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

作者：Valente Claudia; Guedes Rita C; Moreira Rui; Iley Jim^*; Gut Jiri; Rosenthal Philip J

来源：Bioorganic & Medicinal Chemistry Letters, 2006, 16(15): 4115-4119.

DOI：10.1016/j.bmcl.2006.04.079

• Wittig-Horner reaction
• vinyl sultams
• papain
• antimalarials
• cysteine proteases
• falcipain-2
• Plasmodium falciparum
• molecular modelling

The synthesis of phosphonate derivatives of N-phenyl- and N-benzyl-gamma and delta-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 50 mu M. In contrast, vinyl sultams demonstrated weak activity against recombinant falcipain-2 and Plasmodium falciparum W2.

• 出版日期2006-8-1