5317-94-2

Usage

InChI:InChI=1/C15H15NO3S/c1-11-3-9-15(10-4-11)20(18,19)16-14-7-5-13(6-8-14)12(2)17/h3-10,16H,1-2H3

Upstream product

• 99-92-3 p-aminobenzophenone 
• 98-59-9 p-toluenesulfonyl chloride 
• 99-90-1 para-bromoacetophenone 
• 70-55-3 toluene-4-sulfonamide 
• 98-09-9 benzenesulfonyl chloride 
• 31125-05-0 1-(4-nitrosophenyl)ethan-1-one 
• 106-49-0 p-toluidine 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 100-19-6 (4-nitrophenyl)ethanone 

Downstream Products

• 72178-39-3 N-(4-cinnamoylphenyl)-4-methylbenzenesulfonamide 
• 17687-47-7 mono-N-methylaminoacetophenone 
• 72178-39-3 (E)-N-(4-cinnamoylphenyl)-4-methylbenzenesulfonamide 
• 1253375-17-5 N-(4-acetylphenyl)-4-methyl-N-vinylbenzenesulfonamide 
• 951658-85-8 N-(4-(3-(4-hydroxyphenyl)acryloyl)phenyl)-4-methylbenzenesulfonamide 
• 951658-84-7 4'-(4-toluenesulfonamide)-3,4-dihydroxychalcone 
• 1032476-48-4 4'-(4-toluenesulfonamide)-2,4-dihydroxychalcone 
• 1032476-49-5 4'-(4-toluenesulfonamide)-2,5-dihydroxychalcone 
• 1430223-95-2 N-(4-(5-cyano-4-(4-isopropylphenyl)-6-oxo-1,6-dihydropyridin-2-yl)pheny)-4-methylbenzensulfonamide 
• 1430223-96-3 N-(4-(5-cyano-6-oxo-4-(4-thien-2-yl)-1,6-dihydropyridin-2-yl)phenyl)-4-methylbenzensulfonamide 
• 1430224-01-3 N-(4-(5-cyano-4-(isopropylphenyl)-6-(β-D-glucopyranosyloxy)-1,6-dihydropyridin-2-yl)phenyl)-4-methylbenzenesulfonamide 
• 1430224-02-4 N-(4-(5-cyano-6-(β-D-glucopyranosyloxy)-4-(thien-2-yl)-1,6-dihydropyridin-2-yl)phenyl)-4-methylbenzenesulfonamide 
• 1430224-03-5 N-(4-(5-cyano-4-(isopropylphenyl)-6-oxo-1-(β-D-glucopyranosyl)-1,6-dihydropyridin-2-yl)phenyl)-4-methylbenzenesulfonamide 
• 1430224-04-6 N-(4-(5-cyano-6-oxo-4-(thien-2-yl)-1-(β-D-glucopyranosyl)-1,6-dihydropyridin-2-yl)phenyl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Design, synthesis and molecular modeling study of certain 4-Methylbenzenesulfonamides with CDK2 inhibitory activity as anticancer and radio-sensitizing agents

Two series of 2-aminopyridine derivatives 6-17 and tyrphostin AG17 analogs 18-22 bearing 4-methylbenzenesulfonamide moiety were designed and synthesized as anticancer compounds. The synthesized compounds were biologically evaluated for their cytotoxic act

Synthesis of new pyridines with sulfonamide moiety: via a cooperative vinylogous anomeric-based oxidation mechanism in the presence of a novel quinoline-based dendrimer-like ionic liquid

In the present study, we reported the synthesis of a novel quinoline-based dendrimer-like ionic liquid. After characterization of the mentioned ionic liquid with suitable techniques such as Fourier transform infrared spectroscopy (FT-IR), energy dispersive X-ray spectroscopy (EDX), elemental mapping, thermogravimetric analysis (TGA) and derivative thermogravimetry (DTG), its catalytic performance was investigated in the synthesis of new pyridines with sulfonamide moiety via a cooperative vinylogous anomeric-based oxidation mechanism under mild reaction conditions. All target molecules were achieved in short reaction times and high yields. This journal is

