Diels-Alder Cycloaddition in the Synthesis of 1-Azafagomine, Analogs, and Derivatives as Glycosidase Inhibitors

Author(s): Daniela A.L. Salgueiro, Cristina E.A. Sousa, A. Gil Fortes, M. Jose Alves.

Journal Name: Mini-Reviews in Medicinal Chemistry

Volume 12 , Issue 14 , 2012

Abstract:

This comprehensive review deals with the synthesis of 1-azafagomine, analogs, and derivatives having the Diels-Alder cycloaddition as the key step. Most of the compounds referred are racemic or have been resolved by lipase transesterification. There are two asymmetric cycloadditions leading to 1-azafagomine or to an analog. In one case both enantiomers of 1-azafagomine were prepared together with a pair of derivatives. The study comprises glycosidase inhibition studies of the target compounds to a set of glycosidic enzymes, and evidenced molecular features that enhance or diminish their activity as glycosidase inhibitors.

Keywords: Azafagomine, biological activity, Diels-Alder cycloaddition, glycosidase inhibitors, azasugars, Monocyclic Analogs, α-mannosidases

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Article Details

VOLUME: 12
ISSUE: 14
Year: 2012
Page: [1465 - 1476]
Pages: 12
DOI: 10.2174/138955712803832663
Price: $58

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