Preparation and biological evaluation of some 1,2-O-isopropylidene-D-hexofuranose esters.
The synthesis and biological evaluation of some new glycose esters bearing the 1,2-O-isopropylidene-d-hexofuranose functionality and belonging to the 3-O-acyl-d-allose and 6-O-acyl-d-glucose series are reported. When the results concerning cell growth inhibition are compared, it appears that the 6-O-acyl-d-glucose derivatives are more active than the 3-O-acyl-d-allose compounds. Within both 6-O-acyl-d-glucose and 3-O-acyl-d-allose derivatives, butyric esters displayed the highest inhibitory effects. Inhibition of cell growth is not associated with high induction levels of erythroid differentiation, despite the fact that pivaloates induce erythroid differentiation to an extent similar to that exhibited by previously reported molecules [Bioorg. Med. Chem. Lett.1999, 9, 3153-3158].
Catelani
Giorgio
G
Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno, 33, I-56126 Pisa, Italy. giocate@farm.unipi.it
D'Andrea
Felicia
F
Landi
Martina
M
Zuccato
Cristina
C
Bianchi
Nicoletta
N
Gambari
Roberto
R
D000080:Acetals / Q000138:chemical synthesis* / Q000494:pharmacology*; D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D002236:Carbohydrate Conformation; D049109:Cell Proliferation / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006601:Hexoses / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D020014:K562 Cells
D000080:Acetals; D000475:Alkenes; D000970:Antineoplastic Agents; D004952:Esters; D005663:Furans; D006601:Hexoses; C013658:propylene