4543-58-2

Usage

Uses

Used in Pharmaceutical Industry:
Benzenesulfonamide, 2,4,6-trimethyl(9CI) is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic benefits.
Used in Dye Industry:
In the dye industry, Benzenesulfonamide, 2,4,6-trimethyl(9CI) is utilized as an intermediate in the production of dyes, leveraging its chemical properties to create a range of colorants for different applications.
Used in Agricultural Applications:
Benzenesulfonamide, 2,4,6-trimethyl(9CI) is employed as a biocide in agriculture to control microbial growth that can harm crops, thereby contributing to crop protection and yield enhancement.
Used in Industrial Applications:
In industrial settings, Benzenesulfonamide, 2,4,6-trimethyl- (9CI) is used as a biocide to prevent the growth of microorganisms in various processes and systems, helping to maintain the efficiency and longevity of industrial equipment and products.
Used in Medical Treatments:
Benzenesulfonamide, 2,4,6-trimethyl(9CI) has potential applications in the medical field, particularly when used in combination with other drugs, to treat certain conditions, capitalizing on its antimicrobial properties to enhance therapeutic outcomes.

InChI:InChI=1/C9H13NO2S/c1-6-4-7(2)9(8(3)5-6)13(10,11)12/h4-5H,1-3H3,(H2,10,11,12)

Upstream product

• 773-64-8 2-mesitylenesulphonyl chloride 
• 161452-12-6 N-(tert-butyl)-2,4,6-trimethylbenzenesulfonamide 
• 1336-21-6 ammonium hydroxide 
• 863033-36-7 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[6-oxo-1-(2,4,6-trimethyl-benzenesulfonyl)-1,6-dihydro-purin-9-yl]-tetrahydro-furan-3-yl ester 
• 62-53-3 aniline 
• 71100-55-5 1-mesitylenesulfonyl-4-nitroimidazole 

Downstream Products

• 93808-40-3 N-butyl-N'-(2,4,6-trimethyl-benzenesulfonyl)-urea 
• 121446-35-3 9,10-Bis- 
• 148838-27-1 N-2,4,6-trimethylphenylsulfonylbenzaldimine 
• 186800-71-5 2,4,6-Me₃C₆H₂-SO₂NSO 
• 189340-71-4 N,N-Bis-[4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-2,4,6-trimethyl-benzenesulfonamide 
• 205517-03-9 3-sulfamoyl-2,4,6-trimethylaniline 
• 304862-71-3 1,6,11-tris(mesitylenesulfonyl)-1,6,11-triaza-(3Z,8Z)-tridecatriene 
• 304862-63-3 N³,N⁸,N¹³,N¹⁸,N²³-pentakis(mesityelenesulfonyl)-3,8,13,18,23-pentaaza-(5Z,10Z,15Z,20Z)-pentacosatetraene 
• 304862-67-7 1,6,11-tris(mesitylenesulfonyl)-1,6,11-triaza-(3Z)-tridecene 
• 304862-65-5 N³,N⁸,N¹³,N¹⁸,N²³-pentakis(mesitylenesulfonyl)-3,8,13,18,23-pentaaza-(10Z,15Z)-pentacosadiene 
• 304862-61-1 N³,N⁸,N¹³,N¹⁸,N²³-pentakis(mesitylenesulfonyl)-3,8,13,18,23-pentaaza-(5Z,20Z)-pentacosadiene 
• 656827-55-3 N-[(2,4,6-trimethylphenyl)sulfonyl]carbamic acid methyl ester 
• 943249-73-8 pivaraldehyde N-(mesitylenesulfonyl)imine 
• 881813-31-6 (S)-N-(mesitylenesulfonyl)-α-(cyano)cyclohexylmethylamine 

Relevant academic research and scientific papers

Deconstructing Noncovalent Kelch-like ECH-Associated Protein 1 (Keap1) Inhibitors into Fragments to Reconstruct New Potent Compounds

Targeting the protein-protein interaction (PPI) between nuclear factor erythroid 2-related factor 2 (Nrf2) and Kelch-like ECH-associated protein 1 (Keap1) is a potential therapeutic strategy to control diseases involving oxidative stress. Here, six classes of known small-molecule Keap1-Nrf2 PPI inhibitors were dissected into 77 fragments in a fragment-based deconstruction reconstruction (FBDR) study and tested in four orthogonal assays. This gave 17 fragment hits of which six were shown by X-ray crystallography to bind in the Keap1 Kelch binding pocket. Two hits were merged into compound 8 with a 220-380-fold stronger affinity (Ki = 16 μM) relative to the parent fragments. Systematic optimization resulted in several novel analogues with Ki values of 0.04-0.5 μM, binding modes determined by X-ray crystallography, and enhanced microsomal stability. This demonstrates how FBDR can be used to find new fragment hits, elucidate important ligand-protein interactions, and identify new potent inhibitors of the Keap1-Nrf2 PPI.

SELECTIVE NON-CYCLIC NUCLEOTIDE ACTIVATORS FOR THE CAMP SENSOR EPAC1

The invention relates generally to novel EPAC1 activators, such as Formula (I) and (II) and the preparation thereof as well as the use of EPAC1 activators disclosed herein as to selectively activate EPAC1 in cells.

Unlocking Amides through Selective C–N Bond Cleavage: Allyl Bromide-Mediated Divergent Synthesis of Nitrogen-Containing Functional Groups

We report a new set of reactions based on the unlocking of amides through simple treatment with allyl bromide, creating a common platform for accessing a diverse range of nitrogen-containing functional groups such as primary amides, sulfonamides, primary amines, N-acyl compounds (esters, thioesters, amides), and N-sulfonyl esters. The method has potential industrial applicability, as demonstrated through gram-scale syntheses in batch and in a continuous flow system.

