Synthesis and antiangiogenic activity of some novel analogues of 2-[(Z)-2-(4-Nitrophenyl) ethenyl]furan

A series of 2-[(z)-2-(4-nitrophenyl)ethenyl]furan analogues were synthesized in order to obtain new compounds with potential antiangiogenic activity. Base catalysed condensation of p-nitrophenyl acetic acid (3) with furfuraldehyde (2),in the presence of triethylamine, yielded carboxylic acid derivative (4) which on esterification, with methanol, using a catalytic amount of H2SO4, gave corresponding ester derivative (5). Reaction of thionyl chloride with carboxylic acid derivative in refluxing benzene gave the corresponding acid chloride (6), which on subsequent reaction with appropriate amine gave compounds 7a-k. All compounds were evaluated for their antiangiogenic activity by chorioallantoic membrane (CAM) assay method. Compounds 6 and 7h showed pronounced antiangiogenic activity, however, they were less active than standard (β-1,4-galactan sulphate). All other compounds showed significant inhibition of angiogenesis when compared to control but they were much less active than standard. As some of 2-[(z)-2-(4- nitrophenyl)ethenyl]furan analogues showed significant antiangiogenic activity,this moiety may be further explored to find new antiangiogenic leads.