6314-72-3

Usage

Uses

Used in Polymer Synthesis:
4-Phenylsulfamoyl-benzoic acid is used as a crosslinking agent in the synthesis of polymers, particularly in the production of epoxy resins. Its ability to form crosslinks enhances the mechanical properties and durability of the resulting polymers.
Used in Pharmaceutical Research:
4-Phenylsulfamoyl-benzoic acid has been studied for its potential anti-cancer properties. It has shown to inhibit the growth of certain tumor cells, making it a promising candidate for further research and development in oncology.
Used in Fluorescent Probe Development:
4-PHENYLSULFAMOYL-BENZOIC ACID has been utilized in the development of fluorescent probes for detecting biological molecules. Its fluorescent properties allow for the visualization and analysis of various biological processes and interactions.
Used in Dye and Pigment Production:
4-Phenylsulfamoyl-benzoic acid has also been employed in the production of dyes and pigments. Its color-producing capabilities contribute to the creation of a wide range of colors used in various industries, including textiles, paints, and plastics.

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

Upstream product

• 68-34-8 phenyl toluenesulfonamide 
• 56768-46-8 4-cyano-N-phenyl-benzenesulfonamide 
• 10130-89-9 p-carboxyphenylsulfonyl chloride 
• 62-53-3 aniline 
• 49584-26-1 p-cyanobenzenesulfonyl chloride 
• 69812-51-7 4-chlorosulfonyl-benzoic acid methyl ester 
• 138-41-0 4-(aminosulfonyl)-benzoic acid 

Downstream Products

• 114958-19-9 4-Phenylsulfamoyl-benzoyl chloride 
• 26737-96-2 N-phenyl-4-(N-phenylsulfamoyl)benzamide 

Relevant academic research and scientific papers

Identification of thiophene-benzenesulfonamide derivatives for the treatment of multidrug-resistant tuberculosis

A series of thiophene-benzenesulfonamide derivatives was designed and synthesized by exploring the structure-activity relationship of lead compounds 2,3-disubstituted thiophenes 25a and 297F as antituberculosis agents, which displayed potent antimycobacterial activity against drug-susceptible and clinically isolated drug-resistant tuberculosis. In particular, compound 17b, which had improved activity (minimum inhibitory concentration of 0.023 μg/mL) compared with the lead compounds, displayed good intracellular antimycobacterial activity in macrophages with a reduction of 1.29 log10 CFU. A druggability evaluation indicated that compound 17b had favorable hepatocyte stability, low cytotoxicity, and low hERG channel inhibition. Moreover, compound 17b exhibited modest in vivo efficacy in an acute mouse model of tuberculosis. In addition, the molecular docking study elucidated the binding mode of compound 17b in the active site of DprE1. Therefore, compound 17b may be a promising antituberculosis lead for further research.

Structure-Activity Study of Nitazoxanide Derivatives as Novel STAT3 Pathway Inhibitors

We identified nitazoxanide (NTZ) as a moderate STAT3 pathway inhibitor through immunoblot analysis and a cell-based IL-6/JAK/STAT3 pathway activation assay. A series of thiazolide derivatives were designed and synthesized to further validate the thiazolide scaffold as STAT3 inhibitors. Eight out of 25 derivatives displayed potencies greater than that of NTZ, and their STAT3 pathway inhibitory activities were found to be significantly correlated with their antiproliferative activities in HeLa cells. Derivatives 15 and 24 were observed to be more potent than the positive control WP1066, which is under phase I clinical trials. Compared with NTZ, 15 also exhibited much improved in vivo pharmacokinetic parameters in rats and efficacies against proliferations in multiple cancer cell lines, indicating a broad-spectrum effect of these thiazolides as antitumor agents targeted on STAT3.

Antibacterial Small Molecules That Potently Inhibit Staphylococcus aureus Lipoteichoic Acid Biosynthesis

The rise of antibiotic resistance, especially in Staphylococcus aureus, and the increasing death rate due to multiresistant bacteria have been well documented. The need for new chemical entities and/or the identification of novel targets for antibacterial

METHODS OF INHIBITING BACTERIAL VIRULENCE AND COMPOUNDS RELATING THERETO

The present invention relates to compounds and methods for the treatment of bacterial infections. Because their mechanism of action does not involve killing of bacteria or inhibiting their growth, the potential for these compounds to induce drug resistance in bacteria is minimized. Through inhibiting bacterial virulence, the present invention provides a novel means of treating bacterial infections.

