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

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

Volume: 12 Issue: 14

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

Affiliation:

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

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.

Cite this article as:

A.L. Salgueiro Daniela, E.A. Sousa Cristina, Gil Fortes A. and Jose Alves M., Diels-Alder Cycloaddition in the Synthesis of 1-Azafagomine, Analogs, and Derivatives as Glycosidase Inhibitors, Mini-Reviews in Medicinal Chemistry 2012; 12 (14) . https://dx.doi.org/10.2174/138955712803832663