350014-18-5

Basic information

• Product Name: Methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate
• Synonyms: Methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate;1,2,3,4-Tetrahydro-6-hydroxy-1-isoquinolinecarboxylic acid methyl ester
• CAS NO: 350014-18-5
• Molecular Formula: C₁₁H₁₃NO₃
• Molecular Weight: 207.22582
• Mol File: 350014-18-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 370℃
• Flash Point: 177℃
• Appearance: /
• Density: 1.231
• PKA: 9.70±0.40(Predicted)
• CAS DataBase Reference: Methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate(350014-18-5)
• EPA Substance Registry System: Methyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate(350014-18-5)

Safety Data

• Hazardous Substances Data: 350014-18-5(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 91523-50-1 rac-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid 
• 588-05-6 m-tyramine 
• 1700-37-4 3-Benzyloxybenzaldehyde 
• 24550-32-1 1-(benzyloxy)-3-[(E)-2-nitroethenyl]benzene 
• 100-83-4 meta-hydroxybenzaldehyde 
• 75-36-5 acetyl chloride 
• 38449-59-1 2-(3-hydroxyphenyl)ethylamine hydrobromide 
• 298-12-4 Glyoxilic acid 
• 2039-67-0 2-(3-methoxyphenyl)-1-ethanamine 

Downstream Products

• 350014-19-6 methyl N-(tert-butyloxycarbonyl)-6-hydroxy-3,4-dihydro-1H-isoquinoline-1-carboxylate 
• 362492-00-0 2-(tert-butoxycarbonyl)-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid 
• 350014-20-9 3,4-Dihydro-6-(phenylmethoxy)-1,2(1H)-isoquinolinedicarboxylic acid 1-methyl 2-(1,1-dimethylethyl) ester 
• 373638-25-6 6-benzyloxy-3,4-dihydro-1H-isoquinoline-1,2-dicarboxylic acid 2-tert-butyl ester 
• 373638-29-0 6-benzyloxy-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid (2-diisopropylamino-ethyl)-amide 
• 373637-06-0 1-(2-diisopropylamino-ethylcarbamoyl)-6-phenoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 373633-77-3 1-[[[2-[Bis(1-methylethyl)amino]ethyl]amino]carbonyl]-3,4-dihydro-6-(phenylmethoxy)-2(1H)-isoquinoline-carboxylic acid,1,1-dimethylethyl ester 

Relevant articles and documents

Synthesis of novel (benzimidazolyl)isoquinolinols and evaluation as adenosine A1 receptor tools

G protein-coupled receptors (GPCRs) constitute the largest family of transmembrane receptors in eukaryotes. The adenosine A1 receptor (A1AR) is a class A GPCR that is of interest as a therapeutic target particularly in the treatment of cardiovascular disease and neuropathic pain. Increased knowledge of the role A1AR plays in mediating these pathophysiological processes will help realise the therapeutic potential of this receptor. There is a lack of enabling tools such as selective fluorescent probes to study A1AR, therefore we designed a series of (benzimidazolyl)isoquinolinols conjugated to a fluorescent dye (31-35, 42-43). An improved procedure for the synthesis of isoquinolinols from tetrahydroisoquinolinols via oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and atmospheric oxygen is reported. This synthetic method offers advantages over previous metal-based methods for the preparation of isoquinolinols and isoquinolines, which are important scaffolds found in many biologically active compounds and natural products. We report the first synthesis of the (benzimidazolyl)isoquinolinol compound class, however the fluorescent conjugates were not successful as A1AR fluorescent ligands.

Tetrahydroisoquinoline based sulfonamide hydroxamates as potent matrix metalloproteinase inhibitors

The synthesis and MMP inhibitory activity of a series of tetrahydroisoquinoline based sulfonamide hydroxamates are described. In nine MMPs tested, most of the compounds display potent inhibition activity except for MMP-7. Some subtle isozyme selectivity is observed by varying the substituents at the 6- and 7-positions and aromatic ring of arylsulfonyl groups.

Lactam derivatives as antiarrhythmic agents

Lactam derivatives of the formula where X is —C(═O)NR3′—, —NR3′C(═O)—, —C(═NCN)NR3′—, —NR3′C(═NCN)—, —CH2NR3′—, —CH(alkyl)NR3′—, —CH(COOalkyl)NR3′—, —CH(CH2