[Synthesis of estimated metabolites of 9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinoline monohydrochloride monohydrate (NIK-247). I. Synthesis of mono-hydroxylated metabolites]

Yakugaku Zasshi. 1995 Dec;115(12):1016-21. doi: 10.1248/yakushi1947.115.12_1016.
[Article in Japanese]

Abstract

The two mono-hydroxylated metabolites of 9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinoline monohydrochloride monohydrate (NIK-247), which is a new drug for the treatment of dementia, were synthesized to determine their chemical structures. Reduction of two tricyclic ketones, 9-amino-1,2,3,5,6,7-hexahydro-8H-cyclopenta[b]quinolin-8-one and 9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]-quinolin-1-one, with NaBH4 afforded the corresponding racemic alcohols. The optically active mono-hydroxylated metabolites, (+)-9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-8-ol and (+)-9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-1-ol, were obtained by optical resolution of each racemic alcohol using (+)-di-p-toluoyl-D-tartaric acid.

Publication types

  • English Abstract

MeSH terms

  • Aminoquinolines / chemical synthesis*
  • Aminoquinolines / chemistry
  • Cholinesterase Inhibitors*
  • Psychotropic Drugs / chemical synthesis*
  • Psychotropic Drugs / chemistry

Substances

  • Aminoquinolines
  • Cholinesterase Inhibitors
  • Psychotropic Drugs
  • amiridine