58734-57-9

Usage

Uses

Used in Pharmaceutical Industry:
Benzenesulfonamide, 3-methoxy(9CI) is used as an active pharmaceutical ingredient for the development of antibiotics. Its antibacterial properties make it a valuable component in the formulation of medications designed to combat bacterial infections.
Used in Medical Research:
Benzenesulfonamide, 3-methoxy(9CI) is used as a research compound in the study of sulfonamide-based drugs. It aids in understanding the structure-activity relationships and the mechanism of action of sulfonamides, which can lead to the development of new and improved antibacterial agents.
Used in Industrial Applications:
Benzenesulfonamide, 3-methoxy(9CI) is used as a chemical intermediate in the synthesis of various industrial products. Its versatility in chemical reactions allows it to be a key component in the production of dyes, pigments, and other specialty chemicals.

InChI:InChI=1/C7H9NO3S/c1-11-6-3-2-4-7(5-6)12(8,9)10/h2-5H,1H3,(H2,8,9,10)

Upstream product

• 1392407-90-7 C₁₀H₁₄N₂O₃S 
• 766-85-8 3-methoxy-1-iodobenzene 
• 536-90-3 m-Anisidine 
• 10130-74-2 m-Methoxybenzenesulfonyl chloride 

Downstream Products

• 93139-28-7 1-(3-Methoxy-benzolsulfonyl)-3-butyl-harnstoff 
• 1187953-16-7 N-benzyl-3-methoxybenzenesulfonamide 
• 1254305-94-6 C₁₆H₁₁ClF₃N₃O₄S 
• 1425038-92-1 3-methoxybenzenesulfonyl azide 
• 1410782-64-7 3-methoxy-N-(3-methyl-2-oxo-1,2,3,4-tetrahydro-quinazolin-6-yl)benzenesulfonamide 
• 1219741-35-1 N-[(3-methoxyphenyl)sulfonyl]acetamide 
• 102607-90-9 N-([(4-chlorophenyl)amino]carbonyl)-3-methoxybenzenesulfonamide 

Relevant academic research and scientific papers

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.

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.

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.

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.

Palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides: Scope of the three-component synthesis of N-aminosulfonamides

By using DABCO·(SO2)2, DABSO, as a solid bench-stable SO2-equivalent, the palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides has been achieved. N,N-Dialkylhydrazines are employed as the N-nucleophiles and provide N-aminosulfonamides as the products in good to excellent yields. The reactions are operationally simple to perform, requiring only a slight excess of SO 2 (1.2-2.2 equiv.), and tolerate a variety of substituents on the halide coupling partner. Variation of the hydrazine component is also demonstrated. The use of N,N-dibenzylhydrazine as the N-nucleophile delivers N-aminosulfonamide products that can be converted into the corresponding primary sulfonamides using a high-yielding, telescoped, deprotection sequence. The ability to employ hydrazine·SO2 complexes as both the N-nucleophile and SO2 source is also illustrated.

Acyl sulfonamide anti-proliferatives: Benzene substituent structure-activity relationships for a novel class of antitumor agents

Two closely related diaryl acylsulfonamides were recently reported as potent antitumor agents against a broad spectrum of human tumor xenografts (colon, lung, breast, ovary, and prostate) in nude mice. Especially intriguing was their activity against colorectal cancer xenografts. In this paper, rapid parallel synthesis along with traditional medicinal chemistry techniques were used to quickly delineate the structure-activity relationships of the substitution patterns in both phenyl rings of the acylsufonamide anti-proliferative scaffold. Although the molecular target of the compounds remains unclear, we determined that the vascular endothelial growth factor-dependent human umbilical vein endothelial cells assay in combination with a soft agar disk diffusion assay allowed for optimization of potency in the series. The pharmacokinetic properties and in vivo activity in an HCT116 xenograft model are reported for representative compounds.

DISSOCIATION OF SUBSTITUTED BENZENESULPHONAMIDES IN WATER, METHANOL AND ETHANOL

Thirteen monosubstituted arylsulphonamides (XC6H4SO2NH2) and two 3,4-disubstituted arylsulphonamides (X2C6H3SO2NH2) have been synthetized and their dissociation constants have been measured by potentiometric titration in water, methanol, and ethanol.The Hammett substitution dependences have been calculated for all the media, and changes in the reaction constants due to transition from water to alcohols are discussed in confrontation with analogous dependences of benzoic acids.The reaction constant ρ found in methanol is lower than that in water.The dissociation constants have been treated by the method of the principal components and by multiple linear regression.