147497-32-3

Basic information

• Product Name: 6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE
• Synonyms: 6-bromo-3,4-dihydroisoquinolin-1(2H)-one;6-BROMO-3,4-1(1H)-ISOQUINOLINONE;6-BROMO-3,4-DIHYDRO-1(1H)-ISOQUINOLINONE;6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ON;1(2H)-Isoquinolinone, 6-bromo-3,4-dihydro-;6-Bromo-3,4-dihydro-1(2H)-isoquinolinone;6-BroMo-1-oxo-1,2,3,4-tetrahydroisoquinoline;6-broMo-1,2,3,4-tetrahydroisoquinolin-1-one
• CAS NO: 147497-32-3
• Molecular Formula: C₉H₈BrNO
• Molecular Weight: 226.07
• Product Categories: Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 147497-32-3.mol
• Article Data: 36

Chemical Properties

• Melting Point: 170.0-173.1 °C
• Boiling Point: 453.294 °C at 760 mmHg
• Flash Point: 227.944 °C
• Appearance: /
• Density: 1.559 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.22±0.20(Predicted)
• CAS DataBase Reference: 6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE(147497-32-3)
• EPA Substance Registry System: 6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE(147497-32-3)

Safety Data

• Hazardous Substances Data: 147497-32-3(Hazardous Substances Data)

Usage

Description

6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceutical compounds. It is characterized by its unique chemical structure, which includes a bromo group at the 6th position, a 3,4-dihydroisoquinolinone core, and a 2H-isoquinolinone ring. 6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE plays a significant role in the development of novel therapeutic agents targeting specific biological receptors.

Uses

Used in Pharmaceutical Industry:
6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE is used as an intermediate in the synthesis of benzolactams, which are known as dopamine D3 receptor ligands. These ligands are essential for developing drugs that can modulate the activity of the dopamine D3 receptor, potentially leading to treatments for various neurological and psychiatric disorders.
6-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE is also used as an intermediate in the synthesis of new, selective 3-aminopyrazole-based MK2 inhibitors. These inhibitors have been proven to inhibit intracellular phosphorylation of hsp27 as well as LPS-induced TNFα release in cells. MK2 inhibitors hold promise in the development of therapeutic agents for inflammatory diseases and other conditions where the MK2 pathway is implicated.

InChI:InChI=1/C9H8BrNO/c10-7-1-2-8-6(5-7)3-4-11-9(8)12/h1-2,5H,3-4H2,(H,11,12)

Upstream product

• 58971-11-2 2-(3-bromophenyl)ethanamine 
• 305447-65-8 methyl 4-(bromophen)ethylcarbamate 
• 1279816-33-9 methyl 3-bromophenethylcarbamate 
• 75-75-2 methanesulfonic acid 
• 34598-49-7 5-Bromo-1-indanone 
• 7732-18-5 water 

Downstream Products

• 735351-82-3 2-benzyl-6-bromo-3,4-dihydroisoquinolin-1(2H)-one 
• 959755-58-9 (4-morpholin-4-yl-phenyl)-[5-(1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]-carbamic acid tert-butyl ester 
• 1214900-33-0 tert-butyl 6-bromo-1-oxo-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 1131223-44-3 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinolin-1-one 
• 1219825-26-9 2-cyclopropyl-(6-N-diphenylmethyleneamino)-3,4-dihydroisoquinolin-1(2H)-one 
• 1178884-83-7 acetic acid 2-(6-cyclopropyl-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl ester 
• 1178884-67-7 2-(3-bromo-2-hydroxymethyl-phenyl)-6-cyclopropyl-3,4-dihydro-2H-isoquinolin-1-one 

Relevant articles and documents

New Series of Potent Allosteric Inhibitors of Deoxyhypusine Synthase

Deoxyhypusine synthase (DHPS) is the primary enzyme responsible for the hypusine modification and, thereby, activation of the eukaryotic translation initiation factor 5A (eIF5A), which is key in regulating the protein translation processes associated with tumor proliferation. Although DHPS inhibitors could be a promising therapeutic option for treating cancer, only a few studies reported druglike compounds with this inhibition property. Thus, in this work, we designed and synthesized a new chemical series possessing fused ring scaffolds designed from high-throughput screening hit compounds, discovering a 5,6-dihydrothieno[2,3-c]pyridine derivative (26d) with potent inhibitory activity; furthermore, the X-ray crystallographic analysis of the DHPS complex with 26d demonstrated a distinct allosteric binding mode compared to a previously reported inhibitor. These findings could be significantly useful in the functional analysis of conformational changes in DHPS as well as the structure-based design of allosteric inhibitors.

Metal-Free Synthesis of Polycyclic Quinazolinones Enabled by a (NH4)2S2O8-Promoted Intramolecular Oxidative Cyclization

An efficient metal-free, (NH4)2S2O8 mediated intramolecular oxidative cyclization for the construction of polycyclic heterocycles was disclosed. A series of polycyclic quinazolinone derivatives with good functional group tolerance were obtained in high yields. The natural products tryptanthrin and rutaecarpine, as well as their derivatives, were easily synthesized by this strategy. A preliminary mechanism study suggested the carbon-centered radical was involved in the catalytic cycle.

BENZAZEPINE DERIVATIVES

The present invention provides novel benzazepine compounds of Formula (1), or salts thereof, having vasopressin V1a and V2 antagonisms, and medical uses thereof. In the formula, R1 is optionally substituted C1-6 alkyl, etc.; L is -C(=O)-NH-, etc.; Ring A1 is a hydrocarbon ring, etc.; Ring A2 is a hydrocarbon ring, etc.; and each of Rings A1 and A2 may have at least one substituent.