28547-16-2

Usage

Uses

Used in Pharmaceutical Industry:
4-BENZENESULFONYLAMINOBENZOIC ACID is used as an anti-inflammatory and analgesic agent for the treatment of various inflammatory conditions such as arthritis, dysmenorrhea, and other pain-related disorders. Its ability to inhibit COX-1 and COX-2 enzymes helps in reducing inflammation and alleviating pain.
Used in Cancer Prevention:
4-BENZENESULFONYLAMINOBENZOIC ACID has shown potential as a chemopreventive agent for certain types of cancer. Its anti-inflammatory properties may contribute to the prevention of cancer development by reducing the risk factors associated with chronic inflammation.

InChI:InChI=1/C13H11NO4S/c15-13(16)10-6-8-11(9-7-10)14-19(17,18)12-4-2-1-3-5-12/h1-9,14H,(H,15,16)

Upstream product

• 150-13-0 4-amino-benzoic acid 
• 98-09-9 benzenesulfonyl chloride 
• 98-80-6 phenylboronic acid 
• 62-23-7 4-nitro-benzoic acid 
• 76883-69-7 N-(4-acetylphenyl)benzenesulfonamide 
• 98-11-3 benzenesulfonic acid 
• 94-09-7 p-aminoethylbenzoate 
• 89113-18-8 ethyl 4-benzoate 
• 107920-79-6 methyl 4-(phenylsulfonamido)benzoate 

Downstream Products

• 1258550-72-9 N-(3-nitro-4-(2-(phenylthio)ethylamino)phenylsulfonyl)-4-(phenylsulfonamido)benzamide 
• 147086-60-0 2-(p-benzenesulphonamido)phenylimidazoline 
• 1267868-88-1 2-(p-benzenesulphonamido)phenyl-1,4,5,6-tetrahydropyrimidine 
• 63421-73-8 4-Benzolsulfonamido-1-benzoylchlorid 
• 1232365-61-5 N-((2S)-1-(1-(1-hydroxy-2-(1-methyl-1H-pyrazol-3-ylamino)-2-oxoethyl)-cyclobutylamino)-3-(1-methylcycIobutyl)-1-oxopropan-2-yl)-4-(phenylsulfonamido)-benzamide 
• 878412-46-5 N-[4-(4-phenyl-piperazine-1-carbonyl)-phenyl]-benzenesulfonamide 

Relevant academic research and scientific papers

Hydroxamic acid with benzenesulfonamide: An effective scaffold for the development of broad-spectrum metallo-β-lactamase inhibitors

Given that β-lactam antibiotic resistance mediated by metallo-β-lactamases (MβLs) seriously threatens human health, we designed and synthesized nineteen hydroxamic acids with benzenesulfonamide, which exhibited broad-spectrum inhibition against four teste

Sequential C-S and S-N Coupling Approach to Sulfonamides

A one-pot three-component reaction involving nitroarenes, (hetero)arylboronic acids, and potassium pyrosulfite leading to sulfonamides was described. A broad range of sulfonamides bearing different reactive functional groups were obtained in good to excellent yields through sequential C-S and S-N coupling that does not require metal catalysts.

Convenient synthesis of novel sulfonamide derivatives as promising anticancer agents

Novel sulfonamide derivatives have been synthesized from the readily accessible N-(4-acetylphenyl)benzenesulfonamide (1). Condensation of 1 with phenylhydrazine in refluxing ethyl alcohol gave the corresponding phenylhydrazone 2, which was then added to the Vilsmeier-Haack reagent (POCl3/DMF) to give the 4-formylpyrazole derivative 3. Fusion of 1 with thiourea in the presence of iodine at 130°C afforded the 2-aminothiazole derivative 4. Refluxing 1 with an excess of N, N-dimethylformamide dimethyl acetal furnished the enaminone 5. The chemical reactivity of enaminone 5 toward some nitrogen and carbon nucleophiles has been studied to obtain polyfunctionalized heteroaromatic systems bearing a sulfonamide moiety. Besides, the enaminone 5 undergoes the Gewald reaction and reacts with ethyl cyanoacetate and elemental sulfur in the presence of morpholine to yield the 2-aminothiophene derivative 18. Moreover, the utility of 5 for the synthesis of 4-(phenylsulfonamido)benzoic acid (19) was investigated. The synthesized sulfonamides were evaluated for their in vitro cytotoxic activities against two human cell lines, MCF-7 (breast adenocarcinoma cells) and RPE-1 (normal retina pigmented epithelium cells). The results revealed that compounds 1-3, 6-8, 10, 12b, 18, 19, and 21 have a potent cytotoxic effect on MCF-7 and less on RPE-1 cells compared to the positive control doxorubicin.

Bio-potent sulfonamides

Some 4-(substituted phenylsulfonamido)benzoic acids have been synthesized by fly-ash:H3PO3 nano catalyst catalyzed condensation of substituted benzenesulfonyl chlorides and 4-aminobenzoic acid in ultrasound irradiation conditions. The yields of the sulfonamides are more than 90%. The synthesized 4-(substituted phenylsulfonamido) benzoic acid derivatives were characterized by their physical constants, analytical and spectroscopic data. Antimicrobial activities of all sulfonamides were measured by Bauer-Kirby disc diffusion method.

