2548-29-0

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
3-chlorosulfonyl-4-methyl-benzoic acid is utilized as a key intermediate in the synthesis of pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides due to its unique chemical structure and reactivity.
Used in Dye and Pigment Production:
In the dye and pigment industry, 3-chlorosulfonyl-4-methyl-benzoic acid is employed for the production of various dyes and pigments, leveraging its chemical properties to create a range of colorants for different applications.
Used in Materials Science:
3-chlorosulfonyl-4-methyl-benzoic acid has potential applications in the field of materials science, particularly in the development of specialty polymers and coatings. Its functional groups and aromatic structure allow for the creation of materials with tailored properties, enhancing performance in specific applications.
Used in the Development of Specialty Polymers and Coatings:
As a component in the development of specialty polymers and coatings, 3-chlorosulfonyl-4-methyl-benzoic acid is used to impart specific characteristics such as durability, resistance to environmental factors, and unique optical or electronic properties, making it valuable in high-performance material formulations.

InChI:InChI=1/C8H7ClO4S/c1-5-2-3-6(8(10)11)4-7(5)14(9,12)13/h2-4H,1H3,(H,10,11)

Upstream product

• 874-60-2 4-methyl-benzoyl chloride 
• 99-94-5 p-Toluic acid 
• 99-75-2 4-methyl-benzoic acid methyl ester 

Downstream Products

• 20532-05-2 4-methyl-3-sulfamoylbenzoic acid 
• 300383-08-8 4-methyl-3-(morpholine-4-sulfonyl)-benzoic acid 
• 651728-83-5 3-chlorosulfonyl-4-methylbenzoic acid 2-(p-tolylsulfonyl)ethyl ester 
• 547739-67-3 3-chlorosulfonyl-4-methylbenzoic acid chloride 
• 1313391-08-0 C₂₅H₂₅F₂N₃O₄S 
• 104941-65-3 4-methyl-3-(N-(p-tolyl)sulfamoyl)benzoic acid 
• 406927-72-8 C₁₅H₁₅NO₄S 
• 325721-47-9 C₁₅H₁₅NO₅S 
• 1050918-04-1 C₁₅H₁₅NO₅S 
• 1036436-17-5 3-(N-(4-chlorophenyl)sulfamoyl)-4-methylbenzoic acid 
• 438021-88-6 C₁₄H₁₂ClNO₄S 
• 379729-09-6 C₁₄H₁₂FNO₄S 
• 353468-24-3 C₁₄H₁₂FNO₄S 
• 1031192-78-5 C₁₅H₁₂F₃NO₄S 

Relevant academic research and scientific papers

3-Functionalised benzenesulphonamide based 1,3,4-oxadiazoles as selective carbonic anhydrase XIII inhibitors: Design, synthesis and biological evaluation

A new series of benzenesulphonamide linked-1,3,4-oxadiazole hybrids (6a–s) has been synthesized and tested for their carbonic anhydrase inhibition against human (h) carbonic anhydrase (CA) isoforms hCA I, II, IX, and XIII. Fluorescence properties of some of the synthesized molecules were studied. Most of the molecules exhibited significant inhibitory power, comparable or better than the standard drug acetazolamide (AAZ) on hCA XIII. Out of 19 tested molecules, compound 6e (75.8 nM) was 3 times more potent than AAZ (250.0 nM) against hCA I, whereas compound 6e (15.4 nM), 6g (16.2 nM), 6h (16.4 nM) and 6i (17.0 nM) were found to be more potent than AAZ (17.0 nM) against isoform hCA XIII. It is anticipated that these compounds could be taken as the potential leads for the development of selective hCA XIII isoform inhibitors with improved potency.

Design and synthesis of benzenesulfonamide-linked imidazo[2,1-b][1,3,4]thiadiazole derivatives as carbonic anhydrase I and II inhibitors

A novel series of imidazothiadiazole-linked benzenesulfonamide derivatives (5a–t) was synthesized and subjected for screening against the four physiologically and pharmacologically relevant human carbonic anhydrase (hCA) isoforms: hCA I, II, VA, and IX. The compounds selectively inhibited hCA I and II over hCA VA and IX. Furthermore, among the two cytosolic isoforms, hCA II was more effectively inhibited as compared with hCA I. The most active compounds were 5o with Ki = 0.246 μM and 5p with Ki = 0.376 μM against hCA II, whereas compound 5f showed good inhibition against both hCA I and II with Ki = 0.493 and 0.4 μM, respectively. This class of underexplored sulfonamides may be used to design isoform-selective CA inhibitors targeting enzymes of medicinal chemistry interest.

