5317-87-3

Usage

Uses

Used in Pharmaceutical Industry:
N-(3-acetylphenyl)-4-methylbenzenesulfonamide is used as a pharmaceutical intermediate for the synthesis of potential drug candidates. Its ability to inhibit the growth of microorganisms makes it a valuable component in the development of new antimicrobial agents.
Used in Medical Treatments:
Due to its anti-inflammatory and analgesic properties, N-(3-acetylphenyl)-4-methylbenzenesulfonamide is used as a potential candidate for the treatment of various medical conditions that require relief from inflammation and pain. Its multifaceted therapeutic potential makes it a promising compound for further research and development in the medical field.

Upstream product

• 99-03-6 1-(3-aminophenyl)ethanone 
• 98-59-9 p-toluenesulfonyl chloride 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 121-89-1 3-Nitroacetophenone 

Downstream Products

• 1477503-65-3 4-methyl-N-(3-(6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)phenyl)benzenesulfonamide 

Relevant academic research and scientific papers

Straightforward and Sustainable Synthesis of Sulfonamides in Water under Mild Conditions

Ideally, a sustainable chemical synthesis should involve the use of non-toxic solvents and reactants, easy separations and purification by energy-efficient processes. In this context, reconsidering the synthesis of widely used drugs is especially timely and should allow important benefits to be obtained in terms of environmental impact. Sulfonamides are pertinent as their synthesis generally requires the use of toxic and/or hard-to-remove solvents such as dichloromethane, DMF and DMSO. In addition, toxic and highly reactive sulfur-containing sources such as sulfonyl chloride are often involved and coupled with amines. Moreover, the latter may exhibit some toxicity and are generally difficult to purify. Herein, we disclose the unprecedented and sustainable synthesis of sulfonamides by using sodium sulfinate as a commercial and stable sulfur source and nitroarenes as the nitrogen-containing reactant. In addition, under the optimized conditions only water is used as a “green” solvent and the products are collected by simple filtration.

Iron-catalyzed N -arylsulfonamide formation through directly using nitroarenes as nitrogen sources

One-step, catalytic synthesis of N-arylsulfonamides via the construction of N-S bonds from the direct coupling of sodium arylsulfinates with nitroarenes was realized in the presence of FeCl2 and NaHSO3 under mild conditions. In this process, stable and readily available nitroarenes were used as nitrogen sources, and NaHSO3 acted as a reductant to provide N-arylsulfonamides in good to excellent yields. A broad range of functional groups were very well-tolerated in this reaction system. In addition, mechanistic studies indicated that the N-S bond might be generated through direct coupling of nitroarene with sodium arylsulfinate prior to the reduction of nitroarenes by NaHSO3. Accordingly, a reaction mechanism involving N-aryl-N-arenesulfonylhydroxylamine as an intermediate was proposed.

Synthesis and biological evaluation of glucagon-like peptide-1 receptor agonists

In this study, a series of fused-heterocyclic derivatives were systematically designed and synthesized using an efficient route, and evaluated in terms of GLP-1R agonist activity. We employed short synthetic steps and reactions that are tolerant of the presence of various functional groups and suitable for parallel operations to enable the rapid generation of libraries of diverse and structurally complex small molecules. Of the compounds synthesized, 3-(8-chloro-6-(trifluoromethyl)imidazo[1,2-a] pyridin-2-yl)phenyl methanesulfonate (8e) was the most potent agonist with an EC50 of 7.89 μM, and thus is the compound with the greatest potential for application. These findings represent a valuable starting point for the design and discovery of small-molecule GLP-1R agonists that can be administered orally.

Sulfonamide chalcone as a new class of α-glucosidase inhibitors

Chalcones 1-20, a new class of glycosidase inhibitors, were synthesized, and their glycosidase inhibitory activities were investigated. Non-aminochalcones 1-12 had no inhibitory activity, however, aminochalcones 13-20 had strong glycosidase (α-glucosidase, α-amylase, and β-amylase) inhibitory activities. In particular, sulfonamide chalcones 17-20 had more potent α-glucosidase inhibitory activity than aminated chalcone 13-16. 4′-(p-Toluenesulfonamide)-3,4-dihydroxy chalcone 20 (IC50 = 0.4 μM) was the best inhibitor against α-glucosidase, and these sulfonamide chalcones showed non-competitive inhibition.