22808-73-7

Usage

Uses

Used in Organic Synthesis:
Methyl 4-sulphamoylbenzoate is used as a key intermediate in the synthesis of various organic compounds for different applications. Its unique chemical structure allows it to be a versatile building block in the creation of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, methyl 4-sulphamoylbenzoate is used as a starting material for the development of new drugs. Its sulphonyl amide group can be modified to create a range of bioactive molecules with potential therapeutic properties.
Used in Agrochemical Industry:
Methyl 4-sulphamoylbenzoate is also utilized in the agrochemical sector for the synthesis of new pesticides and herbicides. Its chemical properties make it suitable for the development of compounds that can effectively control pests and weeds in agricultural settings.
Used in Specialty Chemicals:
In the specialty chemicals market, methyl 4-sulphamoylbenzoate is employed as a precursor for the production of various high-value chemicals. Its unique structure can be tailored to create compounds with specific properties, such as UV stabilizers, dyes, and other performance-enhancing additives.

InChI:InChI=1/C8H9NO4S/c1-13-8(10)6-2-4-7(5-3-6)14(9,11)12/h2-5H,1H3,(H2,9,11,12)

Upstream product

• 186581-53-3 diazomethane 
• 138-41-0 4-(aminosulfonyl)-benzoic acid 
• 67-56-1 methanol 
• 110955-54-9 4-Isopropylidenesulfamoyl-benzoic acid methyl ester 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 70-55-3 toluene-4-sulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 155495-85-5 N-(benzylidene)-4-(methoxycarbonyl)benzenesulfonamide 
• 128924-56-1 C₁₅H₁₃ClN₂O₅S 
• 89820-24-6 N-(α-methylbenzyl)-4-methoxycarbonylbenzenesulfonamide 
• 105899-96-5 N-<(p-carbomethoxyphenyl)sulfonyl>-P,P,P-triphenylphospha-λ⁵-azene 
• 88241-94-5 methyl 4-butylaminocarbonylaminosulfonylbenzoate 
• 35264-29-0 4-(hydrazinecarbonyl)benzene-1-sulfonamide 
• 768387-53-7 4-(di-prop-2-ynyl-sulfamoyl)-benzoic acid methyl ester 
• 648869-34-5 4-(4-oxo-2-m-tolyl-pentanoylsulfamoyl)-benzoic acid methyl ester 
• 67472-44-0 4-(hydroxymethyl)benzenesulfonamide 
• 1580456-62-7 2-[4-(aminosulfonyl)benzoyl]-N-[4-(aminosulfonyl)phenyl]-1-hydrazinecarbothioamide 
• 1580456-51-4 4-{3-[4-(aminosulfonyl)phenyl]-5-thioxo-1,5-dihydro-4H-1,2,4-triazol-4-yl}benzenesulfonamide 
• 1580456-69-4 C₈H₈N₃O₃S₃^(1-)*K⁽¹⁺⁾ 
• 1580456-71-8 4-(4-amino-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)benzenesulfonamide 
• 1580456-73-0 4-(4-amino-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-N-[(Z)-(dimethylamino)methylidene]benzenesulfonamide 

Relevant academic research and scientific papers

Novel benzenesulfonamides aryl and arylsulfone conjugates adopting tail/dual tail approaches: Synthesis, carbonic anhydrase inhibitory activity and molecular modeling studies

New series of benzenesulfonamide and benzoic acid derivatives were designed and synthesized using tail/dual tail approach to improve potency and selectivity as carbonic anhydrase inhibitors. The synthesized compounds evaluated as CAIs against isoforms hCA I, II, IV and IX with acetazolamide (AAZ) as standard inhibitor. The benzenesulfonamide derivatives 7a-d, 8a-h, 12a-c, 13a and 15a-c showed moderate to potent inhibitory activity with selectivity toward isoform hCA II, especially, compound 13a with (Ki = 7.6 nM), while the benzoic acid analogues 12d-f, 13b and 15d-f didn't show any activity except compounds 12d,f and 15e that showed weak activity. Additionally, molecular docking was performed for compounds 7a, 8a, 8e, 12a, 13a and 15a on isoform hCA I, II to illustrate the possible interaction with the active site to justify the inhibitory activity.

Palladium-Catalyzed ortho-Benzoylation of Sulfonamides through C?H Activation: Expedient Synthesis of Cyclic N-Sulfonyl Ketimines

The ortho-carbonylation of sulfonylarenes by non-hazardous aryl aldehydes as a carbonyl precursor was reported. In this method, the sulfonamide group serves as a directing group for C?H activation in the presence of a Pd catalyst under ligand-free conditions. The scope of this strategy has been extended to the one-pot two-step synthesis of cyclic N-sulfonyl ketimines under mild reaction conditions. Our approach could be considered as an alternative by circumventing the use of highly reactive organolithium or Grignard reagents to access a wide range of biologically potent cyclic N-sulfonyl ketimines. (Figure presented.).

