Synthesis and antineoplastic activity of CNC-cysteamine and related compounds.
N'-[N-(2-Chloroethyl)-N-nitroso]carbamoyl cysteamine (CNC-cysteamine) and several related compounds have been synthesized and tested against L 1210 leukemia in mice. Reaction of N-(2-chloroethyl)-N-nitrosocarbamoyl azide (CNC-azide) with cysteamine yielded CNC-cysteamine and bis(CNC)cystamine. Reaction of CNC-azide with cystamine in the presence of triethylamine gave bis(CNC)cystamine. Unexpectedly, formation of CNC-cystamine carboxylazide as a minor reaction product was also observed. N-(2-Chloroethyl)carbamoyl cysteamine 2-chloroethylcarbamate was formed when 2-chloroethyl isocyanate was reacted with cysteamine. Nitrosation of this cysteamine N,S-dicarbamoyl derivative led to formation of a mixture of two dinitroso isomers. Preliminary testing of the newly synthesized CNC-derivatives against L 1210 leukemia in mice revealed that CNC-cysteamine, its disulfide bis(CNC)cystamine and CNC-cystamine carboxylazide were highly active against L 1210 leukemia.
D000818:Animals; D000970:Antineoplastic Agents; D003543:Cysteamine; D007939:Leukemia L1210 / Q000188:drug therapy; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D009607:Nitrosourea Compounds / Q000138:chemical synthesis* / Q000627:therapeutic use; D013055:Spectrophotometry, Infrared
D000970:Antineoplastic Agents; D009607:Nitrosourea Compounds; D003543:Cysteamine; C048248:N'-(N-(2-chloroethyl)-N-nitroso)carbamoylcysteamine