18704-37-5

Usage

Uses

Used in Pharmaceutical Industry:
8-Quinolinesulfonyl chloride is used as a coupling reagent in oligonucleotide synthesis for the development of pharmaceutical compounds. Its reactivity allows for the formation of stable linkages between nucleotide units, which is crucial for the synthesis of therapeutic oligonucleotides.
Used in Organic Chemistry:
8-Quinolinesulfonyl chloride is used as a reagent in the synthesis of olefins from secondary esters at moderate temperatures. This application is valuable in organic chemistry for the production of olefins, which are important building blocks for a wide range of chemical compounds and materials.
These uses highlight the versatility of 8-Quinolinesulfonyl chloride as a chemical intermediate in both pharmaceutical and organic chemistry applications. Its reactivity and ability to form water-soluble compounds make it a valuable tool in the synthesis of various compounds.

InChI:InChI=1/C7H11BrN2/c1-7(2,3)6-5(8)4-9-10-6/h4H,1-3H3,(H,9,10)

Upstream product

• 35203-91-9 8-quinolinesulfonamide 
• 491-33-8 8-mercaptoquinoline 
• 1160-28-7 bis(8-quinolinyl)disulfide 
• 16567-18-3 8-bromoquinoline 
• 91-22-5 quinoline 
• 142597-99-7 1-(quinoline-8-sulphonyl)-3-n-butylurea 
• 85-48-3 8-quinolinesulfonic acid 

Downstream Products

• 117800-91-6 trans-4-tert-butylcyclohexyl 8-quinolinesulfonate 
• 108293-28-3 (-)-<(-)-menthyl 8-quinolinesulfinate> 
• 117800-93-8 l-menthyl 8-quinolinesulfonate 
• 104502-94-5 N_α-(8-Chinolinsulfonyl)-4-cyanphenylalanin 
• 77244-88-3 8-quinolenesulfonyl-3-nitro-1,2,4-triazole 
• 83906-30-3 5'-O-quinolinesulfonyl-2',3'-O-dibenzoyluridine 
• 62862-08-2 cyclohexylmethyl 8-quinolinesulfonate 
• 117800-87-0 cyclohexyl 8-quinolinesulfonate 
• 215511-35-6 Quinoline-8-sulfonic acid (2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)-amide 
• 215511-68-5 Quinoline-8-sulfonic acid [5-(3-nitro-phenyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl]-amide 
• 197959-98-1 5-methyl-3-(quinolinyl-8-sulfonyloxy)phenol 

Relevant academic research and scientific papers

Copper-Catalyzed N-Directed Distal C(sp3)-H Sulfonylation and Thiolation with Sulfinate Salts

We herein report a selective and catalytic C(sp3)-H functionalization approach to access amines bearing organo-sulfonyl and organo-thiol groups. This reaction proceeds through a cascade process of N-radical formation, alkyl radical formation via 1,5-HAT, and C-S bond formation, thereby offering a series of functionalized amines. This method could enable primary, secondary, and tertiary C(sp3)-H sulfonylation and thiolation and also exhibits good functional group tolerance.

Synthesis, Characterization, and Theoretical Studies of cis -Dichloridobis(8-quinolinethiolato)tin(iv) and bis(8-Sulfanylquinolinium) Hexachloridostannate(iv) Derivatives

The structural characterisation of bis(8-sulfanylquinolinium) hexachloridostannate(iv) (2) is reported and the variable reaction behaviour of this compound in different solvents has been explored. In particular, attempted recrystallization of 2 from chloroform and dichloromethane affords two polymorphs of cis-dichloridobis(8-quinolinethiolato)tin(iv), 3m and 3t, respectively. Attempted recrystallization of 2 from methanol gives crystals of 8,8′-dithiodiquinolinium hexachloridostannate(iv) 4. When 2 is dissolved in dimethyl sulfoxide in the presence of air, it undergoes oxidation to afford diquinolinyl-8,8′-disulfide 5. The molecular structures of the isolated compounds 2-4 are unambiguously authenticated by single crystal X-ray diffraction studies. The electronic structure properties of all the isolated compounds 2-4 are thoroughly studied by DFT calculations.

Preparation method of genotoxic fasudil hydrochloride impurities

The invention relates to a preparation method of genotoxic fasudil hydrochloride impurities. The preparation method specifically comprises the following steps: preparing the fasudil hydrochloride impurities including methyl 5-isoquinolinesulfonate, ethyl 5-isoquinolinesulfonate, methyl 8-isoquinolinesulfonate, ethyl 8-isoquinolinesulfonate, methyl 5-quinolinesulfonate, ethyl 5-quinolinesulfonate,methyl 8-quinolinesulfonate and ethyl 8-quinolinesulfonate: firstly preparing isoquinolinesulfonyl chloride hydrochloride or quinolinesulfonyl chloride hydrochloride from isoquinoline sulfonic acid orquinoline sulfonic acid used as an initial raw material and thionyl chloride, and then reacting the isoquinolinesulfonyl chloride hydrochloride or quinolinesulfonyl chloride hydrochloride with methylalcohol and ethyl alcohol respectively to generate the corresponding fasudil hydrochloride methyl ester and ethyl ester impurities. The invention also provides a method for synthesizing the genotoxicfasudil hydrochloride impurityies with high purity to solve the problems of poor stability, easy rearrangement and easy decomposition of methyl quinolinesulfonate and ethyl ester.

SULFONAMIDE OR AMIDE COMPOUNDS, COMPOSITIONS AND METHODS FOR THE PROPHYLAXIS AND/OR TREATMENT OF AUTOIMMUNE, INFLAMMATION OR INFECTION RELATED DISORDERS

The present invention related to novel sulfonamides or amides as TLR-4 antagonists, and pharmaceutical formulations containing the same and the methods of use thereof. Uses of the present novel sulfonamides or amides include, but are not limited to, the prophylaxis and/or treatment of autoimmune, inflammation, or infection related disorders.

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.

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.

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).

Phenylenediamine urotensin-II receptor antagonists and CCR-9 antagonists

The present invention relates to urotensin II receptor antagonists, CCR-9 antagonists, pharmaceutical compositions containing them and their use.

A convenient synthesis of novel 3-(heterocyclylsulfonyl)propanoic acids and their amide derivatives

A large number of novel 3-(heterocyclylsulfonyl)propanoic acids and their amide derivatives were prepared in good yields and excellent purity starting from the corresponding heterocyclic compounds. At first, chlorosulfonates were generated by reaction of initial heterocycles with various sulfonating and chlorinating agents followed by their conversion into sodium sulfinates. Treatment of sulfinates with acrylic acid smoothly afforded a series of sulfonylpropionates, which were used as convenient reagents for the preparation of a large number of the corresponding carboxamide derivatives.