CNC-半胱胺及相关化合物的合成与抗肿瘤活性

Synthesis and antineoplastic activity of CNC-cysteamine and related compounds.

作者信息

Tang W C, Schmid J, Fiebig H H, Eisenbrand G

出版信息

J Cancer Res Clin Oncol. 1986;111(1):25-30. doi: 10.1007/BF00402771.

DOI:10.1007/BF00402771

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12252979/

Abstract

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.

摘要

N'-[N-(2-氯乙基)-N-亚硝基]氨基甲酰半胱胺（CNC-半胱胺）及几种相关化合物已被合成，并在小鼠体内针对L 1210白血病进行了测试。N-(2-氯乙基)-N-亚硝基氨基甲酰叠氮化物（CNC-叠氮化物）与半胱胺反应生成了CNC-半胱胺和双(CNC)胱胺。在三乙胺存在下，CNC-叠氮化物与胱胺反应生成双(CNC)胱胺。出乎意料的是，还观察到生成了少量反应产物CNC-胱胺羧基叠氮化物。2-氯乙基异氰酸酯与半胱胺反应生成N-(2-氯乙基)氨基甲酰半胱胺2-氯乙基氨基甲酸酯。该半胱胺N,S-二氨基甲酰衍生物的亚硝化反应导致形成两种二亚硝基异构体的混合物。对新合成的CNC衍生物在小鼠体内针对L 1210白血病进行的初步测试表明，CNC-半胱胺、其二硫化物双(CNC)胱胺和CNC-胱胺羧基叠氮化物对L 1210白血病具有高度活性。

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本文引用的文献

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