4543-58-2

Basic information

• Product Name: Benzenesulfonamide, 2,4,6-trimethyl- (9CI)
• Synonyms: Benzenesulfonamide, 2,4,6-trimethyl- (9CI);Mesitylene-2-sulphonamide, 2-Sulphamoylmesitylene;2,4,6-trimethylbenzene-1-sulfonamide
• CAS NO: 4543-58-2
• Molecular Formula: C₉H₁₃NO₂S
• Molecular Weight: 199.27002
• Product Categories: SULFONAMIDE
• Mol File: 4543-58-2.mol
• Article Data: 17

Chemical Properties

• Melting Point: 141.5-142.5 °C
• Boiling Point: 351.4°Cat760mmHg
• Flash Point: 166.3°C
• Appearance: /
• Density: 1.191g/cm³
• Vapor Pressure: 4.13E-05mmHg at 25°C
• Refractive Index: 1.547
• PKA: 10.39±0.60(Predicted)
• CAS DataBase Reference: Benzenesulfonamide, 2,4,6-trimethyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, 2,4,6-trimethyl- (9CI)(4543-58-2)
• EPA Substance Registry System: Benzenesulfonamide, 2,4,6-trimethyl- (9CI)(4543-58-2)

Safety Data

• Hazardous Substances Data: 4543-58-2(Hazardous Substances Data)

Usage

General Description

Benzenesulfonamide, 2,4,6-trimethyl- (9CI) is a chemical compound with the molecular formula C9H13NO2S. It is a member of the sulfonamide class of organic compounds and is primarily used as an intermediate in the synthesis of various pharmaceuticals and dyes. Benzenesulfonamide, 2,4,6-trimethyl- (9CI) is also known for its antimicrobial properties and is used in some agricultural and industrial applications as a biocide. Furthermore, it is known to have potential applications in the treatment of certain medical conditions, especially in combination with other drugs. Overall, benzenesulfonamide, 2,4,6-trimethyl- (9CI) is a versatile compound with a range of potential uses in various industries.

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 
• 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 
• 161452-12-6 N-(tert-butyl)-2,4,6-trimethylbenzenesulfonamide 
• 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 
• 881812-87-9 N-(mesitylenesulfonyl)-3-phenyl-1-(p-toluenesulfonyl)propylamine 
• 881812-57-3 N-(mesitylenesulfonyl)-α-(p-toluenesulfonyl)cyclooctylmethylamine 
• 881812-73-3 N-(mesitylenesulfonyl)-2-methyl-1-(p-toluenesulfonyl)propylamine 
• 881813-00-9 N-(mesitylenesulfonyl)-3-methyl-1-(p-toluenesulfonyl)butylamine 
• 1202246-67-0 N-{1-(4-fluorophenyl)ethylidene}-2,4,6-trimethylphenylsulfonamide 
• 327175-80-4 N-{1-(4-chlorophenyl)ethylidene}-2,4,6-trimethylphenylsulfonamide 
• 1202246-66-9 N-{1-(4-bromophenyl)ethylidene}-2,4,6-trimethylphenylsulfonamide 
• 1202246-73-8 N-(1-cyclohexylethylidene)-2,4,6-trimethylphenylsulfonamide 
• 1202246-70-5 N-{1-(3-bromophenyl)ethylidene}-2,4,6-trimethylphenylsulfonamide 
• 1202246-75-0 C₁₈H₁₉NO₂S 
• 327175-79-1 N-(1-phenylethylidene)-2,4,6-trimethylphenylsulfonamide 
• 1202246-65-8 N-{1-(4-methylphenyl)ethylidene}-2,4,6-trimethylphenylsulfonamide 
• 1202246-74-9 N-(1-phenylpropylidene)-2,4,6-trimethylphenylsulfonamide 

Relevant articles and documents

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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.

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.