57987-77-6

Usage

InChI:InChI=1/C9H9Cl2N.ClH/c10-8-2-1-6-3-4-12-5-7(6)9(8)11;/h1-2,12H,3-5H2;1H

Upstream product

• 74819-76-4 2-(2,3,-dichlorobenzylamino) 1-ethanol hydrochloride 
• 61563-36-8 7,8-dichloroisoquinoline 
• 6334-18-5 2,3-dichlorobenzylaldehyde 
• 73261-79-7 N-(2,3-dichlorobenzyl)-N-(2,2-dimethoxyethyl)acetamide 
• 73261-85-5 2-acetyl-7,8-dichloro-1,2-dihydroisoquinoline 
• 57987-75-4 N-<(2,3-dichlorophenyl)methylene>-2,2-dimethoxyethanamine 
• 57987-75-4 2,3-dichloro-N-(2,2-dimethoxyethyl)benzylidenamine 
• 61563-24-4 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline 
• 61563-45-9 2-acetyl-7,8-dichloro-1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 79-07-2 Chloroacetamide 

Relevant academic research and scientific papers

Method for preparing tetrahydroisoquinolines

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°.

Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis: I. Chloro-substituted 1,2,3,4-tetrahydroisoquinolines

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.

INTRAMOLECULAR FRIEDEL-CRAFTS ALKYLATIONS. II. AN EFFICIENT SYNTHESIS OF BIOLOGICALLY ACTIVE 1,2,3,4-TETRAHYDROISOQUINOLINES

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.

Method for preparing 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline

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.

7 AND 8-Halo substituted 1,2,3,4-tetrahydroisoquinoline compounds

1,2,3,4-Tetrahydroisoquinoline compounds having 7 and 8 halo substituents are inhibitors of phenylethanolamine N-methyltransferase.

Pharmaceutical compositions and methods of inhibiting phenylethanolamine N-methyltransferase

Pharmaceutical compositions and methods of inhibiting phenylethanolamine N-methyltransferase using 7 and/or 8 substituted 1,2,3,4-tetrahydroisoquinoline compounds.