Method for coupling nitroaromatic compound and boric acid compound to synthesize sulfonamide compound

The invention belongs to the field of organic synthesis, and specifically discloses a method for coupling a nitroaromatic compound and a boric acid compound to synthesize a sulfonamide compound. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound comprises the steps that in an organic solvent, pyrosulfite is used as a source of SO2,and heating is carried out for a coupling reaction, and then after the post-treatment, the sulfonamide compound is obtained. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound is simple in operation, does not require nitrogen protection, and can be carried out under air. The nitroaromatic compound and the boric acid compound are abundant in source, relatively low in price, high in reaction yield, wide in applicability of a substrate and free in metal residual. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound can be used for synthesizing a series of sulfonamide compounds, and the synthesized compounds have wide application value in the fields of pesticidesand medicines.

Inhibition effect of imidazoline and hydropyrimidine derivatives on the corrosion of brass in 0.6 M aqueous sodium chloride solution

The inhibition effect of o-aminobenzoic acid (1), p-aminobenzoic acid (2), o-benzenesulphonamidobenzoic acid (3), p-benzenesulphonamidobenzoic acid (4), 2-(o-benzenesulphonamido)phenylimidazoline (5), 2-(p-benzenesulphonamido) phenylimidazoline (6), 2-(o-

Design, synthesis, and activity evaluation of broad-spectrum small-molecule inhibitors of anti-apoptotic Bcl-2 family proteins: Characteristics of broad-spectrum protein binding and its effects on anti-tumor activity

On the basis of the comparison of the structure of the Bim BH3: Bcl-x L complex and that of the ABT-737: Bcl-xL complex, a series of class A compounds were designed. These compounds had the basic skeleton of ABT-737 and the h2 residues of Bim BH3. These residues had shown themselves to be relevant to Bim BH3's broad-spectrum binding properties in saturation mutagenesis assays. Unlike ABT-737, which is a selective inhibitor of anti-apoptotic members of the Bcl-2 protein family, the class A compounds showed broad-spectrum binding activity to target proteins similar to those of Bim BH3 peptide. Then class B compounds were synthesized by modifying the structure of the most effective class A compound, A-4. Most of these class B compounds showed better binding affinity to the target proteins than the class A compounds had. They also showed themselves more effective than ABT-737 at inhibiting growth in multiple tumor cell lines known to express Bcl-x L, Bcl-2, and Mcl-1 proteins at high levels. Compounds B-11 and B-12 had the strongest anti-tumor activity of any compounds we produced. This study suggests that it is feasible to design small-molecule inhibitors based on the structure of Bim BH3, which shows broad-spectrum binding to Bcl-xL, Bcl-2, and Mcl-1 proteins. Our results also suggest that the broad-spectrum properties of small-molecule inhibitors binding to target proteins play a critical role in inhibiting the growth of many tumor cells. Finally, our study provides a series of lead compounds that merit further research into anti-cancer therapeutics.

SULFONAMIDE COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF

Compounds are provided according to formula (1), wherein W, X, Z, R1, R2, R3, and ml are as defined herein. Provided compounds and pharmaceutical compositions thereof are useful for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non- limiting example, pain, inflammation, cognitive disorders, anxiety, depression, and others. Provided compounds and pharmaceutical compositions thereof are also useful for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non- limiting example immune-mediated disorders and autoimmune diseases, including multiple sclerosis, type-1 diabetes mellitus, type-2 diabetes mellitus, rheumatoid arthritis, psoriasis, contact dermatitis, obesity, systemic lupus erythematosus, graft-versus host disease, transplant rejection, and others.

NOVEL COMPOUNDS, PHARMACEUTICAL COMPOSITIONS CONTAINING SAME, METHODS OF USE FOR SAME, AND METHODS FOR PREPARING SAME

The present invention relates to a novel class of compounds comprising formula I, wherein n is 0 or 1. A is NR1, O, or S, wherein R1 is H, hydroxyl, C1-C10 alkyl, C1-C10 alkoxy, alkenyl, aryl, alkylaryl or arylalkyl. X is a carboxylate, a phosphonate, or a phosphate residue, or a C1-C10 alkyl residue optionally substituted with a carboxylate, phosphonate or phosphate residue. Y is a C1-C20 alkyl, alkenyl, halide, hydroxyl, C1-C20 alkoxy, aryl, alkylaryl, arylalkyl, cycloalkyl, cycloalkenyl, or a heterocyclic ring and is optionally substituted with one or more halides. Z is a H, a hydroxyl group, a halide, an aryl group, an alkylaryl group, an arylalkyl group, a cycloalkyl group, a cycloalkenyl group or a heterocyclic ring and is optionally substituted with one or more C1-C10 alkyl groups, C1-C10alkoxy groups, hydroxyl groups, cyano groups, carboxylate groups, halides, aryl groups, alkylaryl groups, arylalkyl groups, cycloalkyl groups, cycloalkenyl groups or heterocyclic rings.

Design and synthesis of small molecule glycerol 3-phosphate acyltransferase inhibitors

The incidence of obesity and other diseases associated with an increased triacylglycerol mass is growing rapidly, particularly in the United States. Glycerol 3-phosphate acyltransferase (GPAT) catalyzes the ratelimiting step of glycerolipid biosynthesis, the acylation of glycerol 3-phosphate with saturated long-chain acyl-CoAs. In an effort to produce small molecule inhibitors of this enzyme, a series of benzoic and phosphonic acids was designed and synthesized. In vitro testing of this series has led to the identification of several compounds, in particular 2-(nonylsulfonamido)benzoic acid (15g), possessing moderate GPAT inhibitory activity in an intact mitochondrial assay.