2494-79-3

Basic information

• Product Name: 4-CHLORO-3-CHLOROSULFONYLBENZOIC ACID
• Synonyms: 4-chloro-3-chlorosulfonylbenzoci acid;AKOS BBS-00007002;4-CHLORO-3-CHLOROSULFONYLBENZOIC ACID;BENZOIC ACID, 4-CHLORO-3-(CHLOROSULFONYL)-;4-chloro-3-(chlorosulphonyl)benzoic acid;3-(Chlorosulfonyl)-4-chlorobenzoic acid;4-chloro-3-(chlorosulfonyl)-;4-chloro-3-(chlorosulfonyl)benzoic acid(SALTDATA: FREE)
• CAS NO: 2494-79-3
• Molecular Formula: C₇H₄Cl₂O₄S
• Molecular Weight: 255.08
• EINECS: 219-667-6
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 2494-79-3.mol

Chemical Properties

• Melting Point: 170-172 °C
• Boiling Point: 432.4 °C at 760 mmHg
• Flash Point: 215.3 °C
• Appearance: /
• Density: 1.694 g/cm³
• Vapor Pressure: 3.03E-08mmHg at 25°C
• Refractive Index: 1.599
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Ethyl Acetate (Slightly)
• PKA: 2.77±0.10(Predicted)
• CAS DataBase Reference: 4-CHLORO-3-CHLOROSULFONYLBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-3-CHLOROSULFONYLBENZOIC ACID(2494-79-3)
• EPA Substance Registry System: 4-CHLORO-3-CHLOROSULFONYLBENZOIC ACID(2494-79-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 2494-79-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-CHLORO-3-CHLOROSULFONYLBENZOIC ACID is used as an intermediate in the synthesis of Indapamide (I500100), a medication used for treating high blood pressure and heart-related conditions. Its chemical properties allow it to be a crucial component in the development of this drug, contributing to its effectiveness in managing cardiovascular health.
Used in Agricultural Industry:
In the agricultural sector, 4-CHLORO-3-CHLOROSULFONYLBENZOIC ACID is utilized as a bactericide, helping to control and prevent bacterial infections in crops. Its ability to inhibit bacterial growth makes it a valuable asset in ensuring the health and productivity of agricultural plants.
Used in Disinfection and Sanitation:
4-CHLORO-3-CHLOROSULFONYLBENZOIC ACID also serves as a disinfectant and antiseptic, playing a vital role in maintaining cleanliness and hygiene in various settings. Its effectiveness in eliminating harmful microorganisms makes it a preferred choice for sanitizing surfaces and equipment, particularly in healthcare and food processing facilities.

InChI:InChI=1/C7H4Cl2O4S/c8-5-2-1-4(7(10)11)3-6(5)14(9,12)13/h1-3H,(H,10,11)

Upstream product

• 122-01-0 4-chloro-benzoyl chloride 
• 5216-25-1 4-chlorotrichloromethylbenzene 
• 74-11-3 para-chlorobenzoic acid 
• 7790-94-5 chlorosulfonic acid 
• 1126-46-1 Methyl 4-chlorobenzoate 

Downstream Products

• 59210-71-8 4-Chloro-3-(cyclohexyl-methyl-sulfamoyl)-benzoic acid 
• 59815-68-8 4-chloro-3-cyclooctylsulfamoylbenzoyl chloride 
• 59815-51-9 4-chloro-3-cyclohexylsulfamoyl-benzoic acid 
• 54261-57-3 4-Chloro-3-dipropylsulfamoyl-benzoic acid 
• 53604-83-4 4-chloro-3-di-n-butylsulfamoylbenzoic acid 
• 59815-50-8 3-tert.-Butylsulfamoyl-4-chlorobenzoic acid 
• 59210-68-3 4-chloro-3-diethylsulfamoyl-benzoic acid 
• 59815-52-0 4-chloro-3-o-chlorobenzylsulfamoylbenzoic acid 
• 62574-66-7 3-chlorosulfonyl-4-chlorobenzoyl chloride 
• 51522-07-7 3-methylsulphonyl-4-chlorobenzoic acid 
• 125094-59-9 2-(5-Carboxy-2-chloro-benzenesulfonyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 
• 200423-20-7 4-Chloro-3-hydroxysulfinylbenzoic acid 
• 34263-58-6 4-Amino-3-methylsulfonylbenzoesaeure 
• 404964-28-9 methyl 4-amino-3-methanesulfonylbenzoate 

Relevant articles and documents

Development of Benzenesulfonamide Derivatives as Potent Glutathione Transferase Omega-1 Inhibitors

Glutathione transferase omega-1 (GSTO1-1) is an enzyme whose function supports the activation of interleukin (IL)-1β and IL-18 that are implicated in a variety of inflammatory disease states for which small-molecule inhibitors are sought. The potent reactivity of the active-site cysteine has resulted in reported inhibitors that act by covalent labeling. In this study, structure-activity relationship (SAR) elaboration of the reported GSTO1-1 inhibitor C1-27 was undertaken. Compounds were evaluated for inhibitory activity toward purified recombinant GSTO1-1 and for indicators of target engagement in cell-based assays. As covalent inhibitors, the kinact/KI values of selected compounds were determined, as well as in vivo pharmacokinetics analysis. Cocrystal structures of key novel compounds in complex with GSTO1-1 were also solved. This study represents the first application of a biochemical assay for GSTO1-1 to determine kinact/KI values for tested inhibitors and the most extensive set of cell-based data for a GSTO1-1 inhibitor SAR series reported to date. Our research culminated in the discovery of 25, which we propose as the preferred biochemical tool to interrogate cellular responses to GSTO1-1 inhibition.

