4053-33-2

Basic information

• Product Name: 2(1H)-Quinolinone, 5-methyl-
• Synonyms: 5-Methyl-carbostyryl;5-Methyl-1H-quinolin-2-one;1,2-Dihydro-5-methylquinolin-2-one;5-Methylcarbostyril;5-methylquinolin-2(1H)-one
• CAS NO: 4053-33-2
• Molecular Formula: C10H9NO
• Molecular Weight: 159.188
• Mol File: 4053-33-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 221 - 223 °C
• CAS DataBase Reference: 2(1H)-Quinolinone, 5-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(1H)-Quinolinone, 5-methyl-(4053-33-2)
• EPA Substance Registry System: 2(1H)-Quinolinone, 5-methyl-(4053-33-2)

Safety Data

• Hazardous Substances Data: 4053-33-2(Hazardous Substances Data)

Usage

Structure

Bicyclic, derivative of quinolinone

Usage

Building block in the synthesis of pharmaceuticals and agrochemicals

Biological activity

Exhibits biological activity, studied for potential medicinal properties

Importance

Important intermediate in organic synthesis, widely used in the chemical industry.

Upstream product

• 7661-55-4 5-methylquinoline 
• 41085-43-2 2-bromo-3-nitrotoluene 
• 57830-64-5 3′-methylcinnamanilide 
• 23980-96-3 (E)-N-(3-methylphenyl)-3-ethoxypropenamide 
• 108-44-1 1-amino-3-methylbenzene 
• 4964-71-0 5-bromoquinoline 
• 4053-41-2 5-methylquinoline 1-oxide 

Relevant articles and documents

PRMT5 INHIBITOR COMPOUNDS

A series of PRMT5 inhibitor compounds are described. The compounds are useful as PRMT5 inhibitor compounds and in the treatment of PRMT5 mediated diseases, disorders, and symptoms thereof.

2-AMINOQUINOLINE-BASED COMPOUNDS FOR POTENT AND SELECTIVE NEURONAL NITRIC OXIDE SYNTHASE INHIBITION

Various 2-aminoquinoline compounds as can be used, in vivo or in vitro, for selective inhibition of neuronal nitric oxide synthase.

Creating novel activated factor XI inhibitors through fragment based lead generation and structure aided drug design

Activated factor XI (FXIa) inhibitors are anticipated to combine anticoagulant and profibrinolytic effects with a low bleeding risk. This motivated a structure aided fragment based lead generation campaign to create novel FXIa inhibitor leads. A virtual screen, based on docking experiments, was performed to generate a FXIa targeted fragment library for an NMR screen that resulted in the identification of fragments binding in the FXIa S1 binding pocket. The neutral 6-chloro-3,4-dihydro-1H-quinolin-2-one and the weakly basic quinolin-2-amine structures are novel FXIa P1 fragments. The expansion of these fragments towards the FXIa prime side binding sites was aided by solving the X-ray structures of reported FXIa inhibitors that we found to bind in the S1-S1'-S2' FXIa binding pockets. Combining the X-ray structure information from the identified S1 binding 6-chloro-3,4-dihydro-1H-quinolin-2-one fragment and the S1-S1'-S2' binding reference compounds enabled structure guided linking and expansion work to achieve one of the most potent and selective FXIa inhibitors reported to date, compound 13, with a FXIa IC50 of 1.0 nM. The hydrophilicity and large polar surface area of the potent S1-S1'-S2' binding FXIa inhibitors compromised permeability. Initial work to expand the 6-chloro-3,4-dihydro-1H-quinolin-2-one fragment towards the prime side to yield molecules with less hydrophilicity shows promise to afford potent, selective and orally bioavailable compounds.