- Method for preparing tetrahydroisoquinolines
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A method for preparing 1,2,3,4-tetrahydroisoquinolines comprising heating N-halo or hydroxyethyl-N-benzylamines in an aluminum chloride melt at 160°-210°.
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- Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis: I. Chloro-substituted 1,2,3,4-tetrahydroisoquinolines
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In a search for inhibitors of epinephrine biosynthesis as potential therapeutic agents, a series of 13 ring-chlorinated 1,2,3,4-tetrahydroisoquinolines was prepared. These compounds were tested initially for their ability to inhibit rabbit adrenal phenylethanolamine N-methyltransferase (PNMT) in vitro. Enzyme-inhibitor dissociation constants, determined for the six most potent members of the series, indicated the following order of decreasing potency: 7,8-Cl2>6,7,8-Cl3>7-Cl~8-Cl>5,6,7,8-Cl4>5,7,8-Cl3. These compounds were subsequently examined for PNMT-inhibiting activity in intact rats and mice. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline (SK&F 64139) was the most potent member of the series both in vitro and in vivo and is currently undergoing clinical investigation.
- Bondinell,Chapin,Girard,Kaiser,Krog,Pavloff,Schwartz,Silvestri,Vaidya,Lam,Wellman,Pendleton
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p. 506 - 511
(2007/10/02)
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- INTRAMOLECULAR FRIEDEL-CRAFTS ALKYLATIONS. II. AN EFFICIENT SYNTHESIS OF BIOLOGICALLY ACTIVE 1,2,3,4-TETRAHYDROISOQUINOLINES
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A new synthesis of tetrahydroisoquinolines bearing electron withdrawing groups is presented.The scope and mechanism of the reaction are discussed.Many of these tetrahydroisoquinolines are potent inhibitors of the enzyme PNMT.
- Mendelson, W. L.,Spainhour, C. B.,Jones, S. S.,Lam, B. L.,Wert, K. L.
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p. 1393 - 1396
(2007/10/02)
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- Method for preparing 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline
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A novel process for preparing 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline by cyclizing N-acetyl-2,3-dichlorobenzylaminoacetaldehyde dimethyl acetal with a Lewis acid, reducing, and hydrolyzing the resulting acylated isoquinoline is disclosed.
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- 7 AND 8-Halo substituted 1,2,3,4-tetrahydroisoquinoline compounds
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1,2,3,4-Tetrahydroisoquinoline compounds having 7 and 8 halo substituents are inhibitors of phenylethanolamine N-methyltransferase.
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- Pharmaceutical compositions and methods of inhibiting phenylethanolamine N-methyltransferase
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Pharmaceutical compositions and methods of inhibiting phenylethanolamine N-methyltransferase using 7 and/or 8 substituted 1,2,3,4-tetrahydroisoquinoline compounds.
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