16063-16-4

Usage

Classification

Quinoline derivative and sulfone

Contains

Methylsulfinyl group

Potential properties

Medicinal, anti-inflammatory, and anti-tumor

Possible applications

Drug development, organic synthesis, and as a building block for new compounds with pharmaceutical potential

Importance

Of interest for its potential pharmacological and synthetic applications

Upstream product

• 83936-11-2 4-methoxy-3-methylsulfanylquinoline 
• 802913-36-6 1-methyl-3-methylsulfinyl-1,4-dihydro-4-thiooxoquinoline 
• 142349-10-8 1-methyl-3-methylthio-4-thioxo-1,4-dihydroquinoline 
• 66424-83-7 1-methyl-3-methylthio-4-oxo-1,4-dihydroquinoline 

Relevant academic research and scientific papers

Synthesis of 1-methyl-3-methylthio- and 1-methyl-3-methylsulfinyl-4- substituted 2(1H)-quinolinones

Treatment of 4-substituted (X=Cl, OCH3, SCH3) quinolinium salts (2) in aqueous-DMSO solution with K3[Fe(CN) 6]/NaOH system led to the respective 2-quinolinones (3) (60-69%) which were accompanied by 1-methyl-3-methylthio-4-quinolinone (8) (ca. 20%). 3-Methylthio substituent in quinolines (1), 4-quinolinethione (5) and 2-quinolinones (3) underwent S-oxidation to a sulfinyl group when the compounds (1), (3) and (5) were treated with nitrating mixture (-5 °C, 1 mol. eqv. of HNO3), but with an excess of nitric acid 2-quinolinones (3) were transformed to the respective 3-methylsulfinyl-6-nitro derivatives (7). The reaction of 4-chloroquinolines (1a), (3a) (at 140-160 °C) and (4a) (at 0 °C) with dimethylamine gave high yield of the 4-dimethylamino derivatives (1d), (3d) and (4d), respectively.

Synthesis of 3-alkylsulfinyl-4(1H)-quinolinones from 4-methoxy-3- alkylthioquinolines

Reactions of 4-methoxy- or 1,4-dihydro-4-oxo-3-alkylthioquinolines (1) and (4, 5) with a nitrating mixture ran as the 3-alkylthio group S- monooxidation and led to the respective alkylsulfinyl derivatives (2, 3 or 6). Hydrolysis of 4-methoxy-3-alkylsulfinylquinolines (2) with hydrochloric acid (1:1) at 65-68 °C gave 3-alkylsulfinyl-4(1H)-quinolinones (3).

Method of treating heart disease

A method for the treatment of heart failure in a mammal comprises the administration to the mammal of a quinolone of the general formula I, STR1 wherein m is 0 or 1; n is 0, 1 or 2; and R is hydrogen, halo, methyl or trifluoromethyl. A preferred method of the invention comprises the treatment of chronic heart failure in a mammal by the oral administration of a quinolone of formula I. Preferred compounds of formula I are 7-fluoro-1-methyl-3-methylsulphinyl-4-quinolone and 1-methyl-3-methylsulphonylmethyl-4-quinolone.