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■ Synthesis of Pyrrolidine 3,4-Diol Derivatives with Anticancer Activity on Pancreatic Tumor Cells

Frederic Steimer, Ana T. Carmona, Antonio J. Moreno-Vargas, Irene Caffa, Michele Cea, Fabrizio Montecucco, Alessio Nencioni, Pierre Vogel, and Inmaculada Robina*

*Department of Organic Chemistry, University of Seville, Prof. Garcia Gonzalez, 1 Seville-41012, Spain

Abstract

Novel pyrrolidine 3,4-diol derivatives of the type (2R and 2S,3R,4S)-{[((1R)-1-methoxycarbonyl and hydroxylmethyl)-1-arylmethyl)amino]ethyl}-pyrrolidine-3,4-diol have been prepared and evaluated as α-mannosidase inhibitors and assayed for their anticancer activity in vitro. They all exhibit specific but moderate activity as inhibitors towards α-mannosidase from Jack beans. Compounds 7 and 8b bearing hydroxymethyl and trifluoromethylbiphenyl groups show the best antiproliferative effect in two pancreatic cancer cell lines.