Discovery of a type III inhibitor of LIM kinase 2 that binds in a DFG-out conformation

The first allosteric, type III inhibitor of LIM-kinase 2 (LIMK2) is reported. A series of molecules that feature both an N-phenylsulfonamide and tertiary amide were not only very potent at LIMK2 but also were extremely selective against a panel of other k

Discovery of a Type III Inhibitor of LIM Kinase 2 That Binds in a DFG-Out Conformation

The first allosteric, type III inhibitor of LIM-kinase 2 (LIMK2) is reported. A series of molecules that feature both an N-phenylsulfonamide and tertiary amide were not only very potent at LIMK2 but also were extremely selective against a panel of other k

Small-molecule inhibitors of 25-hydroxyvitamin D-24-hydroxylase (CYP24A1): Synthesis and biological evaluation

The synthesis of imidazole styrylbenzamide, tert-butyl styrylimidazole, and tert-butyl styrylsulfonate derivatives is described. Evaluation of binding affinity and inhibitory activity against CYP24A1 identified the imidazole styrylbenzamides as potent inhibitors of CYP24A1, having selectivity with respect to CYP27B1 comparable with or greater than that of the standard ketoconazole. Further evaluation of the 3,5-dimethoxy and 3,4,5-trimethoxy derivatives in chronic lymphocytic leukemia cells revealed that co-treatment of 1α,25-dihydroxyvitamin D3plus inhibitor coordinately upregulated GADD45α and CDKN1A. Docking experiments on the inhibitors in the CYP24A1 enzyme active site suggest the compounds reach the active site through the vitamin D access tunnel and are exposed to multiple hydrophobic residues. The imidazole styrylbenzamides are optimally positioned to allow interaction of the imidazole with the heme, and, in the case of the methoxy derivatives, a hydrogen bond between the 3-methoxy group and Gln82 stabilizes the molecule in a favorable active conformation.

Analgesic agents without gastric damage: Design and synthesis of structurally simple benzenesulfonanilide-type cyclooxygenase-1-selective inhibitors

In order to create novel analgesic agents without gastric disturbance, structurally simple cyclooxygenase-1 (COX-1) inhibitors with a benzenesulfonanilide skeleton were designed and synthesized. As a result, compounds 11f and 15a, which possess a p-amino group on the benzenesulfonyl moiety and p-chloro group on the anilino moiety, showed COX-1-selective inhibition. Moreover compound 11f, which is the most potent compound in this study showed more potent analgesic activity than that of aspirin at 30 mg/kg by po. The anti-inflammatory activity and gastric damage, however, were very weak or not detectably different from aspirin. Since the structure of our COX-1 inhibitors are very simple, they may be useful as lead compounds for superior COX-1 inhibitors as analgesic agents without gastric disturbance.

Inhibitors of acyl-CoA:cholesterol O-acetyltransferase (ACAT). Part 1: Identification and structure-activity relationships of a novel series of substituted N-alkyl-N-biphenylmethyl-N'-arylureas

A series of N-alkyl-N-biphenylylmethyl-N'-arylurea and related derivatives represented by 1 have been prepared and evaluated for their ability to inhibit acyl-CoA:cholesterol O-acyltransferase in vitro and to lower plasma cholesterol levels in cholesterol-fed rats in vivo. Linking of two phenyl groups via oxygen and introduction of fluorine at appropriate positions on the biphenyl moiety improved in vitro and in vivo activity. From this series of analogs, compound 40 (FR179254), which had potent in vitro potency (rabbit intestinal microsomes IC50 = 25 nM), showed excellent plasma cholesterol-lowering activity when administered via the diet (ED50 = 0.045 mg/kg). However, the hypocholesterolemic effect of this compound was moderate when dosed by oral gavage in PEG400 as a vehicle (ED50 = 5.3 mg/kg). Modification of the N'-aryl moiety led to the identification of compound 50 (FR182980) which was efficacious in both dosing models (ED50 = 0.034 mg/kg and 0.11 mg/kg, respectively).

Synthesis and Evaluation of Multisubstrate Inhibitors of an Oncogene-Encoded Tyrosine-Specific Protein Kinase. 1

The synthesis and testing of potental multisubstrate inhibitors of tyrosine-specific protein kinases are described.One of the substrates, ATP, was mimicked by the known kinase inhibitor 5'-adenosine, which was covalently linked via the sulfonyl moiety to tyrosine mimics.The resulting multisubstrate inhibitors were tested for their ability to inhibit the transfer of phosphate from ATP to a protein acceptor by p60v-abl, the tyrosine kinase encoded by the transforming gene (v-abl) of the Abelson murine leukemia virus (A-MuLV).Although the series of inhibitors displayed moderately potent activity (IC50 values as low as 19 μM), the absence of large effects produced by modification of the tyrosine mimic suggests that they do not behave as multisubstrate inhibitors but bind primarily through the adenosine moiety common to all the inhibitors.This interpretation is strengthened by the findings that the inhibitors lack specificity, inhibiting a serine kinase at compatible concentrations.