Synthesis of new six- and seven-membered 1-N-iminosugar as promising glycosidase inhibitors

Jabgunde, Amit M. ; Kalamkar, Navnath B. ; Chavan, Sanjay T. ; Sabharwal, Sushma G. ; Dhavale, Dilip D. (2011) Synthesis of new six- and seven-membered 1-N-iminosugar as promising glycosidase inhibitors Bioorganic & Medicinal Chemistry, 19 (19). pp. 5912-5915. ISSN 0968-0896

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.bmc.2011.07.059

Abstract

New six- and seven-membered 1-N-iminosugars were prepared from D-glucose by the stereoselective Michael addition of nitromethane to D-glucose derived α,β-unsaturated ester A followed by one pot reduction of nitro/ester functionality and subsequent amine protection to get N-Cbz protected aminol 6. Hydrolysis of 1,2-acetonide and reductive aminocyclization gave seven membered 1-N-iminosugar 5b. While, hydrolysis of 1,2-acetonide followed by NaIO4 oxidative cleavage and hydrogenation using 10% Pd(OH)2/C, H2 gave six membered 1-N-iminosugar 4a; the hydrogenation using 10% Pd/C-H2 however, gave N-methyl substituted 1-N-iminosugar 4b. The hydrochloride salts of 4a/4b and 5b were found to be specific α-galactosidase and moderate α-glucosidae inhibitors, respectively, in micro molar range.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:1-N-iminosugars; Isofagomine Analogues; Glycosidase Inhibitors; D-Glucose
ID Code:87223
Deposited On:16 Mar 2012 06:16
Last Modified:19 Mar 2012 11:34

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