Issue 9, 2005
From the journal:

Organic & Biomolecular Chemistry

Synthesis and evaluation of the glycosidase inhibitory activity of 5-hydroxy substituted isofagomine analogues

Mohammed M. Matin,a   Tarun Sharma,b   Sushma G. Sabharwalb  and  Dilip D. Dhavale*c  

* Corresponding authors

a Department of Chemistry, University of Chittagong, Chittagong 4331, Bangladesh

b Division of Biochemistry, Department of Chemistry, University of Pune, Pune 411 007, India

c Garware Research Centre, Department of Chemistry, University of Pune, Pune 411 007, India
E-mail: ddd@chem.unipune.ernet.in
Fax: +91-20-2569-1728

Abstract

An efficient strategy for the synthesis of 5-hydroxy substituted isofagomine analogues 4a, 4b and 4c, having both –CH2OH/CH3 and –OH functionality at the C-5 position, and evaluation of their inhibitory potency is reported. The synthetic methodology involves the aldol–Cannizzaro reaction of easily available α-D-xylopentodialdose followed by hydrogenolysis to afford the triol 5. Selective amidation of the α- and β-hydroxymethyl group at C-4, deprotection of the 1,2-acetonide group and hydrogenation gave the target molecules, which were found to be potent against β-glycosidases with IC50 values in the micro molar range. Compound 4c showed excellent potency against glycosidases and human salivary amylase.

Graphical abstract: Synthesis and evaluation of the glycosidase inhibitory activity of 5-hydroxy substituted isofagomine analogues

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Article information

DOI
https://doi.org/10.1039/B418283A
Article type
Paper
Submitted
03 Dec 2004
Accepted
16 Feb 2005
First published
29 Mar 2005

Org. Biomol. Chem., 2005,3, 1702-1707

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Synthesis and evaluation of the glycosidase inhibitory activity of 5-hydroxy substituted isofagomine analogues

M. M. Matin, T. Sharma, S. G. Sabharwal and D. D. Dhavale, Org. Biomol. Chem., 2005, 3, 1702 DOI: 10.1039/B418283A

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