654653-81-3

Basic information

• Product Name: (1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(3-fluorophenyl)-1-phenylbutan-2-ol
• CAS NO: 654653-81-3
• Molecular Formula: C₂₈H₂₈BrFN₂O₂
• Molecular Weight: 523.4365
• Mol File: 654653-81-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 635.2°C at 760 mmHg
• Flash Point: 337.9°C
• Density: 1.341g/cm³
• Vapor Pressure: 5.27E-17mmHg at 25°C
• Refractive Index: 1.627
• CAS DataBase Reference: (1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(3-fluorophenyl)-1-phenylbutan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(3-fluorophenyl)-1-phenylbutan-2-ol(654653-81-3)
• EPA Substance Registry System: (1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(3-fluorophenyl)-1-phenylbutan-2-ol(654653-81-3)

Safety Data

• Hazardous Substances Data: 654653-81-3(Hazardous Substances Data)

Upstream product

• 455-36-7 1-(3-fluorophenyl)ethanone 
• 654655-69-3 3-benzyl-6-bromo-2-methoxyquinoline 
• 582325-02-8 3-(dimethylamino)-1-(3-fluorophenyl)propan-1-one 
• 100-39-0 benzyl bromide 
• 99455-05-7 2-methoxy-6-bromoquinoline 

Relevant articles and documents

6-Cyano Analogues of Bedaquiline as Less Lipophilic and Potentially Safer Diarylquinolines for Tuberculosis

Bedaquiline (1) is a new drug for tuberculosis and the first of the diarylquinoline class. It demonstrates excellent efficacy against TB but induces phospholipidosis at high doses, has a long terminal elimination half-life (due to its high lipophilicity), and exhibits potent hERG channel inhibition, resulting in clinical QTc interval prolongation. A number of structural ring A analogues of bedaquiline have been prepared and evaluated for their anti-M.tb activity (MIC90), with a view to their possible application as less lipophilic second generation compounds. It was previously observed that a range of 6-substituted analogues of 1 demonstrated a positive correlation between potency (MIC90) toward M.tb and drug lipophilicity. Contrary to this trend, we discovered, by virtue of a clogP/M.tb score, that a 6-cyano (CN) substituent provides a substantial reduction in lipophilicity with only modest effects on MIC values, suggesting this substituent as a useful tool in the search for effective and safer analogues of 1.

USE OF SUBSTITUTED QUINOLINE DERIVATIVES FOR THE TREATMENT OF DRUG RESISTANT MYCOBACTERIAL DISEASES

The present invention relates to the use of a substituted quinoline derivative for the preparation of a medicament for the treatment of an infection with a drug resistant Mycobacterium strain wherein the substituted quinoline derivative is a compound according to Formula (Ia) or Formula (Ib) the pharmaceutically acceptable acid or base addition salts thereof, the stereochemically isomeric forms thereof, the tautomeric forms thereof and the N-oxide forms thereof. Also claimed is a composition comprising a pharmaceutically acceptable carrier and, as active ingredient, a therapeutically effective amount of the above compounds and one or more other antimycobacterial agents.