δオピオイド受容体作動薬, TAN-67の設計合成 Rational Drug Design of δ Opioid Receptor Agonist TAN-67

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A selective nonpeptidic δ opioid receptor agonist TAN-67, (4a<I>S</I><SUP>*</SUP>, 12 a<I>R</I><SUP>*</SUP>) -4 a- (3-hydroxyphenyl) -2-methyl-1, 2, 3, 4, 4 a, 5, 12, 12 a-octahydropyrido [3, 4-<I>b</I>] acridine was designed from the selective δ opioid receptor antagonist NTI on the basis of the message-address concept and the accessory site theory. (-) -TAN-67 is a potent and selective δ<SUB>1</SUB> opioid receptor agonist and showed profound antinociceptive effect, cardioprotective effect, and antiarrhythmic effect. On the contrary, (+) -TAN-67 induced hyperalgesia, which is the opposite effect of the antinociception. Optical resolution of racemic TAN-67 and the synthesis of (4a<I>S</I><SUP>*</SUP>, 8 a<I>R</I><SUP>*</SUP>) -4 a- (3-methoxyphenyl) -2-methyl-6-oxodecahydroisoquinoline, the important intermediate ketone of TAN-67 synthesis were also described.

収録刊行物

  • 有機合成化学協会誌 : JOURNAL OF Synthetic Organic Chemistry JAPAN  

    有機合成化学協会誌 : JOURNAL OF Synthetic Organic Chemistry JAPAN 64(4), 371-381, 2006-04-01 

    The Society of Synthetic Organic Chemistry, Japan

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各種コード

  • NII論文ID(NAID)
    10018131602
  • NII書誌ID(NCID)
    AN0024521X
  • 本文言語コード
    JPN
  • 資料種別
    ART
  • ISSN
    00379980
  • NDL 記事登録ID
    7921747
  • NDL 雑誌分類
    ZP11(科学技術--化学・化学工業--有機化学・有機化学工業)
  • NDL 請求記号
    Z17-256
  • データ提供元
    CJP書誌  NDL  J-STAGE 
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