13269-73-3

Usage

Uses

Used in Pharmaceutical Industry:
3-METHYL-1-(4'-SULFOAMIDOPHENYL)-5-PYRA& is used as a potential candidate in drug discovery and development for its potential pharmaceutical applications. Its unique structure and properties make it a subject of interest for researchers looking to innovate and develop new therapeutic agents.
Given the provided materials, there are no specific applications detailed for 3-METHYL-1-(4'-SULFOAMIDOPHENYL)-5-PYRA&. However, its mention as a compound with potential pharmaceutical applications suggests that it could be utilized in various therapeutic areas once its specific activities and properties are further explored and understood.

InChI:InChI=1/C10H11N3O3S/c1-7-6-10(14)13(12-7)8-2-4-9(5-3-8)17(11,15)16/h2-5H,6H2,1H3,(H2,11,15,16)

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 4392-54-5 4-aminosulfonylphenylhydrazine 
• 141-97-9 ethyl acetoacetate 
• 17852-52-7 4-hydrazinobenzene-1-sulfonamide hydrochloride 
• 63-74-1 sulfanilamide 
• 5977-14-0 acetoacetamido 

Downstream Products

• 441782-66-7 C₂₃H₂₀N₄O₆S 
• 95348-30-4 4-(2,3-dimethyl-5-oxo-2,5-dihydro-1H-pyrazol-1-yl)benzenesulfonamide 
• 1498334-98-7 4-(4-((dimethylamino)methyl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonamide 
• 1498335-10-6 N'-(4-(4-((dimethylamino)methylene)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)phenylsulfonyl)-N,N-dimethylformimidamide 
• 1498335-02-6 4-(4-(cyanomethyl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl) benzenesulfonamide 
• 1498335-05-9 2-(3-methyl-5-oxo-1-(4-sulfamoylphenyl)-4,5-dihydro-1H-pyrazol-4-yl)acetic acid 
• 1498335-08-2 methyl 2-(3-methyl-5-oxo-1-(4-sulfamoylphenyl)-4,5-dihydro-1H-pyrazol-4-yl)acetate 
• 1498335-13-9 4-(4-(hydroxymethylene)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonamide 

Relevant academic research and scientific papers

Arylidene analogues as selective COX-2 inhibitors: synthesis, characterization, in silico and in?vitro studies

Pyrazole derivatives are known to be as non-steroidal anti-inflammatory drugs (NSAID). Celecoxib is the pioneer sulfonamide being pyrazole derivative COX-2 inhibitors, which used to treat pain and inflammation; they may also have a role in cancer prevention. In the present investigation, a series of arylidene analogues (NDP-4011 to NDP-4016) were synthesized by the condensation of 4-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl) benzenesulfonamide (I) with various substituted aromatic aldehydes in ethanol using a catalytic amount of piperidine. All the synthesized compounds were well characterized by IR, 1H NMR, 13C NMR and mass spectrometry. The cytotoxicity of synthesized compounds was tested on the NRK-52E cell line. From which NDP-4011, NDP-4012, NDP-4013, NDP-1015 and NDP-4016 were found to have higher cytotoxicity whereas NDP-4014 showed less cytotoxicity compared to Celecoxib. The in silico pharmacokinetic parameters of compounds were evaluated to check their candidature as a drug. Molecular docking was carried out on COX-2 structures, which revealed that NDP-4011 to NDP-4016 targets allosteric binding site similar to the binding mode of the selective COX inhibitor Celecoxib. Furthermore, results of in?vitro COX-2 inhibition assay supports arylidene analogues as COX-2 inhibitors.

Anticancer effects of new dibenzenesulfonamides by inducing apoptosis and autophagy pathways and their carbonic anhydrase inhibitory effects on hCA I, hCA II, hCA IX, hCA XII isoenzymes

In this study, new dibenzensulfonamides, 7–9, having the chemical structure 4,4′-(5′-chloro-3′-methyl-5-aryl-3,4-dihydro-1′H,H-[3,4′-bipyrazole]-1′,2-diyl)dibenzenesulfonamide were synthesized in five steps to develop new anticancer drug candidates. Their chemical structures were confirmed by 1H NMR, 13C NMR and HRMS spectra. Cytotoxicities of the dibenzensulfonamides were investigated towards HCC1937, MCF7, HeLa, A549 as tumor cell lines and towards MRC5 and Vero as non-tumor cells. Carbonic anhydrase (CAs, EC 4.2.1.1) inhibitory effects of the dibenzensulfonamides 7–9 were also evaluated on the cytosolic human (h) hCA I and II and the tumor-associated hCA IX and XII isoenzymes. Results indicate that both 7 and 8 induced cleavage of poly (ADP ribose) polymerase (PARP), activation of caspases -3, -7 and -9 which are the hallmarks of apoptosis. Meanwhile both compounds induced autophagy in HCC1937 cells which is shown by enhanced expression of LC3 and decreased level of p62 protein. The compounds tested were also effectively inhibited tumor-associated hCA IX and hCA XII isoenzymes in the range of 20.7–28.1 nM and 4.5–9.3 nM, respectively.

