(+/-)-3-(4-Amino-1H-pyrrolo[2,3-d]pyrimidin-1-yl)-5-(hydroxymethyl)- (1 alpha,2 alpha,3 beta,5 beta)-1,2-cyclopentanediol, the carbocyclic analogue of tubercidin.
(+/-)-3-(4-Amino-1H-pyrrolo[2,3-d]pyrimidin-1-yl)-5-(hydroxymethyl)- 1 alpha,2 alpha,3 beta,5 beta)-1,2-cyclopentanediol (9), the carbocyclic analogue of tubercidin, prepared from (+/-)-3-amino-5-(hydroxymethyl)-(1 alpha,2 alpha,3 beta,5 beta)- 1,2-cyclopentanediol (6), is cytotoxic to cells containing adenosine kinase but not to cells that do not, indicating that its activity depends on phosphorylation. Although inactive against P388 leukemia in mice and against herpes and influenza viruses in vitro, it showed marginal activity against respiratory syncytial, vesicular stomatitis, and rhino viruses in vitro.
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D000998:Antiviral Agents / Q000138:chemical synthesis; D002294:Carcinoma, Squamous Cell; D002460:Cell Line; D006801:Humans; D007202:Indicators and Reagents; D007822:Laryngeal Neoplasms; D007939:Leukemia L1210 / Q000188:drug therapy; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D012263:Ribonucleosides / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship; D014372:Tubercidin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000633:toxicity
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D007202:Indicators and Reagents; D012263:Ribonucleosides; C040989:3-(4-amino-1H-pyrrolo(2,3-d)pyrimidin-1-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol; D014372:Tubercidin