Rational Drug Design of .DELTA. Opioid Receptor Agonist TAN-67
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- Nagase Hiroshi
- Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Kitasato University
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- Fujii Hideaki
- 東レ株式会社医薬研究所
Bibliographic Information
- Other Title
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- δオピオイド受容体作動薬,TAN‐67の設計合成
- 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
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Abstract
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.
Journal
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- Journal of Synthetic Organic Chemistry, Japan
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Journal of Synthetic Organic Chemistry, Japan 64 (4), 371-381, 2006
The Society of Synthetic Organic Chemistry, Japan
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Details
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- CRID
- 1390001205311038848
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- NII Article ID
- 10018131602
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- NII Book ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL BIB ID
- 7921747
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- Text Lang
- ja
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- Abstract License Flag
- Disallowed