Tail approach synthesis of novel benzenesulfonamides incorporating 1,3,4-oxadiazole hybrids as potent inhibitor of carbonic anhydrase I, II, IX, and XII isoenzymes

Two new series of 1,3,4-oxadiazole benzenesulfonamide hybrids 3 and 4, having twenty novel compounds, have been designed and synthesized in order to assess their inhibition potential as CAIs against hCA I, II, IX, and XII. ‘Tail approach’ strategy has been used to design the aromatic sulfonamide scaffolds with carbonyl and amide linker. Excellent inhibitory activity against hCA I has been exhibited by compounds 3g and 4j, 3.5 magnitude of order better than reference drug AAZ (KI = 250 nM). Moreover, compound 4j (KI = 7.9 nM) effectively inhibited glaucoma-associated hCA II isoform as well as tumor-associated hCA IX isoform with KI = 16.3 nM. Further hCA XII was weakly inhibited by all the compounds with KI values ranging from 0.23 μM to 3.62 μM. Interestingly structure-activity relationship (SAR) study indicates that N-(3-nitrophenyl)-2-((5-(4-sulfamoylphenyl)-1,3,4-oxadiazol-2-yl)thio)acetamide (4j) is a potent compound to be investigated further for antiglaucoma and antitumor activity. The chemistry of the nature of different substitutions on the 1,3,4-oxadiazole bearing benzenesulfonamide substituted aromatic ring for potency and selectivity over one hCA isoform versus others is deliberated in the present study. In this context, the 1,3,4-oxadiazole motif can be a valuable tool worth developing for the procurement of novel and potent selective CAIs potentially useful for the management of a variety of diseases as chemotherapeutic agents.

Oxadiazole substituted benzenesulfonamide compound and preparation method thereof and application as carbonic anhydrase inhibitor

The invention discloses an oxadiazole substituted benzenesulfonamide compound as shown in a formula I or pharmaceutically acceptable salt thereof, a preparation method of the oxadiazole substituted benzenesulfonamide compound and an application of the oxadiazole substituted benzenesulfonamide compound as a carbonic anhydrase inhibitor. The compound is simple in preparation process, mild in reaction conditions in key steps, higher in yield, lower in energy consumption and more environment-friendly, and the compound shows a good development potential as a carbonic anhydrase inhibitor.

4,6-Substituted-1H-Indazoles as potent IDO1/TDO dual inhibitors

Indoleamine 2,3-dioxygenase 1 (IDO1) and tryptophan 2,3-dioxygenase (TDO) are constitutively overexpressed in many types of cancer cells and exert important immunosuppressive functions. In this article, a series of 4,6-substituted-1H-indazole derivatives were synthesized and evaluated the inhibitory activities against IDO1 and TDO, as well as their structure-activity relationships (SARs). Among these, compound 35 displayed the most IDO1 inhibitory potency with an IC50 value of 0.74 μM in an enzymatic assay and 1.37 μM in HeLa cells. Quantitative analysis of the Western blot results indicated that 35 significantly decreased the INFγ-induced IDO1 expression in a concentration-dependent manner. In addition, 35 showed promising TDO inhibition with an IC50 value of 2.93 μM in the enzymatic assay and 7.54 μM in A172 cells. Moreover, compound 35 exhibited in vivo antitumor activity in the CT26 xenograft model. These findings suggest that 1H-indazole derivative 35 is a potent IDO1/TDO dual inhibitor, and has the potential to be developed for IDO1/TDO-related cancer treatment.

Synthesis and comparative carbonic anhydrase inhibition of new Schiff's bases incorporating benzenesulfonamide, methanesulfonamide, and methylsulfonylbenzene scaffolds

Herein, we report the synthesis, characterization, and carbonic anhydrase (CA) inhibition of the newly synthesized Schiff's bases 4–18 with benzenesulfonamide, methanesulfonamide, and methylsulfonylbenzene scaffolds. The compound inhibition profiles against human CA (hCA) isoforms I, II, IX, and XII were compared to those of the standard inhibitors, acetazolamide (AAZ) and SLC-0111 (a CA inhibitor in Phase II clinical trials for the treatment of hypoxic tumors). The hCA I was inhibited by compounds 4a–8a with inhibition constants (KI) in the range 93.5–428.1 nM (AAZ and SLC-0111: KI, 250.0 and 5080.0 nM, respectively). Compounds 4a–8a proved to be effective hCA II inhibitors, with KI ranging from 18.2 to 133.3 nM (AAZ and SLC-0111: KI, 12.0 and 960.0 nM, respectively). Compounds 4a–8a effectively inhibited hCA IX, with KI in the range 8.5–24.9 nM; these values are superior or equivalent to that of AAZ and SLC-0111 (KI, 25.0 and 45.0 nM, respectively). Compounds 4a–8a displayed effective hCA XII inhibitory activity with KI values ranging from 8.6 to 43.2 nM (AAZ and SLC-0111: KI, 5.7 and 4.5 nM, respectively). However, compounds 9b–13b and 14c–18c were found to be micromolar CA inhibitors. For molecular docking studies, compounds 5a, 6a, and 8a were selected.

