102877-50-9

Basic information

• Product Name: 1,2,3,4-TETRAHYDRO-ISOQUINOLIN-5-OL
• Synonyms: 5-Hydroxy-1,2,3,4-tetrahydroisoquinoline;H90103;1,2,3,4-tetrahydro-5-Isoquinolinol;1,2,3,4-tetrahydro-5-hydroxy-isoquinoline
• CAS NO: 102877-50-9
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149.19
• EINECS: -0
• Mol File: 102877-50-9.mol

Chemical Properties

• Melting Point: 273 °C
• Boiling Point: 294.3 °C at 760 mmHg
• Flash Point: 153.6 °C
• Appearance: /
• Density: 1.141
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.582
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 9.30±0.20(Predicted)
• CAS DataBase Reference: 1,2,3,4-TETRAHYDRO-ISOQUINOLIN-5-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-TETRAHYDRO-ISOQUINOLIN-5-OL(102877-50-9)
• EPA Substance Registry System: 1,2,3,4-TETRAHYDRO-ISOQUINOLIN-5-OL(102877-50-9)

Safety Data

• Hazardous Substances Data: 102877-50-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,2,3,4-Tetrahydroisoquinolin-5-ol is used as a reagent for the preparation of potent and selective inhibitors of type 5 17-Beta-Hydroxysteroid dehydrogenase AKR1C3. This enzyme plays a crucial role in the metabolism of androgens and estrogens, and its inhibition can have therapeutic applications in the treatment of hormone-dependent diseases and cancers.

InChI:InChI=1/C9H11NO/c11-9-3-1-2-7-6-10-5-4-8(7)9/h1-3,10-11H,4-6H2

Upstream product

• 2439-04-5 5-hydroxyisoquinoline 
• 115955-90-3 1,2,3,4-tetrahydroisoquinolin-5-amine 
• 119-65-3 isoquinoline 
• 27655-40-9 isoquinoline-5-sulfonic acid 

Downstream Products

• 216064-48-1 2-tert-butyloxycarbonyl-5-hydroxy-1,2,3,4-tetrahydroisoquinoline 
• 1394241-51-0 C₁₆H₁₅NO₅S 
• 14097-42-8 5-Hydroxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 91133-00-5 2-Acetyl-5-hydroxy-1,2,3,4-tetrahydro-isochinolin 
• 56135-34-3 5-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinoline 
• 441065-33-4 5-formyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 853076-94-5 5-[2-(2-biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethoxy]-8-(2-methoxycarbonyl-ethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid propyl ester 
• 853076-92-3 5-[2-(2-biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethoxy]-8-(2-methoxycarbonyl-ethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 918411-15-1 8-(2-methoxycarbonyl-ethyl)-5-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid prop-2-ynyl ester 
• 918411-14-0 8-(2-methoxycarbonyl-ethyl)-5-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid propyl ester 
• 918411-16-2 8-(2-methoxycarbonyl-ethyl)-5-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid isobutyl ester 
• 853076-93-4 3-{5-[2-(2-biphenyl-4-yl-5-methyl-oxazol-4-yl)-ethoxy]-l,2,3,4-tetrahydro-isoquinolin-8-yl}-propionic acid methyl ester 

Relevant articles and documents

Potent P2Y1 urea antagonists bearing various cyclic amine scaffolds

A number of new amine scaffolds with good inhibitory activity in the ADP-induced platelet aggregation assay have been found to be potent antagonists of the P2Y1 receptor. SAR optimization led to the identification of isoindoline 3c and piperidine 4a which showed good in vitro binding and functional activities, as well as improved aqueous solubility. Among them, the piperidine 4a showed the best overall profile with favorable PK parameters.

Synthesis of substituted 5-aminomethyl tetrahydro-isoquinolines and dihydro-isoindoles

The synthesis of ten substituted aminomethylene tetrahydro-isoquinolines is described, proceeding in eight steps from 5-hydroxyisoquinoline via reductive amination of N-Boc tetrahydro-isoquinoline 5-carboxaldehyde. Likewise, reductive amination was used to prepare four substituted dihydro-isoindoles from the corresponding aldehyde. The dihydro-isoindole ring system was conveniently accessed via a 2+2+2 cycloaddition reaction.

PRMT5 INHIBITORS AND USES THEREOF

Described herein are compounds of Formula (I), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5-mediated disorders are also described.

Preparation method of tetrahydroisoquinoline derivative

The invention discloses a preparation method of a tetrahydroisoquinoline derivative which is N-Fmoc-1,2,3,4-tetrahydroisoquinoline-5-alcohol. The preparation method comprises the following steps: taking isoquinoline as a starting raw material, loading sulfonic acid groups, hydrolyzing, hydrogenating and carrying out Fmoc protection to obtain a target product. The compound is used as an important medical intermediate.

PRMT5 INHIBITORS CONTAINING A DIHYDRO- OR TETRAHYDROISOQUINOLINE AND USES THEREOF

Described herein are compounds of Formula (A), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5- mediated disorders are also described.

Tetrahydroisoquinoline PPARγ agonists: Design of novel, highly selective non-TZD antihyperglycemic agents

Novel tetrahydroisoquinolines have been developed as potent PPAR ligands. Evaluation of these compounds in PPARγ responsive models of type 2 diabetes is described.

HETEROCYCLIC COMPOUNDS AS MODULATORS OF PEROXISOME PROLIFERATOR ACTIVATED RECEPTORS, USEFUL FOR THE TREATMENT AND/OR PREVENTION OF DISORDERS MODULATED BY A PPAR

The present invention is directed to a compound of formula (I), or a pharmaceutically acceptable salt, solvate, hydrate or stereoisomer thereof, which is useful in treating or preventing disorders mediated by a peroxisome proliferator activated receptor (PPAR) such as syndrome X, type II diabetes, hyperglycemia, hyperlipidemia, obesity, coagaulopathy, hypertension, arteriosclerosis, and other disorders related to syndrome X and cardiovascular diseases.