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

[ Vol. 5 , Issue. 6 ]

Author(s):

Ahmed O.H. El-Nezhawy, Samir T. Gaballah, Mohamed A.A. Radwan, Ayman R. Baiuomy and Omar M.E. Abdel-Salam   Pages 558 - 569 ( 12 )

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

Affiliation:

Chemistry of Natural and Microbial Products Department, National Research Center, Dokki, Cairo, Egypt.



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