3740-18-9

Usage

Uses

Used in Organic Chemistry Research:
2,4-Dichloro-5-(chlorosulphonyl)benzoic acid is used as a sulfonylating agent for the synthesis of complex organic compounds. Its unique chemical structure enables it to participate in various reactions, making it a valuable tool in the field of organic chemistry.
Used in Industrial Applications:
In industrial settings, 2,4-Dichloro-5-(chlorosulphonyl)benzoic acid is used as a key intermediate in the production of certain chemicals and pharmaceuticals. Its versatility in chemical reactions allows for the creation of a wide range of products, contributing to the efficiency and effectiveness of industrial processes.
Used in Pharmaceutical Synthesis:
2,4-Dichloro-5-(chlorosulphonyl)benzoic acid is used as a building block in the synthesis of various pharmaceutical compounds. Its ability to participate in multiple chemical reactions makes it an essential component in the development of new drugs and medications.

InChI:InChI=1/C7H3Cl3O4S/c8-4-2-5(9)6(15(10,13)14)1-3(4)7(11)12/h1-2H,(H,11,12)

Upstream product

• 50-84-0 2,4 dichlorobenzoic acid 
• 7790-94-5 chlorosulfonic acid 

Downstream Products

• 103539-64-6 γ-(5-Carboxy-2,4-dichlorophenylsulfonamido)butyric acid 
• 51521-74-5 2,4-dichloro-5-carboxybenzenesulfinic acid 
• 89894-62-2 2,4-dichloro-5-chlorosulfonylbenzoic acid N-methylamide 
• 1449428-77-6 ClH*C₁₉H₁₈Cl₂N₄O₄S₂ 
• 1449428-76-5 2,4-dichloro-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-5-((4-hydroxypiperidin-1-yl)sulfonyl)benzamide 
• 1449428-75-4 1-((2,4-dichloro-5-((3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)carbamoyl)phenyl)sulfonyl)piperidine-4-carboxylic acid 
• 1449428-74-3 1-(2,4-dichloro-5-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylcarbamoyl)phenylsulfonyl) piperidine-3-carboxylic acid 
• 1449428-73-2 2,4-dichloro-N-(3-cyano-6-(4-nitrophenyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-5-(morpholinosulfonyl)benzamide 
• 1449428-72-1 2,4-dichloro-N-(3-cyano-6-(4-cyanophenyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-5-(morpholinosulfonyl)benzamide 
• 1449428-71-0 ethyl 4-(3-cyano-2-(2,4-dichloro-5-(morpholinosulfonyl)benzamido)-4,5-dihydrothieno[2,3-c]pyridin-6(7H)-yl)benzoate 
• 1449428-70-9 2,4-dichloro-N-(3-cyano-6-(4-methoxyphenyl)-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-5-(morpholinosulfonyl)benzamide 
• 1449428-69-6 4-(3-cyano-2-(2,4-dichloro-5-(morpholinosulfonyl)benzamido)-4,5,6,7-tetrahydrobenzo[b]thiophen-6-yl)phenyl acetate 
• 1449428-68-5 tert-butyl 3-cyano-2-(2,4-dichloro-5-(morpholinosulfonyl)benzamido)-4,5-dihydrothieno[2,3-c]pyridine-6(7H)-carboxylate 
• 1449428-67-4 2,4-dichloro-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-5-(4-methylpiperidin-1-ylsulfonyl)benzamide 

Relevant academic research and scientific papers

2,4-Dichloro-5-[(N-aryl/alkyl)sulfamoyl]benzoic acid derivatives: In vitro antidiabetic activity, molecular modeling and in silico ADMET screening

Background: Postprandial hyperglycemia can be reduced by inhibiting major carbohydrate hydrolyzing enzymes, such as α-glucosidase and α-amylase which is an effective approach in both preventing and treating diabetes. Objective: The aim of this study was to synthesize a series of 2,4-dichloro-5-[(N-aryl/alkyl)sulfamoyl] benzoic acid derivatives and evaluate α-glucosidase and α-amylase inhibitory activity along with molecular docking and in silico ADMET property analysis. Method: Chlorosulfonation of 2,4-dichloro benzoic acid followed by reaction with corresponding anilines/amines yielded 2,4-dichloro-5-[(N-aryl/alkyl)sulfamoyl]benzoic acid derivatives. For evaluating their antidiabetic potential α-glucosidase and a-amylase inhibitory assays were carried out. In silico molecular docking studies of these compounds were performed with respect to these enzymes and a computational study was also carried out to predict the drug-likeness and ADMET properties of the title compounds. Results: Compound 3c (2,4-dichloro-5-[(2-nitrophenyl)sulfamoyl]benzoic acid) was found to be highly active having 3 fold inhibitory potential against α-amylase and 5 times inhibitory activity against a-glucosidase in comparison to standard drug acarbose. Conclusion: Most of the synthesized compounds were highly potent or equipotent to standard drug acarbose for inhibitory potential against α-glucosidase and α-amylase enzyme and hence this may indicate their antidiabetic activity. The docking study revealed that these compounds interact with active site of enzyme through hydrogen bonding and different pi interactions.

