Antineoplastic agents. 1. Synthesis and antineoplastic activities of chloroethyl- and methylnitrosourea analogues of thymidine.
A new class of chloroethyl- and methylnitrosourea analogues of thymidine, 5a,b, 6, 10, and 11, has been synthesized from the corresponding amino nucleosides, 2 and 7. The 3'-chloroethyl and 3'-methyl derivatives, 10 and 11, inhibited L1210 cell growth in culture (ED50 = 1.5 and 1.0 micrometer, respectively) more effectively than 1,3-bis(2-chloroethyl)-1-nitrosourea (BCNU) (ED50 = 4 micrometer) and the 5'-nitrosourea analogues. Neither the alkylating nor the carbamoylating activities of these compounds correlated with their biological activity.
D000477:Alkylating Agents / Q000138:chemical synthesis; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D002219:Carbamates / Q000138:chemical synthesis; D002455:Cell Division / Q000187:drug effects; D002478:Cells, Cultured; D055598:Chemical Phenomena; D002621:Chemistry; D007939:Leukemia L1210 / Q000473:pathology; D009607:Nitrosourea Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013936:Thymidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
D000477:Alkylating Agents; D000970:Antineoplastic Agents; D002219:Carbamates; D009607:Nitrosourea Compounds; D013936:Thymidine