Decomposition of N-(2-chloroethyl)-N-nitrosocarbamoyl amino acid amides

The chemical decomposition of N-(2-chloroethyl)-N-nitrosocarbamoyl (Q(NO] prolinamide and valinamide were studied under physiological conditions. The volatile products were identified with GC. Q(NO)-Pro-NH2 gave twice the amount of ethylene glycol and only one-fifth of the 2-chloroethanol produced b...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1988-08, Vol.31 (8), p.1492-1495
Main Authors: Suli-Vargha, Helga, Bodi, Jozsef, Meszaros, Miomir, Medzihradszky, Kalman
Format: Article
Language:English
Subjects:
Antineoplastic Agents - analysis
Carmustine - analysis
Chemical Phenomena
Chemistry
Chromatography, Gas
Mustard Compounds - analysis
Mustard Compounds - chemical synthesis
Nitrosourea Compounds - analysis
Nitrosourea Compounds - chemical synthesis
Proline - analogs & derivatives
Proline - analysis
Proline - chemical synthesis
Structure-Activity Relationship
Valine - analogs & derivatives
Valine - analysis
Valine - chemical synthesis
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Summary:The chemical decomposition of N-(2-chloroethyl)-N-nitrosocarbamoyl (Q(NO] prolinamide and valinamide were studied under physiological conditions. The volatile products were identified with GC. Q(NO)-Pro-NH2 gave twice the amount of ethylene glycol and only one-fifth of the 2-chloroethanol produced by Q(NO)-Val-NH2 or BCNU, pointing to different pathways of their decomposition. The carbamoylating activity was also investigated in the presence of cyclohexylamine, and it was found to lead mainly to intramolecular carbamoylation with the formation of hydantoin derivatives.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00403a003