1360598-51-1

Basic information

• Product Name: 4-chloro-3-(phenylsulfonyl)quinoline
• Synonyms: 4-chloro-3-(phenylsulfonyl)quinoline
• CAS NO: 1360598-51-1
• Molecular Weight: 303.769
• Mol File: 1360598-51-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-chloro-3-(phenylsulfonyl)quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-3-(phenylsulfonyl)quinoline(1360598-51-1)
• EPA Substance Registry System: 4-chloro-3-(phenylsulfonyl)quinoline(1360598-51-1)

Safety Data

• Hazardous Substances Data: 1360598-51-1(Hazardous Substances Data)

Upstream product

• 1360598-44-2 methyl 2-phenylsulfonyl-3-ethoxyacrylate 
• 34097-60-4 methyl benzenesulfonylacetate 
• 5535-48-8 PVS 
• 134-20-3 2-carbomethoxyaniline 
• 64965-47-5 3-bromo-4-hydroxyquinoline 
• 1360598-50-0 3-(phenylsulfonyl)quinoline-4-ol 
• 1360598-49-7 3-phenylthioquinolin-4-ol 
• 3111-52-2 potassium thiophenolate 

Downstream Products

• 1360597-99-4 methyl-(3-phenylsulfonylquinolin-4-yl)amine 

Relevant articles and documents

Discovery of 4-amino-3-arylsulfoquinolines, a novel non-acetylenic chemotype of metabotropic glutamate 5 (mGlu5) receptor negative allosteric modulators

Negative allosteric modulators of metabotropic glutamate receptor 5 (mGlu5) showed efficacy in a number of animal models of different CNS diseases including anxiety and depression. Virtually all of the compounds which reached the clinic belong to the same chemotype having an acetylenic linker that connects (hetero)cyclic moieties. Searching for new chemotypes we identified a morpholino-sulfoquinoline derivative (1) by screening our corporate compound deck. The HTS hit showed reasonable affinity and selectivity towards mGlu5 receptors, however, its inferior metabolic stability prevented its testing in?vivo. In a chemical program we aimed to improve the affinity, physicochemical properties and metabolic stability exploring three regions of the hit. Systematic variation of different amines at position 4 (region I) led to the identification of 4-methyl-piperidinyl analogues. Substituents of the quinoline core (region II) and the phenylsulfonyl moiety (region III) were mapped by parallel synthesis. Evaluation of both morpholino- and 4-methyl-piperidinyl-sulfoquinoline libraries of about 270 derivatives revealed beneficial substituent combinations in regions II and III. Blood levels of optimized 4-methyl-piperidinyl-sulfoquinolines, however, were still insufficient for robust in?vivo efficacy. Finally, introducing 4-hydoxymethyl-piperidinyl substituent to region I resulted in new sulfoquinolines with greatly improved solubility and reasonable affinity coupled with affordable metabolic stability. The most promising analogues (24 and 25) showed high blood levels and demonstrated significant efficacy in the experimental model of anxiety.

SUBSTITUTED METHYL AMINES, SEROTONIN 5-HT6 RECEPTOR ANTAGONISTS, METHODS FOR PRODUCTION AND USE THEREOF

The present invention relates to novel substituted methyl-amines, serotonin 5-HT6 receptor antagonists, to active components, pharmaceutical compositions, method for prophylaxis and treatment of CNS diseases and “molecular tools”, in which novel substituted methyl-amines represent compounds of the general formula 1 and their crystalline forms and pharmaceutically acceptable salts, wherein: W represents benzene, naphthalene, indolizine, quinoline or oxazole cycle; R1=H, F, Cl; R2 represents hydrogen, fluoro, methyl, phenyl, thienyl, furan-2-yl, pyridyl, piperazin-1-yl or 4-methylpiperazin-1-yl; R3 represents cyclopropyl or optionally substituted methyl; with the exception of the compounds in which W simultaneously represents oxazole cycle and R2=phenyl or pyridyl.