Sulfonamide bearing pyrazolylpyrazolines as potent inhibitors of carbonic anhydrase isoforms I, II, IX and XII

Abstract A series of pyrazolylpyrazolines was designed, synthesized and evaluated for carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity against cytosolic human (h) isozymes hCA I and hCA II as well as transmembrane tumor associated isozymes, hCA IX and hCA XII. All the tested compounds exhibited an excellent CA activity profile against hCA I, hCA II and hCA XII when compared to the reference drug acetazolamide (AZA). Compounds 6d, 6f and 7a-7f have exhibited better inhibition profile against hCA XII (Ki = 0.47-5.1 nM) as compared with AZA (Ki = 5.7 nM) especially, compounds 6a, 7a, 7c and 7d which were nearly 10-fold better than reference drug. Against hCA II, all of the tested compounds were better than the standard drug especially compounds 6c, 6d, 7c and 7d (Ki = 1.1-1.7 nM) were many fold better inhibitors than AZA (Ki = 12.1 nM). In addition, they acted as selective CA inhibitors of isoform hCA XII over the physiological isoform hCA I.

Synthesis and anti-inflammatory activity of some new thiadiazole linked pyrazole benzene sulphonamides as cyclooxygenase inhibitors

A new series of thiadiazole linked pyrazole benzenesulfonamide derivatives were synthesized by the condensation of aldehydic pyrazole with aryl substituted thiadiazole amine followed by Schiff base reaction. The synthesized compounds (6a-o) were characterized by IR, NMR, and Mass spectral data, further evaluated their in-vivo anti-inflammatory, analgesic and invitro COX-II inhibition assay. The compounds 6b and 6m showed most significant in-vivo antiinflammatory with 72.33 &71.17% inhibition along analgesic activity having 67.89% and 71.37 % respectively. Their selectivity against COX-II enzyme with selectivity index 67.81 and 66.38 was established for 6b and 6m, which is compared with Celecoxib. During the gastric ulceration study, selected compounds couldn't observed any ulcerogenic effect on gastric mucosa. The in-silico pharmacokinetic profile and molecular docking study exposed very good binding affinity towards the Cyclooxygenase (COX-II) enzyme (PDB Id: 3PGH), therefore the compounds 6b and 6m are used as promising lead candidates for the support of drug development.

Pyrazolone derivatives: Synthesis, anti-inflammatory, analgesic quantitative structure-activity relationship and in vitro studies

Some 1-(4-chlorophenyl or benzenesulfonamide)-2,3- and/or 4-substituted-1H-pyrazol-5(4H)-one derivatives were synthesized and screened for their anti-inflammatory and analgesic activities, in addition to their ulcerogenic liability. They were found to be active as anti-inflammatory and analgesic agents. Compound 6b was found to be the most active as anti-inflammatory agent and compound 9b was found to be the most active one as anti-inflammatory and analgesic agent. On the other hand, cyclooxygenase-1/-2 (COX-1)/COX-2 isozyme selectivity was also done and the tested compounds showed equal inhibition to both isoforms. Moreover, 2D-quantitative structure-activity relationship (QSAR) studies revealed well predictive and statistically significant and cross validated QSAR model that helps to explore some expectedly potent compounds.

Virtual ligand screening of the p300/CBP histone acetyltransferase: Identification of a selective small molecule inhibitor

The histone acetyltransferase (HAT) p300/CBP is a transcriptional coactivator implicated in many gene regulatory pathways and protein acetylation events. Although p300 inhibitors have been reported, a potent, selective, and readily available active-sitedirected small molecule inhibitor is not yet known. Here we use a structure-based, in silico screening approach to identify a commercially available pyrazolone- containing small molecule p300 HAT inhibitor, C646. C646 is a competitive p300 inhibitor with a Ki of 400 nM and is selective versus other acetyltransferases. Studies on site-directed p300 HAT mutants and synthetic modifications of C646 confirm the importance of predicted interactions in conferring potency. Inhibition of histone acetylation and cell growth by C646 in cells validate its utility as a pharmacologic probe and suggest that p300/CBP HAT is a worthy anticancer target.

Thrombopoietin mimetics

Non-peptide TPO mimetics are disclosed, as well as a method of treating thrombocytopenia, in a mammal, including a human, in need thereof, which comprises administering to such mammal an effective amount of a selected hydroxy-1-azo-naphthalene derivative.

Synthesis of 3-Methyl-1-Phenyl-5-Pyrazolones Containing Arylaminosulfonyl Groups

N-Aryl-substituted 3(4)-aminobenzenesulfonamides were synthesized.They are the starting compounds for the production of the corresponding substituted 3(4)-(3-methyl-5-oxo-2-pyrazolin-1-yl)-N-phenylbenzenesulfonamides.Data from the IR, PMR, and mass spectra are presented, and the fragmentation of the molecules is discussed.