Nitramino acids. Synthesis and biological evaluation of 1-nitroproline, 1-nitropipecolic acid, and N-nitrosarcosine.
The N-nitro derivatives of secondary alpha-amino acids, viz., 1-nitroproline (1a) (L and D), 1-nitro-DL-pipecolic acid (2a), and N-nitrosarcosine (3a), were prepared by the oxidation of the corresponding nitrosamino acids with peroxytrifluoroacetic acid. These nitramino acids (1a-3a) were not active against Escherichia coli, Candida albicans, Pseudomonas aeruginosa, or Mycobacterium smegmatis, and 1a and 2a did not show mutagenic activity in a Salmonella typhimurium TA-100 system, with or without added rat liver 9000g supernatant fraction. The marginal mutagenicity of 3a in this system suggests that additional work should be done to assess its carcinogenic-mutagenic potential.
D000818:Animals; D001419:Bacteria / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D066298:In Vitro Techniques; D007928:Lethal Dose 50; D008297:Male; D051379:Mice; D009153:Mutagens; D010875:Pipecolic Acids / Q000138:chemical synthesis* / Q000494:pharmacology; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D051381:Rats; D012521:Sarcosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
D009153:Mutagens; D010875:Pipecolic Acids; D011392:Proline; D012521:Sarcosine