121-58-4

Usage

Uses

Used in Pharmaceutical Industry:
4-(Dimethylamino)benzenesulphonic acid is used as a weak yeast sirtuin inhibitor for its potential role in the development of therapeutic agents targeting sirtuin enzymes. Sirtuins are known to play a role in various cellular processes, including aging, metabolism, and stress response, and their inhibition can have therapeutic benefits in treating certain diseases.
Used in Chemical Synthesis:
4-(Dimethylamino)benzenesulphonic acid can be used as a starting material or intermediate in the synthesis of various organic compounds, including pharmaceuticals, dyes, and other specialty chemicals. Its unique functional groups allow for versatile chemical reactions and modifications, expanding its potential applications in the chemical industry.
Used in Analytical Chemistry:
Due to its acidic and sulfonic acid properties, 4-(Dimethylamino)benzenesulphonic acid can be employed as a reagent or buffer component in various analytical techniques, such as chromatography, electrophoresis, and titration. Its ability to interact with other molecules and ions makes it a valuable tool for separation and detection processes in analytical chemistry.
Used in Material Science:
The unique combination of a dimethylamino group and a sulfonic acid group in 4-(Dimethylamino)benzenesulphonic acid can be utilized in the development of new materials with specific properties, such as conductivity, solubility, or stability. It can be incorporated into polymers, coatings, or other materials to enhance their performance or introduce new functionalities.

InChI:InChI=1/C8H11NO3S/c1-9(2)7-3-5-8(6-4-7)13(10,11)12/h3-6H,1-2H3,(H,10,11,12)

Upstream product

• 121-69-7 N,N-dimethyl-aniline 
• 77-78-1 dimethyl sulfate 
• 121-57-3 4-aminobenzene sulfonic acid 
• 50-00-0 formaldehyd 
• 14503-46-9 2-dimethylamino-benzenesulfonic acid 
• 19715-49-2 4-(dimethylamino)benzenesulfonyl chloride 
• 35478-69-4 dimethylphenylamidosulfonic acid 
• 58888-49-6 N,N-dimethyl-N-phenylammonium hydrogen sulfate 
• 874-52-2 N,N-dimethylaniline N-oxide 

Downstream Products

• 19715-49-2 4-(dimethylamino)benzenesulfonyl chloride 
• 89977-93-5 N,N-dimethyl-2,3,4-trinitro-aniline 
• 14503-46-9 2-dimethylamino-benzenesulfonic acid 
• 618-09-7 N,N-dimethyl-m-aminobenzenesulfonic acid 
• 121-69-7 N,N-dimethyl-aniline 
• 100-23-2 N,N-Dimethyl-4-nitroaniline 
• 943-41-9 N-methyl-N-nitroso-4-nitroaniline 
• 426820-04-4 dimethyl-[4-(2-tridecyl-4-trityl-piperazine-1-sulfonyl)-phenyl]-amine 

Relevant academic research and scientific papers

Evaluation of benzoic acid derivatives as sirtuin inhibitors

Employing a genetically modified yeast strain as a screening tool, 4-dimethylaminobenzoic acid (5) was isolated from the marine sediment-derived Streptomyces sp. CP27-53 as a weak yeast sirtuin (Sir2p) inhibitor. Using this compound as a scaffold, a series of disubstituted benzene derivatives were evaluated to elucidate the structure activity relationships for Sir2p inhibition. The results suggested that 4-alkyl or 4-alkylaminobenzoic acid is the key structure motif for Sir2p inhibitory activity. The most potent Sir2p inhibitor, 4-tert-butylbenzoic acid (20), among the tested compounds in this study turned out to be a weak but selective SIRT1 inhibitor. The calculated binding free energies between the selected compounds and the catalytic domain of SIRT1 were well correlated to their measured SIRT1 inhibitory activities.

Evaluation of benzoic acid derivatives as sirtuin inhibitors

Employing a genetically modified yeast strain as a screening tool, 4-dimethylaminobenzoic acid (5) was isolated from the marine sediment-derived Streptomyces sp. CP27-53 as a weak yeast sirtuin (Sir2p) inhibitor. Using this compound as a scaffold, a series of disubstituted benzene derivatives were evaluated to elucidate the structure activity relationships for Sir2p inhibition. The results suggested that 4-alkyl or 4-alkylaminobenzoic acid is the key structure motif for Sir2p inhibitory activity. The most potent Sir2p inhibitor, 4-tert-butylbenzoic acid (20), among the tested compounds in this study turned out to be a weak but selective SIRT1 inhibitor. The calculated binding free energies between the selected compounds and the catalytic domain of SIRT1 were well correlated to their measured SIRT1 inhibitory activities.

