Convenient synthesis and evaluation of enzyme inhibitory activity of several N-Alkyl-, N-Phenylalkyl, and cyclic isourea derivatives of 5a-Carba-α-dl-fucopyranosylamine

Bioorganic & Medicinal Chemistry Letters
2002.0

Abstract

Convenient synthesis and chemical modification of the potent alpha-L-fucosidase inhibitor, 5a-carba-alpha-DL-fucopyranosylamine (1), are described. Among seven N-substituted and three cyclic isourea derivatives newly prepared, the N-octyl derivative was found to be the strongest inhibitor of alpha-L-fucosidase (bovine kidney) more potent (K(i)=0.016 microM) than deoxyfuconojirimycin (K(i)=0.031 microM) with p-nitrophenyl-alpha-L-fucopyranoside as the substrate.

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