Isoquinolines. 6. Potential central nervous system antitumor agents. Nitrogen mustards of 3-amino-4-(p-aminophenyl)isoquinoline

J Med Chem. 1977 Nov;20(11):1504-8. doi: 10.1021/jm00221a030.

Abstract

A series of 3-amino-4-(p-aminophenyl)isoquinolines bearing the bis(2-chloroethyl)amino group was synthesized as potential CNS antitumor agents. Diol precursors 1e and 1f were prepared by the treatment of 1b and 1c with ethylene oxide. Diol precursors 5a-c and 9 were prepared by the treatment of 4a-c and 8 with diethanolamine. The reaction of these diols with SOCl2 yielded target mustards 10-15 which were evaluated in the intraperitoneal murine L1210 tumor. No intermediates or target mustards were active in this tumor system.

Publication types

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

MeSH terms

  • Alkylating Agents / chemical synthesis*
  • Alkylating Agents / therapeutic use
  • Animals
  • Blood-Brain Barrier*
  • Isoquinolines / chemical synthesis*
  • Isoquinolines / therapeutic use
  • Leukemia L1210 / drug therapy
  • Mice
  • Nitrogen Mustard Compounds / chemical synthesis*
  • Nitrogen Mustard Compounds / therapeutic use

Substances

  • Alkylating Agents
  • Isoquinolines
  • Nitrogen Mustard Compounds