Antitumor agents. 86. Synthesis and cytotoxicity of alpha-methylene-gamma-lactone-bearing purines.
alpha-Methylene-gamma-lactones covalently linked to adenine, hypoxanthine, and guanine were synthesized by using the convenient Reformatsky-type reaction between ethyl alpha-(bromomethyl)acrylate and the proper purine ketones. In vitro cytotoxicity data demonstrated that these compounds were active against L-1210 tissue culture cells with 3 being most potent (ED50 = 0.3 microgram/mL).
D000225:Adenine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000627:therapeutic use / Q000633:toxicity; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D002470:Cell Survival / Q000187:drug effects; D006147:Guanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000627:therapeutic use / Q000633:toxicity; D006801:Humans; D007042:Hypoxanthines / Q000138:chemical synthesis* / Q000627:therapeutic use / Q000633:toxicity; D007202:Indicators and Reagents; D007624:KB Cells; D007783:Lactones / Q000138:chemical synthesis* / Q000627:therapeutic use / Q000633:toxicity; D007939:Leukemia L1210 / Q000188:drug therapy; D007941:Leukemia P388 / Q000473:pathology; D051379:Mice; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D007042:Hypoxanthines; D007202:Indicators and Reagents; D007783:Lactones; C051628:9-((2-methyl-4-methylene-5-oxotetrahydrofuran-2-yl)methyl)hypoxanthine; C051627:9((2-methyl-4-methylene-5-oxotetrahydrofuran-2-yl)methyl)adenine; C051629:1-((2-methyl-5-methylene-5-oxotetrahydrofuran-2-yl)methyl)guanine; D006147:Guanine; D000225:Adenine