title: [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].
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.
authors.affiliation: Omiya Research Laboratory, Nikken Chemicals Co., Ltd., Saitama, Japan.
authors.forename: T
authors.initials: T
authors.lastname: Komatsu
authors.forename: M
authors.initials: M
authors.lastname: Yano
authors.forename: H
authors.initials: H
authors.lastname: Inada
authors.forename: M
authors.initials: M
authors.lastname: Iwamoto
authors.forename: K
authors.initials: K
authors.lastname: Okada
authors.forename: K
authors.initials: K
authors.lastname: Suzuki
mesh_terms: D000634:Aminoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D002800:Cholinesterase Inhibitors; D011619:Psychotropic Drugs / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000634:Aminoquinolines; D002800:Cholinesterase Inhibitors; D011619:Psychotropic Drugs; C049860:amiridine