Summary
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.
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Dedicated to Professor Dietrich Schmähl on the occasion of his 60th birthday
This work was supported in part by the German Ministry for Research and Technology (BMFT)
Visiting Professor from People's Republic of China
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Tang, Wc., Schmid, J., Fiebig, HH. et al. Synthesis and antineoplastic activity of CNC-cysteamine and related compounds. J Cancer Res Clin Oncol 111, 25–30 (1986). https://doi.org/10.1007/BF00402771
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DOI: https://doi.org/10.1007/BF00402771