159182-40-8

Usage

Chemical Properties

Yellow Solid

InChI:InChI=1/C9H6ClNO2S/c10-14(12,13)8-5-7-3-1-2-4-9(7)11-6-8/h1-6H

Upstream product

• 5332-24-1 3-bromoquinoline 
• 76076-35-2 3-mercaptoquinoline 
• 2769-32-6 3,3'-bisquinolinyl disulfide 
• 1207164-22-4 3-(benzylthio)quinoline 

Downstream Products

• 477739-42-7 C₂₇H₂₄FN₃O₅S₂ 
• 1135130-62-9 N-(2,5-dimethoxyphenyl)quinoline-3-sulfonamide 
• 1349893-83-9 N-(4-methyl-3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)quinoline-3-sulfonamide 
• 1360684-74-7 3-{4-[4-(4-chlorophenyl)piperazin-1-ylmethyl]piperidine-1-sulfonyl}quinoline 
• 1360625-61-1 3-{4-[4-(4-chlorophenyl)piperazin-1-ylmethyl]piperidine-1-sulfonyl}quinoline hydrochloride 
• 1360684-76-9 3-(4-{2-[4-(4-chlorophenyl)piperazin-1-yl]ethyl}piperidine-1-sulfonyl)quinoline 
• 1360625-63-3 3-(4-{2-[4-(4-chlorophenyl)piperazin-1-yl]ethyl}piperidine-1-sulfonyl)quinoline hydrochloride 
• 1360684-65-6 N-{3-[4-(4-chlorophenyl)piperazin-1-yl]propyl}-3-quinolinesulfonamide 
• 1360625-45-1 N-{3-[4-(4-chlorophenyl)piperazin-1-yl]propyl}-3-quinolinesulfonamide hydrochloride 
• 1360684-71-4 N-{4-[4-(3-chlorophenyl)piperazin-1-yl]butyl}-4-quinolinesulfonamide 
• 1360625-51-9 N-{4-[4-(3-chlorophenyl)piperazin-1-yl]butyl}-4-quinolinesulfonamide hydrochloride 
• 1360684-67-8 N-{4-[4-(3-chlorophenyl)piperazin-1-yl]butyl}-3-quinolinesulfonamide 
• 1360625-47-3 N-{4-[4-(3-chlorophenyl)piperazin-1-yl]butyl}-3-quinolinesulfonamide hydrochloride 
• 1364122-06-4 N-{3-[4-(4-chlorophenyl)piperazin-1-yl]pentyl}-3-quinolinesulfonamide 

Relevant academic research and scientific papers

Antidepressant and antipsychotic activity of new quinoline- and isoquinoline-sulfonamide analogs of aripiprazole targeting serotonin 5-HT 1A/5-HT2A/5-HT7 and dopamine D 2/D3 receptors

A series of new quinoline- and isoquinoline-sulfonamide analogs of aripiprazole was synthesized to explore the influence of two structural features-replacement of ether/amide moiety with sulfonamide one, and localization of a sulfonamide group in the azine moiety. In contrast to aripiprazole, compound 33 (N-(3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propyl) quinoline-7-sulfonamide) and 39 (N-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl) butyl)isoquinoline-3-sulfonamide) displaying multireceptor 5-HT 1A/5-HT2A/5-HT7/D2/D3 profile, and behaving as 5-HT1A agonists, D2 partial agonists, and 5-HT2A/5-HT7 antagonists, produced significant antidepressant activity in FST in mice. On the other hand, their 4-isoquinolinyl analog 40 (N-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butyl) isoquinoline-4-sulfonamide), with similar receptor binding and functional profile, additionally displayed remarkable antipsychotic properties in the MK-801-induced hyperlocomotor activity in mice.

Synthesis, 15N NMR spectra and GIAO calculated data of the seven positional isomers of 15N-labeled N,N-dimethylsulfamoylquinoline

The one-step synthesis of positional isomers of N,N- dimethylsulfamoylquinoline are presented. Seven newly synthesized compounds have been characterized by elemental analyses, MS, 1H and 15N NMR spectral data. The long-range correlations between the ring protons and the endocyclic nitrogen atoms were observed in the gHMBC experiments. The spectral positions of the nitrogen atoms from the sulfonamide groups were drawn from the 1D spectra of the 15N-labeled sulfonamide isotopomers. Correlations between the experimentally determined chemical shifts and GIAO calculated isotropic shielding constants were found. The GIAO calculations were based on HF-, MP2-, and B3LYP-optimized geometries and were performed at the HF, BLYP, and B3LYP levels of theory.

Efficient and scalable synthesis of pyridine sulfonamides

Short-step and scalable transformations from 2,6-dibromopyridine to 6-bromopyridine-2-sulfonamide by means of halogen-metal exchange and subsequent reaction with sulfuryl chloride followed by amidation are established. Application of the method for the synthesis of various pyridine sulfonamides is also described. Georg Thieme Verlag Stuttgart - New York.

A simple and highly effective oxidative chlorination protocol for the preparation of arenesulfonyl chlorides

2,4-Dichloro-5,5-dimethylhydantoin (DCDMH) was found to be a mild and efficient reagent for the direct oxidative conversion of sulfur compounds to the corresponding arenesulfonyl chlorides in good to excellent yields through oxidative chlorination. The method is suitable for many types of sulfur substrates (thiols, disulfides, and benzylic sulfides). The overall process is simple, practical, and it provides convenient access to a variety of aryl or heteroarylsulfonyl chlorides. The mild reaction conditions and the broad substrate scope render this method attractive and complementary to existing syntheses of aryl or heteroarylsulfonyl chlorides.

4' SUBSTITUTED COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY

The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein R1, R2, R5, R6, B, D, E, G, Q, x and n are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.

6' SUBSTITUTED COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY

The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein R1—R4 A, B, D, E, and G are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.

From haloquinolines and halopyridines to quinoline- and pyridinesulfonyl chlorides and sulfonamides

The action of sodium methanethiolate (in boiling DMF) towards haloazines (i.e. chloro- or bromo-pyridines and quinolines) (1) (with halogen substituent in non-aza-activated position) causes sequentially halogen ipso-substitution to methylthioazines (2) and then S-demethylation to azinethiolates (3A), which were: i) subjected to S-methylation, ii) oxidized to diazinyl disulfides (4) and iii) oxidatively chlorinated to azinesulfonyl chlorides (5). α- and γ-pyridine- and quinolinesulfonyl chlorides (5a, 5c, 5d and 5f) were prepared by oxidative chlorination of respective disulfides (4) performed in conc. hydrochloric acid and characterized by 1H and 13C NMR spectra. All azinesulfonyl chlorides (5) were effectively converted to corresponding azinesulfonamides (6).

Substituted phenyl sulfonamides as selective β 3 agonists for the treatment of diabetes and obesity

Substituted phenylsulfonamides are selective β 3 adrenergic receptor agonists with very little β 1 and β 2 adrenergic receptor activity and as such the compounds are capable of increasing lipolysis and energy expenditure in cells. The compounds thus have potent activity in the treatment of Type II diabetes and obesity. The compounds can also be used to lower triglyceride levels and cholesterol levels or raise high density lipoprotein levels or to decrease gut motility. In addition, the compounds can be used to reduced neurogenic inflammation or as antidepressant agents. The compounds are prepared by coupling an aminoalkylphenyl-sulfonamide with an appropriately substituted alkyl epoxide. Compositions and methods for the use of the compounds in the treatment of diabetes and obesity and for lowering triglyceride levels and cholesterol levels or raising high density lipoprotein levels or for increasing gut motility are also disclosed.