Highly Potent Non-Carboxylic Acid Autotaxin Inhibitors Reduce Melanoma Metastasis and Chemotherapeutic Resistance of Breast Cancer Stem Cells

Autotaxin (ATX, aka. ENPP2) is the main source of the lipid mediator lysophosphatidic acid (LPA) in biological fluids. This study reports on inhibitors of ATX derived by lead optimization of the benzene-sulfonamide in silico hit compound 3. The new analogues provide a comprehensive structure-activity relationship of the benzene-sulfonamide scaffold that yielded a series of highly potent ATX inhibitors. The three most potent analogues (3a, IC50 ～ 32 nM; 3b, IC50 ～ 9 nM; and 14, IC50 ～ 35 nM) inhibit ATX-dependent invasion of A2058 human melanoma cells in vitro. Two of the most potent compounds, 3b and 3f (IC50 ～ 84 nM), lack inhibitory action on ENPP6 and ENPP7 but possess weak antagonist action specific to the LPA1 G protein-coupled receptor. In particular, compound 3b potently reduced in vitro chemotherapeutic resistance of 4T1 breast cancer stem-like cells to paclitaxel and significantly reduced B16 melanoma metastasis in vivo.

AUTOTAXIN INHIBITORS

The present disclosure provides novel ATX inhibitors, and pharmaceutical compositions comprising said inhibitors, as well as methods of treatment comprising administration of said inhibitors.

Structure-activity relationships of new cyanothiophene inhibitors of the essential peptidoglycan biosynthesis enzyme MurF

Peptidoglycan is an essential component of the bacterial cell wall, and enzymes involved in its biosynthesis represent validated targets for antibacterial drug discovery. MurF catalyzes the final intracellular peptidoglycan biosynthesis step: the addition of D-Ala-D-Ala to the nucleotide precursor UDP-MurNAc-L-Ala-γ-D-Glu-meso-DAP (or L-Lys). As MurF has no human counterpart, it represents an attractive target for the development of new antibacterial drugs. Using recently published cyanothiophene inhibitors of MurF from Streptococcus pneumoniae as a starting point, we designed and synthesized a series of structurally related derivatives and investigated their inhibition of MurF enzymes from different bacterial species. Systematic structural modifications of the parent compounds resulted in a series of nanomolar inhibitors of MurF from S. pneumoniae and micromolar inhibitors of MurF from Escherichia coli and Staphylococcus aureus. Some of the inhibitors also show antibacterial activity against S. pneumoniae R6. These findings, together with two new co-crystal structures, represent an excellent starting point for further optimization toward effective novel antibacterials.

Synthesis of n-methyl-3-carboxy-2-chloro-dibenzo[c,f][1,4,5]oxa-thiazepine s,s-dioxide and its derivatives

A new dibenzo-condensed oxathiazepinecarboxylic acid was obtained starting from the methyl ester of 2,4-dichloro-5-chlorosulfonylbenzoic acid. Derivatives were obtained from N-phenylamide and N-methylamide of 2,4-dichloro-5- chlorosulfonylbenzoic acid. Methods for the preparation of the starting aromatic sulfonyl chlorides were proposed.

THERAPEUTIC COMPOUNDS

The present invention provides novel compounds that function as potentiators of glutamate receptors, methods for their preparation, pharmaceutical compositions containing them, and methods of their use in therapy.

(2-methyl-5-(methylsulfonyl)benzoyl)guanidine Na+/H+ antiporter inhibitors

The inhibition of the Na+/H+ exchanger during cardiac ischemia and reperfusion has been shown to be beneficial for the preservation of the cellular integrity and functional performance. The aim of the present investigation was to come up with potent and selective benzoylguanidines as NHE inhibitors for their use as an adjunctive therapy in the treatment of acute myocardial infarction. During the course of our investigations it became clear that the substitution ortho to the acylguanidine was of crucial importance for the potency of the compounds. 4-Chloro and 4-fluoro-2- methylbenzoic acids 6 and 7 were prepared using the directed ortho metalation technique with the carboxylic acid as the directing group. With the LDA/methyl iodide system the 2-methyl group could be extended to an ethyl group. 4-Alkyl groups were inserted by the palladium-catalyzed cross-coupling reaction into the 4-bromo-2-methylbenzoic acid methyl ester (20). Starting with benzoic acids 6-19, the methylsulfonyl group was introduced by a sequence of standard reactions (sulfochlorination, reduction, and methylation). 4-Aryl derivatives 6875 were synthesized by the palladium- catalyzed Suzuki reaction. A large number of nucleophilic displacement reactions in the 4-position were carried out with S-, O-, and N-nucleophiles as well as with the cyano and trifluoromethyl group. Using the ester method, acid chlorides, or Mukaiyama's procedure, the 5-(methylsulfonyl)benzoic acid derivatives were finally converted to the (5- (methylsulfonyl)benzoyl)guanidines 165-267 with excessive guanidine. In some cases nucleophilic substitutions with pyridinols and piperidine derivatives were carried out at the end of the reaction sequence with the 4-halo-N- (diaminomethylene)-5-(methylsulfonyl)benzamides. Variations in the 4-position were most reasonable, but the volume of the substituents was of crucial importance. Substitution in the 3- and particularly in the 6-position led to considerable worsening of the inhibitory effects of the Na+/H+ exchanger. The 2-methyl compounds, however, showed without exception higher in vitro activities than their respective demethyl counterparts as they are exemplified by the reference compounds 266 and 267, obviously caused by a conformational restriction of the acylguanidine chain. The development compound (2-methyl-5-(methylsulfonyl)-4-pyrrolobenzoyl)guanidine, methanesulfonate (246) is a NHE-1 subtype specific NHE inhibitor, being 27- fold more potent toward the NHE-1 than the NHE-2 isoform, 246 was found to act cardioprotectively not only when given before an experimentally induced ischemia, but also curatively after the onset of symptoms of acute myocardial infarction when given prior to the induction of reperfusion.