Synthesis and biological activity of a new class of sulfone-linked pyrrolylpyrazoles and pyrrolylisoxazoles from methyl-3-aryl-2-(E- arylethenesulfonyl)acrylate

Abstract

A new class of sulfone-linked bis heterocycles, methyl-3-(4′-aryl- 1′H-pyrazol-3′-ylsulfonyl)-4-aryl-3H-pyrrole-3-carboxylate (8), methyl-3-(1′-phenyl-3′,5′-diaryl-1′H-pyrazol-4′- ylsulfonyl)-4-aryl-3H-pyrrole-3-carboxylate (9) and methyl-3-(3′,5′- diarylisoxazol-4′-ylsulfonyl)-4-aryl-3H-pyrrole-3-carboxylate (10) were prepared by the regioselective reaction of methyl-3-aryl-2-(E- arylethenesulfonyl)acrylate (2) with tosylmethyl isocyanide followed by fuctionalization of olefin moiety with 1,3-dipolar reagents. The lead compounds were tested for their antimicrobial activity. © 2009 Pharmaceutical Society of Japan.