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

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

Journal Name:Current Bioactive Compounds

Volume 6 , Issue 1 , 2010

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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Article Details

VOLUME: 6
ISSUE: 1
Year: 2010
Page: [31 - 45]
Pages: 15
DOI: 10.2174/157340710790711791