Design, synthesis, and biological evaluation of dual targeting inhibitors of histone deacetylase 6/8 and bromodomain BRPF1

Histone modifying proteins, specifically histone deacetylases (HDACs) and bromodomains, have emerged as novel promising targets for anticancer therapy. In the current work, based on available crystal structures and docking studies, we designed dual inhibitors of both HDAC6/8 and the bromodomain and PHD finger containing protein 1 (BRPF1). Biochemical and biophysical tests showed that compounds 23a,b and 37 are nanomolar inhibitors of both target proteins. Detailed structure-activity relationships were deduced for the synthesized inhibitors which were supported by extensive docking and molecular dynamics studies. Cellular testing in acute myeloid leukemia (AML) cells showed only a weak effect, most probably because of the poor permeability of the inhibitors. We also aimed to analyse the target engagement and the cellular activity of the novel inhibitors by determining the protein acetylation levels in cells by western blotting (tubulin vs histone acetylation), and by assessing their effects on various cancer cell lines.

Synthesis of a new series of 3-functionalised-1-phenyl-1,2,3-triazole sulfamoylbenzamides as carbonic anhydrase I, II, IV and IX inhibitors

The synthesis of a novel series of 3-functionalised benzenesulfonamides incorporating phenyl-1,2,3-triazole with an amide linker was achieved by using the “click-tail” approach. The new compounds, including the intermediates, were assayed as inhibitors of human carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I and II (cytosolic isoforms) and also for hCA IV and IX (transmembrane isoforms) taking acetazolamide as standard drug. Most of these compounds exhibited excellent activity against all these isoforms. hCA I was inhibited with Kis in the range of 50.8–966.8 nM, while the glaucoma associated hCA II was inhibited with Kis in the range of 6.5–760.0 nM. Isoform hCA IV was inhibited with Kis in the range of 65.3–957.5 nM, whereas the tumor associated hypoxia induced hCA IX was inhibited with Kis in the range of 30.8–815.9 nM. The structure activity relationship study for the 3-functionalised-1-phenyl-1,2,3-triazole sulfamoylbenzamides against these isoforms was also inferred from the results.

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.

AZEPANE DERIVATIVES AND METHODS OF TREATING HEPATITIS B INFECTIONS

Provided herein are compounds useful for the treatment of HBV infection in a subject in need thereof, pharmaceutical compositions thereof, and methods of inhibiting, suppressing, or preventing HBV infection in the subject.

AZEPANE DERIVATIVES AND METHODS OF TREATING HEPATITIS B INFECTIONS

Provided herein are compounds useful for the treatment of HBV infection in a subject in need thereof, pharmaceutical compositions thereof, and methods of inhibiting, suppressing, or preventing HBV infection in the subject.

HEPATITIS B ANTIVIRAL AGENTS

Provided herein are compounds useful for the treatment of HBV infection in man.

SYNTHETIC ANALOGUES OF XANTHOHUMOL

The present invention relates to novel synthetic analogues of xanthohumol and the use thereof.

Bis-Acylated Hydroxylamine Derivatives

The invention provides certain bis-acylated hydroxylamine derivative compounds, pharmaceutical compositions and kits comprising such compounds, and methods of using such compounds or pharmaceutical compositions. In particular, the invention provides methods of using such compounds or pharmaceutical compositions for treating, preventing, or delaying the onset and/or develop of a disease or condition. In some embodiments, the disease or condition is selected from cardiovascular diseases, ischemia, reperfusion injury, cancerous disease, pulmonary hypertension and conditions responsive to nitroxyl therapy.

Novel 4,4-disubstituted piperidine-based C-C chemokine receptor-5 inhibitors with high potency against human immunodeficiency virus-1 and an improved human ether-a-go-go related gene (hERG) profile

We recently described (J. Med. Chem. 2008, 51, 6538-6546) a novel class of CCR5 antagonists with strong anti-HIV potency. Herein, we detail SAR converting leads 1 and 2 to druglike molecules. The pivotal structural motif enabling this transition was the secondary sulfonamide substituent. Further finetuning of the substituent pattern in the sulfonamide paved the way to enhancing potency and bioavailability and minimizing hERG inhibition, resulting in discovery of clinical compound 122 (GSK163929).