Discovery of potent anti-convulsant carbonic anhydrase inhibitors: Design, synthesis, in vitro and in vivo appraisal

We report the design, synthesis and pharmacological assessment of novel benzenesulfonamide derivatives acting as effective carbonic anhydrase (CA, EC 4.2.1.1) inhibitors. All the synthesized compounds were screened for their CA inhibitory action against four isoforms of human origin (h), i.e. hCA I, hCA II, hCA VII and hCA IX. In-vitro carbonic anhydrase inhibition studies have shown that first series, 4-(2-(4-(4-substitutedpiperazin-1-yl)benzylidene)hydrazinyl)benzenesulfonamides (4a- 4i) bestowed low nanomolar range to medium nanomolar range inhibitors against hCA II and hCA VII, effectively involved in epileptogenesis. Furthermore, compounds belonging to the second series, 4-(2-(4-(4-substitutedpiperazin-yl)benzylidene)hydrazinecarbonyl)benzenesulfonamides (8a-8k) showed effective inhibition against hCA VII, being less effective against other hCA isoforms. Inspiring with obtained CA inhibition results, we have chosen some of the potent hCA II and hCA VII inhibitors (4g, 4i and 8d) to test their anti-convulsant efficacy in MES and sc-PTZ seizure tests in Swiss Albino male mice. In result, these compounds significantly attenuated both electrical (MES) as well as chemical (sc-PTZ) induced seizures. Next, in advance anticonvulsant tests, compound 8d displayed long duration of action in time course study and successfully attenuated MES induced seizure in mice up to 6 h after drug administration without showing neurotoxicity in rotarod test. Moreover, this compound was also found to be orally active and effectively abolished generalized tonic-clonic seizures in male Wistar rats upon oral administration, being non-toxic in sub acute toxicity studies.

Novel hydrazido benzenesulfonamides-isatin conjugates: Synthesis, carbonic anhydrase inhibitory activity and molecular modeling studies

As a part of our ongoing efforts towards developing novel carbonic anhydrase inhibitors based on the isatin moiety, herein we report the synthesis and biological evaluation of novel sulfonamides (5a-h, 10a-g and 11a-c) incorporating substituted 2-indolinone moiety (as tail) linked to benzenesulfonamide (as zinc anchoring moiety) through a hydrazide linker. The synthesized sulfonamides were evaluated in vitro for their inhibitory activity against the following human (h) carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, hCA I, II, IX and XII. All these isoforms were inhibited by the sulfonamides reported here in variable degrees. hCA I was inhibited with KIs in the range of 671.8: 3549.5 nM, hCA II in the range of 36.8: 892.4 nM; hCA IX in the range of 8.9: 264.5 nM, whereas hCA XII in the range of 9.0: 78.1 nM. In particular, compound 10b emerged as a single-digit nanomolar hCA IX and XII inhibitor (8.9 and 9.2 nM, respectively). Molecular docking studies carried out for compound 10b within the hCA II, IX and XII active sites allowed us to rationalize the obtained inhibition results.

N-Acylbenzenesulfonamide Dihydro-1,3,4-oxadiazole Hybrids: Seeking Selectivity toward Carbonic Anhydrase Isoforms

A series of N-acylbenzenesulfonamide dihydro-1,3,4-oxadiazole hybrids (EMAC8000a-m) was designed and synthesized with the aim to target tumor associated carbonic anhydrase (hCA) isoforms IX and XII. Most of the compounds were selective inhibitors of the tumor associated hCA XII. Moreover, resolution of EMAC8000d racemic mixture led to the isolation of the levorotatory eutomer exhibiting an increase of hCA XII inhibition potency and selectivity with respect to hCA II. Computational studies corroborated these data. Overall our data indicate that both substitution pattern and stereochemistry of dihydro-1,3,4-oxadiazole could be considered as key factors to determine activity and selectivity toward hCA isozymes. These results can provide further indication for the design and optimization of selective hCA inhibitors.

SULFONYLAMINOCARBONYL DERIVATIVE, PHARMACEUTICAL COMPOSITION AND USES THEREOF

This disclosure is related to a sulfonylaminocarbonyl derivative of formula (I) and/or a pharmaceutically acceptable salt thereof, a pharmaceutical composition comprising the sulfonylaminocarbonyl derivatives of formula (I) and/or a pharmaceutically acceptable salt thereof, preparation methods thereof, and use thereof in treating FXR and/or TGR5 mediated diseases, including primary biliary cirrhosis, nonalcoholic fatty liver, portal hypertension, bile acid diarrhea and cholestasis, type II diabetes and obesity, etc.