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

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.

Back to (non-)Basics: An Update on Neutral and Charge-Balanced Glycosidase Inhibitors

“…While iminosugars remain currently the most abundant class of glycosidase inhibitors in development, [22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] research into other molecular scaffolds has provided new classes of lead compounds. Neutral (non-ionized at physiologic pH) and charge-balanced (zwitterionic at physiologic pH) glycosidase inhibitors were the subject of our initial review in 2003.…”

Facile Synthesis, Characterization and Anti-Inflammatory Effect of 3-Aminoindolizine Derivatives

“…The functionally substituted indolizines are an important class of heterocycles in many natural and synthetic derivatives [1] due to their great biological and pharmacological activities [2] including anticancer, antiviral, anti-inflammatory, anti-tuberculosis, analgesic and antioxidant effects. In the past decades, the Tschitschibabin reaction, 1,3-dipolar cycloadditions, cyclisation reactions depending on the position of bond formation have been extensively used for the synthesis of these compounds [3].…”