90548-91-7

Basic information

• Product Name: 1-Propanone, 3-(dimethylamino)-1-(3-methylphenyl)-
• CAS NO: 90548-91-7
• Molecular Formula: C12H17NO
• Molecular Weight: 191.273
• Mol File: 90548-91-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-Propanone, 3-(dimethylamino)-1-(3-methylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Propanone, 3-(dimethylamino)-1-(3-methylphenyl)-(90548-91-7)
• EPA Substance Registry System: 1-Propanone, 3-(dimethylamino)-1-(3-methylphenyl)-(90548-91-7)

Safety Data

• Hazardous Substances Data: 90548-91-7(Hazardous Substances Data)

Upstream product

• 50-00-0 formaldehyd 
• 506-59-2 N,N-dimethylammonium chloride 
• 585-74-0 3-Methylacetophenone 

Downstream Products

• 1440663-13-7 (E)-3-(5-methylthiophen-2-yl)-1-m-tolylprop-2-en-1-one 
• 1029135-04-3 C₁₄H₁₅N₅ 

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.

Synthesis and evaluation of analogues of the tuberculosis drug bedaquiline containing heterocyclic B-ring units

Analogues of bedaquiline where the phenyl B-unit was replaced with monocyclic heterocycles of widely differing lipophilicity (thiophenes, furans, pyridines) were synthesised and evaluated. While there was an expected broad positive correlation between lipophilicity and anti-TB activity, the 4-pyridyl derivatives appeared to have an additional contribution to antibacterial potency. The majority of the compounds were (desirably) more polar and had higher rates of clearance than bedaquiline, and showed acceptable oral bioavailability, but there was only limited (and unpredictable) improvement in their hERG liability.

PYRAZOLE CARBOXAMIDE COMPOUNDS, COMPOSITIONS AND METHODS OF USE

Provided herein are compounds of formula (AA): N N H HN O N N R R 6 A (R a ) p, (AA) stereoisomers or a pharmaceutically acceptable salt thereof, wherein A, R a, p, R and R 6 are defined herein, compositions including the compounds and methods of manufacturing and using the compounds for the treatment of diseases.