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Synthesis and Enzyme Inhibitory Activities of Highly Functionalized Pyridylmethyl-C-[beta]-D-Glycosides

Several pyridylmethyl-C-[beta]-D-glycosides (3a-3l, 6a, and 6h) were synthesized by refluxing 3-([beta]-D-glucopyranosyl)/([beta]-D-cellobiosyl)-propanones and dicyanobenzylidenes with ammonium acetate in anhydrous toluene in moderate to good yields. The reaction involves a C-C Michael addition of e...

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Bibliographic Details
Published in:Journal of carbohydrate chemistry 2011-04, Vol.30 (3), p.132
Main Authors: Pandey, Vivek Parashar, Jaiswal, Natasha, Srivastava, A K, Shukla, Sanjeev K, Tripathi, Rama Pati
Format: Article
Language:English
Online Access:Get full text
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Summary:Several pyridylmethyl-C-[beta]-D-glycosides (3a-3l, 6a, and 6h) were synthesized by refluxing 3-([beta]-D-glucopyranosyl)/([beta]-D-cellobiosyl)-propanones and dicyanobenzylidenes with ammonium acetate in anhydrous toluene in moderate to good yields. The reaction involves a C-C Michael addition of enamine, formed from glycosyl ketone and ammonium acetate, to the dicayanobenzylidene derivative; subsequent dehydrative cyclization; and oxidative aromatization. Two of these prototypes, compounds 3e and 3k, were deacetylated to the respective glucopyranosyl methyl pyridines 4e and 4k with NaOMe/MeOH. The synthesized compounds were screened for their in vitro α-glucosidase inhibitory activities and one of the compounds showed 20% inhibition as compared to standard drug acarbose displaying 39% inhibition. [PUBLICATION ABSTRACT]
ISSN:0732-8303
1532-2327
DOI:10.1080/07328303.2011.618280