Sanap, Shrihari P. ; Ghosh, Sougata ; Jabgunde, Amit M. ; Pinjari, Rahul V. ; Gejji, Shridhar P. ; Singh, Shailza ; Chopade, Balu A. ; Dhavale, Dilip D. (2010) Synthesis, computational study and glycosidase inhibitory activity of polyhydroxylated conidine alkaloids - a bicyclic iminosugar Organic and Biomolecular Chemistry, 8 (14). pp. 3307-3315. ISSN 1477-0520
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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/2010...
Related URL: http://dx.doi.org/10.1039/C004690F
Abstract
New bicyclic conidine iminosugars 1d and 1e were synthesized from D-glucose. Thus, D-glucose was converted to sugar β-amino acids 3a and 3b in good yields. Individual treatment of 3a/3b with the Mukaiyama reagent afforded sugar β-lactams 4a/4b that on reduction with LiAlH4/AlCl3 gave azetidines 5a/5b with a sugar appendage. Reductive aminocyclization of sugar azetidines 5a/5b afforded the corresponding conidine iminosugars 1d/1e. Based on the 1H NMR and DFT calculation studies the conformation of 1d was assigned as half chair A2 and that of 1e as a boat B2. The glycosidase inhibitory activities of 1d and 1e such as α-mannosidase, α-glucosidase and α-galactosidase were studied. The α-amylase activity was compared with acarbose. Compound 1d was found to be a moderate inhibitor of glycosidases while 1e was noticed to be a good inhibitor of α-mannosidase and a moderate inhibitor of other glycosidases. These results were substantiated by molecular docking studies using WHAT IF software and the AUTODOCK 3.0 program.
Item Type: | Article |
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Source: | Copyright of this article belongs to Royal Society of Chemistry. |
ID Code: | 87230 |
Deposited On: | 16 Mar 2012 06:14 |
Last Modified: | 19 Mar 2012 11:32 |
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