synthesis and antitumor activity of 2-deoxyribofuranosides of 3-deazaguanine.
Synthesis of 2-deoxyribofuranosides of 3-deazaguanine (IX-XII) has been achieved by a base-catalyzed ring closure of appropriate 2-deoxyribofuranosides of methyl 5(4)-(cyanomethyl)imidazole-4(5)-carboxalate (IV-VII). The separation of isomers and anomers were accomplished by column chromatography and HPLC. The site of glycosidic linkage and the anomeric configurations were established on the basis of C-13 and proton magnetic resonance spectroscopy, as well as UV absorption characteristics. Preliminary results of the antitumor activity of these derivatives, in vitro and in vivo, are described.
D000230:Adenocarcinoma / Q000188:drug therapy; D000818:Animals; D000964:Antimetabolites, Antineoplastic / Q000138:chemical synthesis*; D003855:Deoxyribose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000627:therapeutic use; D005260:Female; D006151:Guanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000627:therapeutic use; D007202:Indicators and Reagents; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008325:Mammary Neoplasms, Experimental / Q000188:drug therapy; D051379:Mice; D008809:Mice, Inbred C3H; D008815:Mice, Inbred Strains; D013329:Structure-Activity Relationship
D000964:Antimetabolites, Antineoplastic; D007202:Indicators and Reagents; D006151:Guanosine; D003855:Deoxyribose