Decoration of dihydropyrimidine and dihydropyridine scaffolds with sugars via Biginelli and Hantzsch multicomponent reactions: an efficient entry to a collection of artificial nucleosides.
Here we present an overview of our work on the glycosylation of biologically relevant heterocycles. An array of stereochemically pure C-glycosylated dihydropyrimidine and dihydropyridine derivatives (artificial nucleosides) has been prepared. Our strategy involved the synthesis of suitably designed C-glycosylated reagents and their use as components in Biginelli and Hantzsch cyclocondensations. Molecular diversity has been explored within the collection on the basis of the nature and the number of sugar residues as well as their positions in the heterocyclic rings.
Dondoni
Alessandro
A
Dipartimento di Chimica, Università di Ferrara, 46-44100 Ferrara, Italy. adn@unife.it
Massi
Alessandro
A
D002241:Carbohydrates; D004095:Dihydropyridines / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D009543:Nifedipine / Q000138:chemical synthesis*; D009705:Nucleosides; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013871:Thiones / Q000138:chemical synthesis*
D002241:Carbohydrates; D004095:Dihydropyridines; D009705:Nucleosides; D011743:Pyrimidines; D013871:Thiones; C400223:monastrol; C038806:1,4-dihydropyridine; D009543:Nifedipine