryl nitrostyrenes.