cis-4-[[[(2-Chloroethyl)nitrosoamino]carbonyl]methylamino] cyclohexanecarboxylic acid, a nitrosourea with latent activity against an experimental solid tumor

J Med Chem. 1984 Jan;27(1):97-9. doi: 10.1021/jm00367a022.

Abstract

cis-4-[[[(2-Chloroethyl)nitrosoamino]carbonyl]methylamino] cyclohexanecarboxylic acid (N-Me-cis-CCCNU) was synthesized in five steps from cis-4-aminocyclohexanecarboxylic acid via an N-tosylated intermediate. N-Me-cis-CCCNU, which is incapable of the facile decomposition that characterizes the clinically useful nitrosoureas, effected a significant cure rate of both early and established murine Lewis lung carcinoma, even though its in vitro half-life was approximately 5.5 times that of the unmethylated parent compound. This is the first observation of latent activity of a nitrosourea against an experimental solid tumor.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Drug Evaluation, Preclinical
  • Half-Life
  • Indicators and Reagents
  • Lomustine / analogs & derivatives*
  • Lomustine / chemical synthesis
  • Lomustine / therapeutic use
  • Lomustine / toxicity
  • Lung Neoplasms / drug therapy
  • Mice
  • Semustine / therapeutic use
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Indicators and Reagents
  • Semustine
  • Lomustine
  • 4-((((2-chloroethyl)nitrosoamino)carbonyl)methylamino)cyclohexanecarboxylic acid