δオピオイド受容体作動薬，ＴＡＮ‐６７の設計合成

• 長瀬 博

  北里大学薬学部生命薬化学教室

• 藤井 秀明

  東レ株式会社医薬研究所

書誌事項

タイトル別名

• Rational Drug Design of .DELTA. Opioid Receptor Agonist TAN-67
• デルタ オピオイド ジュヨウタイ サドウヤク TAN 67 ノ セッケイ ゴウセイ

抄録

A selective nonpeptidic δ opioid receptor agonist TAN-67, (4aS^*, 12 aR^*) -4 a- (3-hydroxyphenyl) -2-methyl-1, 2, 3, 4, 4 a, 5, 12, 12 a-octahydropyrido [3, 4-b] 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 δ₁ 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 (4aS^*, 8 aR^*) -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

  有機合成化学協会誌 64 (4), 371-381, 2006

  公益社団法人 有機合成化学協会

キーワード

• opioid
• δ agonist
• κ agonist
• μ agonist
• analgesics
• dependence
• TAN-67
• hyperalgesia
• morphine

詳細情報

• CRID: 1390001205311038848
• NII論文ID: 10018131602
• NII書誌ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.64.371
• ISSN: 18836526
• ISSN: 00379980
• NDL書誌ID: 7921747
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I7921747
• 本文言語コード: ja
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可