9-Amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinoline Monohydrochloride Monohydrate(NIK-247)推定代謝物の合成(第2報)ジオール性代謝物

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The two dihydroxylated 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 the tricyclic diketone, 9-amino-2,3,6,7-tetrahydro-1H-cyclopenta [b] quinoline-1,8 (5H)-dione, with equivalent molar of NaBH_4,afforded the racemic two alcohols, (±)-9-amino-2,3,5,6,7,8-hexahydro-8-hydroxy-1H-cyclopenta [b] quinolin-1-one and (±)-9-amino-2,3,5,6,7,8-hexahydro-1-hydroxy-1H-cyclopenta [b] quinolin-8-one. (+)-9-Amino-2,3,5,6,7,8-hexahydro-8-hydroxy-1H-cyclopenta [b] quinolin-1-one was obtained by optical resolution of the corresponding racemic hydroxyketone using (-)-di-p-toluoyl-L-tartaric acid. The optically active dihydroxylated metabolites were obtained by reduction of the (+)-8-hydroxy-1-one with NaBH_4.
社団法人日本薬学会の論文
1995-12-25