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Current Bioactive Compounds

Editor-in-Chief

ISSN (Print): 1573-4072
ISSN (Online): 1875-6646

Design and Synthesis of Aminocyclopentanol Glycosidase Inhibitors: Modification of Mannostatin A and Trehazolamine

Author(s): Seiichiro Ogawa, Miki Kanto and Chikara Uchida

Volume 6, Issue 1, 2010

Page: [31 - 45] Pages: 15

DOI: 10.2174/157340710790711791

Price: $65

Abstract

Convenient synthesis of the α-mannosidase inhibitor mannostatin A from myo-inositol is described by a method, which is generally applicable for provision of aminocyclopentanols of biological interest. Elucidation of structure-inhibitory activity relationships was carried out by chemical modification, leading to discovery of a very potent amino(methoxy)cyclopentanetriol. Similar studies of the trehalase inhibitor trehazolin stimulated development of a new type of aminocyclopentanol glycosidase inhibitor featuring ring contract mimicking of valiolamine, with implications for understanding of the structure and activity relationships of glycosidase inhibitors of this type.

Keywords: Drug design, glycosidase inhibitors, aminocyclitols, bioactive cyclitols, natural product syntheses, diastereoselective synthesis, chemical modification, structure-inhibitory activity relationships


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