22245-95-0

Basic information

• Product Name: 7-CHLORO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE
• Synonyms: 7-CHLORO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE;7-chloro-3,4-dihydroisoquinolin-1(2H)-one;7-chloro-3,4-dihydro-1(2h)-isoquinolinone;7-chloro-3,4-dihydroisoquinolin-1-ol;1(2H)-Isoquinolinone,7-chloro-3,4-dihydro-;7-chloro-3,4-dihydroisoquinolin-1-one
• CAS NO: 22245-95-0
• Molecular Formula: C₉H₈ClNO
• Molecular Weight: 181.62
• Mol File: 22245-95-0.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 7-CHLORO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-CHLORO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE(22245-95-0)
• EPA Substance Registry System: 7-CHLORO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE(22245-95-0)

Safety Data

• Hazardous Substances Data: 22245-95-0(Hazardous Substances Data)

Usage

General Description

7-CHLORO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE is a chemical compound that belongs to the class of isoquinolin-1-one derivatives. It is a chlorinated derivative of 2H-isoquinolin-1-one and has a dihydro-3,4-dihydroxy structure. 7-CHLORO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE has potential pharmaceutical applications due to its structural features, such as its isoquinoline ring system and chloro substituent, which may contribute to its biological activities. 7-CHLORO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE may be used in medicinal chemistry research for the development of new drugs and therapeutic agents.

Upstream product

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• 55121-08-9 1-chloro-3-(2-isocyanatoethyl)benzene 

Downstream Products

• 104576-30-9 1-phenyl-7-chloro-3,4-dihydroisoquinoline 
• 82771-60-6 7-chloro-1,2,3,4-tetrahydro-isoquinoline 
• 439116-79-7 tert-butyl 2-[4-chloro-2-(hydroxymethyl)phenyl]-ethylcarbamate 
• 1231892-74-2 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinolin-1(2H)-one 
• 439116-80-0 2-(2-(tert-butoxycarbonylamino)ethyl)-5-chlorobenzyl azide 
• 439116-12-8 tert-butyl 2-[2-(aminomethyl)-4-chlorophenyl]ethylcarbamate 

Relevant articles and documents

Intramolecular Reductive Cyclization of o-Nitroarenes via Biradical Recombination

A visible-light-induced/thiourea-mediated intramolecular cyclization of o-nitroarenes under mild conditions is realized for the first time, which provides an efficient and environmentally friendly way to access pharmaceutical relevant quinazolinone derivatives. The reaction can be easily extended to gram level by using a continuous-flow setup with high efficiency. Mechanistic investigation including control experiments, transient fluorescence, UV-vis spectra, and DFT calculations suggests that the formation of active biradical intermediates via intramolecular single electron transfer (SET) is key stage in the catalytic cycle.

Catalyst-free cyclization of anthranils and cyclic amines: One-step synthesis of rutaecarpine

An efficient synthesis of a variety of quinazolinone derivatives via a direct cyclization reaction between commercially available anthranils and cyclic amines is described. The developed transformation proceeds with the merits of high step- and atom-efficiency, a broad substrate scope, and good to excellent yields, without additional catalysts, and offers a practical way for the preparation of rutaecarpine and its derivatives with structural diversity.

Fragment-Based Discovery of a Potent, Orally Bioavailable Inhibitor That Modulates the Phosphorylation and Catalytic Activity of ERK1/2

Aberrant activation of the MAPK pathway drives cell proliferation in multiple cancers. Inhibitors of BRAF and MEK kinases are approved for the treatment of BRAF mutant melanoma, but resistance frequently emerges, often mediated by increased signaling through ERK1/2. Here, we describe the fragment-based generation of ERK1/2 inhibitors that block catalytic phosphorylation of downstream substrates such as RSK but also modulate phosphorylation of ERK1/2 by MEK without directly inhibiting MEK. X-ray crystallographic and biophysical fragment screening followed by structure-guided optimization and growth from the hinge into a pocket proximal to the C-α helix afforded highly potent ERK1/2 inhibitors with excellent kinome selectivity. In BRAF mutant cells, the lead compound suppresses pRSK and pERK levels and inhibits proliferation at low nanomolar concentrations. The lead exhibits tumor regression upon oral dosing in BRAF mutant xenograft models, providing a promising basis for further optimization toward clinical pERK1/2 modulating ERK1/2 inhibitors.