Synthesis and biological evaluation of novel 1'-branched and spironucleoside analogues.
Novel anomeric spironucleosides and 1'-cyano-2',3'-didehydro-2',3'-dideoxyuridine, a structural analogue of known anti-HIV agents, were prepared by nucleophilic addition of organolithium reagents to 1'-cyano-2'-deoxy- and 1'-cyano-2'-deoxy-2'beta-bromo-uridine derivatives, respectively. The yield and distribution of products depended on the reaction conditions, which were studied in detail. Although none of the compounds exhibited antiviral activity, two compounds displayed cytostatic activity against both murine leukemia and human T-lymphocyte cells.
Chatgilialoglu
Chryssostomos
C
Istituto per la Sintesi Organica e la Fotoreattività, Consiglio Nazionale delle Ricerche, Bologna, Italy.
Ferreri
Carla
C
Gimisis
Thanasis
T
Roberti
Marinella
M
Balzarini
Jan
J
De Clercq
Erik
E
D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D002853:Chromatography, Liquid; D002855:Chromatography, Thin Layer; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014961:X-Ray Diffraction
D000998:Antiviral Agents; D009705:Nucleosides