Synthesis, 3D-structure and stability analyses of NRPa-308, a new promising anti-cancer agent

We report herein the synthesis of a newly described anti-cancer agent, NRPa-308. This compound antagonizes Neuropilin-1, a multi-partners transmembrane receptor overexpressed in numerous tumors, and thereby validated as promising target in oncology. The p

Synthesis and Biological Evaluation of 4-Sulfamoylphenyl/Sulfocoumarin Carboxamides as Selective Inhibitors of Carbonic Anhydrase Isoforms hCA II, IX, and XII

With the aim to develop potent and selective human carbonic anhydrase inhibitors (hCAIs), we synthesized 4-sulfamoylphenyl/sulfocoumarin benzamides (series 5 a–r and series 7 a–q) and evaluated their inhibition profiles against five isoforms of the zinc-containing human carbonic anhydrase (hCA, EC 4.2.1.1): cytosolic hCA I and II, and the transmembrane isozymes hCA IV, IX, and XII. Compounds 5 a–r were found to selectively inhibit hCA II in the nanomolar range, while being less effective against the other hCA isoforms. As noted from the literature, sulfocoumarin (1,2-benzoxathiine 2,2-dioxide) acts as a “prodrug” inhibitor and is hydrolyzed by the esterase activity of hCA to form 2-hydroxyphenylvinylsulfonic acid, which thereafter binds to the enzyme in a manner similar to that of coumarins and sulfoxocoumarins. All these sulfocoumarins (compounds 7 a–q) were found to be very weak or ineffective as inhibitors of the housekeeping off-target hCA isoforms I and II, and effectively inhibited the transmembrane tumor-associated isoforms IX and XII in the high nanomolar to micromolar ranges. Further structural modifications of these molecules could be useful for the development of effective hCA inhibitors used for the treatment of glaucoma, epilepsy, and cancer.

Identification and Optimization of Anthranilic Acid Based Inhibitors of Replication Protein A

Replication protein A (RPA) is an essential single-stranded DNA (ssDNA)-binding protein that initiates the DNA damage response pathway through protein-protein interactions (PPIs) mediated by its 70N domain. The identification and use of chemical probes that can specifically disrupt these interactions is important for validating RPA as a cancer target. A high-throughput screen (HTS) to identify new chemical entities was conducted, and 90 hit compounds were identified. From these initial hits, an anthranilic acid based series was optimized by using a structure-guided iterative medicinal chemistry approach to yield a cell-penetrant compound that binds to RPA70N with an affinity of 812 nm. This compound, 2-(3- (N-(3,4-dichlorophenyl)sulfamoyl)-4-methylbenzamido)benzoic acid (20 c), is capable of inhibiting PPIs mediated by this domain.

Structure optimization of 2-benzamidobenzoic acids as PqsD inhibitors for Pseudomonas aeruginosa infections and elucidation of binding mode by SPR, STD NMR, and molecular docking

Pseudomonas aeruginosa employs a characteristic pqs quorum sensing (QS) system that functions via the signal molecules PQS and its precursor HHQ. They control the production of a number of virulence factors and biofilm formation. Recently, we have shown that sulfonamide substituted 2-benzamidobenzoic acids, which are known FabH inhibitors, are also able to inhibit PqsD, the enzyme catalyzing the last and key step in the biosynthesis of HHQ. Here, we describe the further optimization and characterization of this class of compounds as PqsD inhibitors. Structural modifications showed that both the carboxylic acid ortho to the amide and 3′-sulfonamide are essential for binding. Introduction of substituents in the anthranilic part of the molecule resulted in compounds with IC50 values in the low micromolar range. Binding mode investigations by SPR with wild-type and mutated PqsD revealed that this compound class does not bind into the active center of PqsD but in the ACoA channel, preventing the substrate from accessing the active site. This binding mode was further confirmed by docking studies and STD NMR.

Synthesis, characterization and antimicrobial activity of bifunctional sulfonamide-amide derivatives

A convenient synthesis of bifunctional sulfonamide-amide derivatives was reported. Amide coupling of 4-methyl benzoic acid 1 followed by reaction with chlorosulfonic acid produce ethyl-4-(3-(chlorosulfonyl)-4-methylbenzoyl) piperazine-1-carboxylate 4. The

Novel pyrazolo[1,5-a]pyridines as p110α-selective PI3 kinase inhibitors: Exploring the benzenesulfonohydrazide SAR

Structure-activity relationship studies of the pyrazolo[1,5-a]pyridine class of PI3 kinase inhibitors show that substitution off the hydrazone nitrogen and replacement of the sulfonyl both gave a loss of p110α selectivity, with the exception of an N-hydroxyethyl analogue. Limited substitutions were tolerated around the phenyl ring; in particular the 2,5-substitution pattern was important for PI3 kinase activity. The N-hydroxyethyl compound also showed good inhibition of cell proliferation and inhibition of phosphorylation of Akt/PKB, a downstream marker of PI3 kinase activity. It had suitable pharmacokinetics for evaluation in vivo, and showed tumour growth inhibition in two human tumour cell lines in xenograft studies. This work has provided suggestions for the design of more soluble analogues.

AMIDE COMPOUNDS, COMPOSITIONS AND USES THEREOF

Compounds are provided according to formula (1 ) : where A, B, W, X', L, R1, R3, R4b, and m' 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.

ARYLSULFONAMIDE-BASED MATRIX METALLOPROTEASE INHIBITORS

The present invention provides a compound of formula (I):said compound is inhibitor of MMP-2, and/or MMP-8, and/or MMP-9, and/or MMP-12 and/or MMP-13, and thus can be employed for the treatment of a disorder or disease characterized by abnormal activity of MMP-2, and/or MMP-8, and/or MMP-9, and/or MMP-12 and/or MMP- 13. Accordingly, the compound of formula (I) can be used in treatment of disorders or diseases mediated by MMP-2, and/or MMP-8, and/or MMP-9, and/or MMP-12, and/or MMP- 13. Finally, the present invention also provides a pharmaceutical composition.