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Literature DB >> 3949847

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

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

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.

Entities: Chemical Disease Species

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Year: 1986 PMID： 3949847 DOI： 10.1007/bf00402771

Source DB: PubMed Journal: J Cancer Res Clin Oncol ISSN： 0171-5216 Impact factor: 4.553

9 in total

1. Synthesis of steroidal nitrosoureas with antitumor activity.

Authors: H Y Lam; A Begleiter; G J Goldenberg; C M Wong
Journal: J Med Chem Date: 1979-02 Impact factor: 7.446

2. Phase II evaluation of chlorozotocin (NSC-178248) in advanced human cancer.

Authors: R W Talley; M K Samson; R W Brownlee; A M Samhouri; R J Fraile; L H Baker
Journal: Eur J Cancer Date: 1981-03 Impact factor: 9.162

3. The synthesis of potential anticancer agents. XXXVI. N-nitrosoureas. II. Haloalkyl derivatives.

Authors: T P Johnston; G S McCaleb; P S Opliger; J A Montgomery
Journal: J Med Chem Date: 1966-11 Impact factor: 7.446

4. Biochemical and cytotoxic properties of the isomeric forms of N,N'-bis[N-2-chloroethyl)-N-nitrosocarbamoyl] cystamine.

Authors: J J Farhi; M Bennoun; H Tapiero; A L Wang; K D Tew
Journal: Biochem Pharmacol Date: 1984-08-15 Impact factor: 5.858

1 in total

1. Antineoplastic efficacy of melphalan and N-(2-chloroethyl)-N-nitrosocarbamoyl-omega-lysine, in combination with diazoxide or insulin in autochthonous mammary carcinoma of the Sprague-Dawley rat.

Authors: T Klenner; M R Berger; O Zelezny; M Fink; D Schmähl
Journal: J Cancer Res Clin Oncol Date: 1990 Impact factor: 4.553

1 in total

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

1. Synthesis of steroidal nitrosoureas with antitumor activity.

2. Phase II evaluation of chlorozotocin (NSC-178248) in advanced human cancer.

3. The synthesis of potential anticancer agents. XXXVI. N-nitrosoureas. II. Haloalkyl derivatives.

4. Biochemical and cytotoxic properties of the isomeric forms of N,N'-bis[N-2-chloroethyl)-N-nitrosocarbamoyl] cystamine.

5. Activated N-nitrosocarbamates for regioselective synthesis of N-nitrosoureas.

6. Cytostatic activity of steroid linked nitrosoureas.

7. Metabolic disposition of 2-chloroethyl nitrosocarbamoylcystamine in rats.

8. Effect of 1-(2-chloroethyl)-3-isobutyl-3-(beta-maltosyl)-1-nitrosourea on experimental tumors.

9. Studies on synthesis and anticancer activity of selected N-(2-fluoroethyl)-N-nitrosoureas.

1. Antineoplastic efficacy of melphalan and N-(2-chloroethyl)-N-nitrosocarbamoyl-omega-lysine, in combination with diazoxide or insulin in autochthonous mammary carcinoma of the Sprague-Dawley rat.