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Issue 14, 2010
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Synthesis, computational study and glycosidase inhibitory activity of polyhydroxylated conidine alkaloids—a bicyclic iminosugar

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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.

Graphical abstract: Synthesis, computational study and glycosidase inhibitory activity of polyhydroxylated conidine alkaloids—a bicyclic iminosugar

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Supplementary files

Article information


Submitted
26 Mar 2010
Accepted
13 May 2010
First published
02 Jun 2010

Org. Biomol. Chem., 2010,8, 3307-3315
Article type
Paper

Synthesis, computational study and glycosidase inhibitory activity of polyhydroxylated conidine alkaloids—a bicyclic iminosugar

S. P. Sanap, S. Ghosh, A. M. Jabgunde, R. V. Pinjari, S. P. Gejji, S. Singh, B. A. Chopade and D. D. Dhavale, Org. Biomol. Chem., 2010, 8, 3307
DOI: 10.1039/C004690F

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