BORON-CONTAINING SMALL MOLECULES

This invention relates to, among other items, 6-substituted benzoxaborole compounds and their use for treating bacterial infections.

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.

Structure-activity relationships in platelet-activating factor (PAF). 11-From PAF-antagonism to phospholipase A2 inhibition: Syntheses and structure-activity relationships in 1-arylsulfamido-2-alkylpiperazines

1-Benzoyl-2-alkyl piperazines are strong inhibitors of Group I and II secreted PLA2s. An improvement of their activity was obtained by replacing the amide function by a sulfamide and by introduction of electrodonor substituents on the para position of the benzenesulfonyl moiety. Neither the position on one of the carbon of the piperazine ring nor the absolute configuration of this carbon have an effect on the affinity for one or the other group of PLA2, but the lipophilicity remains for these series an essential parameter. In addition structure-activity relationships allow new hypothesis on interaction of these piperazine derivatives with the catalytic site of PLA2s.

Effect of Microwave Heating on Organic Reactions of Different Types

Sulfonation of N,N-dimethylaniline, dehydration of succinic acid, and synthesis of 3′,6′-dihydroxyspiro(isobenzofuran-1,9′-xanthen)-3-one occur in the same or similar way under both microwave and convection heating.

New classes of antimuscarinic agents endowed with selective antispasmodic properties. 1-Arylsulfonyl pyrrolidin-2-ones and 2-thiones, 1-arylsulfonyl piperidin-2-ones and 2-thiones and 1-arylsulfonyl hexahydro-2H-azepin-2-one

A series of 1-arylsulfonylpyrrolidin-2-ones (and 2-thiones), 1-aryl sulfonylpiperidin-2-ones (and 2-thiones) and 1-arylsulfonyl hexahydro-2H-azepin-2-one were synthesized and submitted to a battery of binding assays. The compounds showed little or no affinity for the receptors tested other than muscarinic receptors labelled either with [3H]pirenzepine or with [3H]quinuclidinyl benzilate. When tested in the isolated guinea pig ileum, they antagonized the contractions induced by acetylcholine and behaved as competitive muscarinic antagonists. After parenteral administration in mice, most compounds inhibited carbachol-induced diarrhoea but were less effective in counteracting salivation and lacrimation and showed little or no mydriatic action, thus displaying selectivity at the intestinal level. The reference drugs tested, atropine, butyl scopolamine and cimetropium bromide were far less selective. Maximal in vivo activity was obtained by introducing diethylamino or 1-piperidino or 1-hexahydroazepinyl groups in the 4-position of the phenyl ring while the enlargement of a 5- to a 6-membered lactam ring or its conversion into a thiolactam had a less marked effect. The most interesting compounds were further evaluated for their ability to antagonize carbachol-induced colonic hypermotility in the rat and arecoline-induced analgesia in mice. The effect on gastric acid secretion in the rat was also investigated. The overall in vivo data showed that compounds 14, 15, 26 and 27, i.e. those bearing a 1-hexahydroazepinyl group in the 4-position of the phenyl ring, were the most potent and selective compounds. Unlike the reference drugs, they antagonized carbachol-induced diarrhoea and colonic hypermotility at doses (0.6-4 mg/kg i.p.) 1-2 orders of magnitude lower than those needed to counteract carbachol-induced salivation and lacrimation or to induce mydriatic and antisecretory effects. The novelty of these structures and their selectivity of action on smooth muscle are the two key features of this class of antimuscarinics.

ISOMERIC TRANSFORMATIONS OF AMINOSULFONIC ACIDS OF THE BENZENE SERIES IN MIXTURES OF SULFURIC AND ACETIC ACIDS

The isomerization rate of aminosulfonic acids in anhydrous binary mixtures of sulfuric and acetic acids is lower than in aqueous sulfuric acid solutions but higher than in 100percent sulfuric acid.This is explained by the differences in the structure and activity of the proton carriers during desulfonation.The rate of transformation of the labile isomers into the meta isomers increases with increase in the acidity of the medium, and this is due to the increase in the resulfonation rate of the protonating molecules of the amines formed during the desulfonation of the aminosulfonic acids.The effect of mercuric sulfate on the isomeric transformations of aminosulfonic acids is explained by the mercuration of the protonated molecules of the amines, which takes place at higher rates than their sulfonation and leads to the formation of the meta-mercury derivatives of the amines.The latter are than converted into the m-aminosulfonic acids by the action of concentrated sulfuric acid.