Synthesis and Biochemical Evaluation of Noncyclic Nucleotide Exchange Proteins Directly Activated by cAMP 1 (EPAC1) Regulators

Exchange proteins directly activated by cAMP (EPAC) play a central role in various biological functions, and activation of the EPAC1 protein has shown potential benefits for the treatment of various human diseases. Herein, we report the synthesis and biochemical evaluation of a series of noncyclic nucleotide EPAC1 activators. Several potent EPAC1 binders were identified including 25g, 25q, 25n, 25u, 25e, and 25f, which promote EPAC1 guanine nucleotide exchange factor activity in vitro. These agonists can also activate EPAC1 protein in cells, where they exhibit excellent selectivity toward EPAC over protein kinase A and G protein-coupled receptors. Moreover, 25e, 25f, 25n, and 25u exhibited improved selectivity toward activation of EPAC1 over EPAC2 in cells. Of these, 25u was found to robustly inhibit IL-6-activated signal transducer and activator of transcription 3 (STAT3) and subsequent induction of the pro-inflammatory vascular cell adhesion molecule 1 (VCAM1) cell-adhesion protein. These novel EPAC1 activators may therefore act as useful pharmacological tools for elucidation of EPAC function and promising drug leads for the treatment of relevant human diseases.

Electrochemically generatedN-iodoaminium species as key intermediates for selective methyl sulphonylimination of tertiary amines

Reported herein is a straightforward protocol for approachingN-sulphonylamidinesviaan electricity-driven, iodine-mediated cross dehydrogenative condensation (CDC) between sulphonamides and tertiary amines, which features exclusive N-CH3selectivity for the amine partners. Mechanistic studies indicate that anin situgeneratedN-iodoaminium species serves as the key intermediate.

Sulfonamide compound and synthesis method and application thereof

The invention discloses a synthesis method of a sulfonamide compound represented in a formula (2). According to the method, diazonium salt is used as a reaction raw material, and under the action of an inorganic nitrogen reagent, an inorganic sulfur dioxide reagent, an additive and a phosphine reagent, the diazonium salt is reacted in a solvent at 60-100 DEG C to obtain various sulfonamide compounds. According to the method inorganic salt is used as a nitrogen atom source and a sulfur dioxide source under a metal-free catalytic condition to construct the sulfonamide compound through one step,thereby avoiding the conventional multi-step synthesis of sulfonamide by condensing unstable acid chloride and amine; and the developed sulfonamide synthesis method can be further applied to the synthesis of the arthritis drug celecoxib and the psychotropic drug sulpiride.

Multiprotein Dynamic Combinatorial Chemistry: A Strategy for the Simultaneous Discovery of Subfamily-Selective Inhibitors for Nucleic Acid Demethylases FTO and ALKBH3

Dynamic combinatorial chemistry (DCC) is a powerful supramolecular approach for discovering ligands for biomolecules. To date, most, if not all, biologically templated DCC systems employ only a single biomolecule to direct the self-assembly process. To expand the scope of DCC, herein, a novel multiprotein DCC strategy has been developed that combines the discriminatory power of a zwitterionic “thermal tag” with the sensitivity of differential scanning fluorimetry. This strategy is highly sensitive and could differentiate the binding of ligands to structurally similar subfamily members. Through this strategy, it was possible to simultaneously identify subfamily-selective probes against two clinically important epigenetic enzymes: FTO (7; IC50=2.6 μm) and ALKBH3 (8; IC50=3.7 μm). To date, this is the first report of a subfamily-selective ALKBH3 inhibitor. The developed strategy could, in principle, be adapted to a broad range of proteins; thus it is of broad scientific interest.

Metal-free construction of primary sulfonamides through three diverse salts

In this report, the first metal-free construction of primary sulfonamides through a direct three-component reaction of sodium metabisulfite, sodium azide and aryldiazonium has been established. Readily available inorganic Na2S2O5 and NaN3 were applied as the sulfur dioxide surrogate and nitrogen source respectively. The widely used sulfonamide drugs Celecoxib and Sulpiride, which possess multiple heteroatoms and active hydrogen containing functional groups, are efficiently installed with -SO2NH2 groups at a late stage. Control experiments and kinetic studies demonstrated that aryl radicals, sulfonyl radicals and conjugated phosphine imine radicals are involved in this transformation.

THIAZOLIDINONE COMPOUNDS AND USE THEREOF

A pharmaceutical composition containing a compound of Formula (I) for treating an opioid receptor-associated condition. Also disclosed is a method for treating an opioid receptor-associated condition using such a compound. Further disclosed are two sets of thiazolidinone compounds of formula (I): (i) compounds each having an enantiomeric excess greater than 90% and (ii) compounds each being substituted with deuterium.

Discovery of novel DAPY-IAS hybrid derivatives as potential HIV-1 inhibitors using molecular hybridization based on crystallographic overlays

Crystallographic overlap studies and pharmacophoric analysis indicated that diarylpyrimidine (DAPY)-based HIV-1 NNRTIs showed a similar binding mode and pharmacophoric features as indolylarylsulfones (IASs), another class of potent NNRTIs. Thus, a novel series of DAPY-IAS hybrid derivatives were identified as newer NNRTIs using structure-based molecular hybridization. Some target compounds exhibited moderate activities against HIV-1 IIIB strain, among which the two most potent inhibitors possessed EC50 values of 1.48?μM and 1.61?μM, respectively. They were much potent than the reference drug ddI (EC50?=?76.0?μM) and comparable to 3TC (EC50?=?2.54?μM). Compound 7a also exhibited the favorable selectivity index (SI?=?80). Preliminary structure-activity relationships (SARs), structure-cytotoxicity relationships, molecular modeling studies, and in silico calculation of physicochemical properties of these new inhibitors were also discussed.