title: 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.
authors: Departamento de Quimica, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal.
authors: Daniela A L
authors: DA
authors: Salgueiro
authors: Cristina E A
authors: CE
authors: Sousa
authors: A Gil
authors: AG
authors: Fortes
authors: M José
authors: MJ
authors: Alves
mesh_terms: D000818:Animals; D061565:Cycloaddition Reaction / Q000379:methods*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D006801:Humans; D007212:Indolizines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
chemical_list: C414749:1-azafagomine; D004791:Enzyme Inhibitors; D007212:Indolizines; D006026:Glycoside Hydrolases