Dipeptide vinyl sultams: Synthesis via the Wittig–Horner reaction and activity against papain, falcipain-2 and Plasmodium falciparum

C Valente, RC Guedes, R Moreira, J Iley, J Gut…

Index: Valente, Claudia; Guedes, Rita C.; Moreira, Rui; Iley, Jim; Gut, Jiri; Rosenthal, Philip J. Bioorganic and Medicinal Chemistry Letters, 2006 , vol. 16, # 15 p. 4115 - 4119

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Citation Number: 42

Abstract

The synthesis of phosphonate derivatives of N-phenyl-and N-benzyl-γ-and δ-sultams, and their application in the Wittig-Horner reaction with N-Boc-l-phenylalanine aldehyde to afford E-and Z-isomers, are described. These compounds were further processed to provide five dipeptide vinyl sultams, which were found to be inactive against papain at concentrations up to 50μM. In contrast, vinyl sultams demonstrated weak activity against recombinant ...