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Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1573-4064
ISSN (Online): 1875-6638

Structure-Based Design of Benzimidazole Sugar Conjugates: Synthesis, SAR and In Vivo Anti-inflammatory and Analgesic Activities

Author(s): Ahmed O.H. El-Nezhawy, Samir T. Gaballah, Mohamed A.A. Radwan, Ayman R. Baiuomy and Omar M.E. Abdel-Salam

Volume 5, Issue 6, 2009

Page: [558 - 569] Pages: 12

DOI: 10.2174/157340609790170461

Price: $65

Abstract

A series of 2-methyl-N-substituted-benzimidazoles, bearing hydroxypyrrolidinon-5-yl or hydroxypyrrolidin-2- yl, 2,3:5,6-di-O-isopropylidene-α-D-mannofuranoside, 2,3,5,6-tetrahydroxy-α-D-mannofuranoside, 1:2,5:6-di-O-isopropylidene- α-D-gluco-furanose,3-O-benzyl-6,7-dideoxy-1:2-O-isopropylidene-α-D-xylo-heptofuranos-5-ulose, 3-O-benzyl- 6,7-dideoxy-1,2-dihydroxy-α-D-xylo-heptofuranos-5-ulose, 1,2,5,6-tetrahydroxy-α-D-glucofuranose sugar moieties, were obtained in good yields from 2-methyl N-(trichloroacetamidomethyl)benzimidazole as a donor and carbohydrate residues as acceptor precursors in the presence of catalytic amount of trimethylsilyl trifluoromethanesulfonate (TMSOTf) as Lewis acid. Compounds 6, 7, 10, 13, 15, and 16 showed significant anti-inflammatory and analgesic activities.

Keywords: Benzimidazole, trichloroacetimidate, imidomethylation, anti-inflammatory, analgesic


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