δオピオイド受容体作動薬, TAN-67の設計合成 [in Japanese] Rational Drug Design of δ Opioid Receptor Agonist TAN-67 [in Japanese]
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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.
- J. Synth. Org. Chem. Jpn.
J. Synth. Org. Chem. Jpn. 64(4), 371-381, 2006-04-01
The Society of Synthetic Organic Chemistry, Japan