title: Preparation and biological evaluation of some 1,2-O-isopropylidene-D-hexofuranose esters.
abstract: 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].
authors.affiliation: Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno, 33, I-56126 Pisa, Italy. giocate@farm.unipi.it
authors.forename: Giorgio
authors.initials: G
authors.lastname: Catelani
authors.forename: Felicia
authors.initials: F
authors.lastname: D'Andrea
authors.forename: Martina
authors.initials: M
authors.lastname: Landi
authors.forename: Cristina
authors.initials: C
authors.lastname: Zuccato
authors.forename: Nicoletta
authors.initials: N
authors.lastname: Bianchi
authors.forename: Roberto
authors.initials: R
authors.lastname: Gambari
mesh_terms: 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
chemical_list: D000080:Acetals; D000475:Alkenes; D000970:Antineoplastic Agents; D004952:Esters; D005663:Furans; D006601:Hexoses; C013658:propylene