Serotonin 5-HT_4 Receptor Agonistic Activity of the Optical Isomers of (±)-4-Amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2,3-dihydro-2-methylbenzo[b]furan-7-carboxamide

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概要

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• The enantiomers, (R)-(-)-1 and (S)-(+)-1,of (±)-4-amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2,3-dihydro-2-methylbenzo[b]furan-7-carboxamide [(±)-1] were prepared from optically active benzyl 4-acetylamino-2,3-dihydro-2-methylbenzo[b]furan-7-carboxylate[(R)-(+)-6,(S)-(-)-6], respectively. The requisite (R)-(+)-6 and (S)-(-)-6 were prepared by large-scale preparative HPLC on chiral stationary phases (CSPs). The absolute configuration of (S)-(+)-1 was determined by single crystal X-ray analysis. The serotonin 5-HT_4 receptor agonistic activity of (S)-(-)-1 hemifumarate (SK-951) which was hemifumarate of (S)-(+)-1 was about twice that of the other enantiomer (R)-(+)-1 hemifumarate which was hemifumarate of (R)-(-)-1.

• 公益社団法人日本薬学会の論文
• 1998-06-15

著者

• KATAOKA Tadashi

  Gifu Pharmaceutical University

• Taga T

  Kyoto Univ. Kyoto Jpn

• KAKIGAMI Takuji

  General Research Park, Sanwa Kagaku Kenkyusho Co., Ltd.,

• USUI Toshinao

  General Research Park, Sanwa Kagaku Kenkyusho Co., Ltd.,

• IKAMI Takao

  General Research Park, Sanwa Kagaku Kenkyusho Co., Ltd.,

• TSUKAMOTO Katsura

  General Research Park, Sanwa Kagaku Kenkyusho Co., Ltd.,

• MIWA Yoshihisa

  Faculty of Pharmaceutical Sciences, Kyoto University

• TAGA Tooru

  Faculty of Pharmaceutical Sciences, Kyoto University

• Taga Tooru

  Faculty Of Pharmaceutical Science Kyoto University

• Miwa Yoshihisa

  Faculty Of Pharmaceutical Sciences Kyoto University

• Ito T

  Tottori Univ. Tottori Jpn

• Usui Toshinao

  Drug Discovery Research Department Sanwa Kagaku Kenkyusho Co. Ltd.

• Kakigami Takuji

  General Research Park Sanwa Kagaku Kenkyusho Co. Ltd.

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