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 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.
Süli-Vargha
H
H
Research Group for Peptide Chemistry, Hungarian Academy of Sciences, Budapest.
Bodi
J
J
Meszåros
M
M
Medzihradszky
K
K
D000970:Antineoplastic Agents / Q000032:analysis; D002330:Carmustine / Q000032:analysis; D055598:Chemical Phenomena; D002621:Chemistry; D002849:Chromatography, Gas; D009150:Mustard Compounds / Q000032:analysis / Q000138:chemical synthesis; D009607:Nitrosourea Compounds / Q000032:analysis / Q000138:chemical synthesis; D011392:Proline / Q000031:analogs & derivatives* / Q000032:analysis / Q000138:chemical synthesis; D013329:Structure-Activity Relationship; D014633:Valine / Q000031:analogs & derivatives* / Q000032:analysis / Q000138:chemical synthesis
D000970:Antineoplastic Agents; D009150:Mustard Compounds; D009607:Nitrosourea Compounds; C056701:N-(2-chloroethyl)-N-carbamoylprolinamide; C056702:N-(2-chloroethyl)-N-nitrosocarbamoylvalinamide; D011392:Proline; D014633:Valine; D002330:Carmustine