15446-25-0

Basic information

• Product Name: Acetic acid, [(4-chlorophenyl)sulfonyl]-, methyl ester
• CAS NO: 15446-25-0
• Molecular Formula: C9H9ClO4S
• Molecular Weight: 248.687
• Mol File: 15446-25-0.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Acetic acid, [(4-chlorophenyl)sulfonyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid, [(4-chlorophenyl)sulfonyl]-, methyl ester(15446-25-0)
• EPA Substance Registry System: Acetic acid, [(4-chlorophenyl)sulfonyl]-, methyl ester(15446-25-0)

Safety Data

• Hazardous Substances Data: 15446-25-0(Hazardous Substances Data)

Upstream product

• 14752-66-0 sodium p-chlorobenzenesulphinate 
• 96-34-4 methyl chloroacetate 
• 1679-18-1 4-Chlorophenylboronic acid 
• 96-32-2 bromoacetic acid methyl ester 
• 105-39-5 chloroacetic acid ethyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 3405-89-8 2-(4-chloro-phenylsulfonyl)acetic acid 
• 74-88-4 methyl iodide 
• 3405-88-7 (4-chlorophenylthio)acetic acid 
• 67-56-1 methanol 

Downstream Products

• 94143-10-9 methyl 2-(4-chlorophenylsulfonyl)-3-phenylpropionate 
• 94143-12-1 methyl 2-(4-chlorophenylsulfonyl)-2-benzyl-3-phenylpropionate 
• 94143-07-4 methyl 2-(4-chlorophenylsulfonyl)propionate 
• 36107-11-6 ((4-chlorophenyl)sulfonyl)acetohydrazide 
• 836610-59-4 2-(4-chloro-benzenesulfonyl)-N-(2-hydroxy-ethyl)-acetamide 
• 1093733-93-7 7-chloro-3-(4-chloro-benzenesulfonyl)-4-(4-fluoro-phenyl)-quinoline 
• 836610-65-2 2-(4-chloro-benzenesulfonyl)-N-(2-chloro-ethyl)-acetamide 
• 3937-96-0 tosylacetic acid 
• 7164-71-8 2-(4-chloro-benzenesulfonyl)-N-hydroxy-acetamide 
• 106307-48-6 3-(4-Chlorophenylsulfonylmethyl)-5-hydroxy-1,2,4-triazole 
• 3405-89-8 2-(4-chloro-phenylsulfonyl)acetic acid 
• 94143-08-5 methyl 2-(4-chlorophenylsulfonyl)butyrate 
• 94143-13-2 methyl 2-(4-chlorophenylsulfonyl)2-ethylbutyrate 

Relevant articles and documents

Synthesis and Pharmacological Activity of Tris(2-hydroxyethyl)ammonium 4-Chlorophenylsulfonylacetate

Methods for the synthesis of 4-chlorophenylsulfonylacetic acid and its tris(2-hydroxyethyl)ammonium salt (“sulfacetamine”) were studied. The results of in vitro and in vivo experiments showed that sulfacetamine possesses high antithrombotic, antioxidant, hypocholesterolemic, immunostimulating, and protective-adaptive activities.

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.

SULFONYL-QUINOLINE DERIVATIVES

New mGluRl and mGluR5 receptor subtype preferring ligands of formula: (I) and/or salts and/or hydrates and/or solvates thereof, to the processes and intermediates for their preparation, to pharmaceutical compositions containing these compounds and to thei