Discovery of pyridine- sulfonamide hybrids as a new scaffold for the development of potential VEGFR-2 inhibitors and apoptosis inducers

New sulfonamide derivatives have been synthesized and tested as antitumor agents. All newly synthesized compounds were tested in vitro against 60 lines of human cancer cells. Compound VIIb shows broad-spectrum activity with a mean inhibition value of 91.67% against all cell lines. It exhibited potent anticancer activity with GI50 values of 1.06–8.92 μM relative to most of the tested cancer cell lines. Compound VIIb has been tested for enzyme inhibition activity toward vascular endothelial growth factor receptor 2, where VEGFR-2 was potently inhibited at a lower IC50 value of 3.6 μM, compared with sorafenib (IC50 = 4.8 μM). Hybrid VIIb was also able to induce cell cycle disturbance and apoptosis in Renal UO-31 cells, as shown by DNA flow cytometry and Annexin V-FITC/PI assays. It has also revealed lower Bcl-2 protein expression anti-apoptotic levels and higher BAX, p53, and caspases 3 expression levels.

Synthesis, biological evaluation and molecular docking of new sulfonamide-based indolinone derivatives as multitargeted kinase inhibitors against leukemia

Series of novel sulfonamide-based 3-indolinones 3a-m and 4a-f were designed, synthesized and then their cytotoxic activity was evaluated against a panel of sixty cancer cell lines. This screening indicated that 4-(2-(5-fluoro-2-oxoindolin-3-ylidene)acetyl)phenyl benzenesulfonate (4f) possessed promising cytotoxicity against CCRF-CEM and SR leukemia cell lines with IC50 values 6.84 and 2.97 μM, respectively. Further investigation of the leukemic cytotoxicity of compound 4f was carried out by performing PDGFRα, VEGFR2, Aurora A/B and FLT3 enzyme assays and CCRF-CEM and SR cell cycle analysis. These investigations showed that compound 4f exhibited pronounced dual inhibition of both kinases PDGFRα and Aurora A with potency of 24.15 and 11.83 nM, respectively. The in vitro results were supported by molecular docking studies in order to explore its binding affinity and its key amino acids interactions. This work represents compound 4f as a promising anticancer agent against leukemia.

Nitrosoarenes as Nitrogen Source for Generation of Sulfonamides with the Insertion of Sulfur Dioxide under Metal-Free Conditions?

A metal-free reaction of nitrosoarenes, aryldiazonium tetrafluoroborates, and sulfur dioxide under mild conditions is developed, giving rise to sulfonamides in moderate to good yields. This transformation proceeds efficiently at room temperature in the presence of cyclohexa-1,4-diene with a broad reaction scope. Good functional group compatibility is observed, including cyano, halo, and ester. A plausible mechanism involving a radical process with the insertion of sulfur dioxide is proposed, and cyclohexa-1,4-diene serves as the reductant during the transformation.

Copper-catalyzed redox coupling of nitroarenes with sodium sulfinates

A simple copper-catalyzed redox coupling of sodium sulfinates and nitroarenes is described. In this process, abundant and stable nitroarenes serve as both the nitrogen sources and oxidants, and sodium sulfinates act as both reactants and reductants. A variety of aromatic sulfonamides were obtained in moderate to good yields with broad substrate scope. No external additive is employed for this kind of transformation.

Copper-catalysed hydroamination of N-allenylsulfonamides: The key role of ancillary coordinating groups

A copper-catalysed hydroamination reaction of N-allenylsulfonamides with amines has been developed through a rational approach based on mechanistic studies. The reaction is promoted by a simple copper(I) catalyst and proceeds at room temperature with complete regioselectivity and excellent stereoselectivity towards linear (E)-N-(3-aminoprop-1-enyl)sulfonamides. Density Functional Theory (DFT) studies allow interpreting the key role of unsaturated substituents on nitrogen as ancillary coordinating moieties for the copper catalyst.

Triple Mode of Alkylation with Ethyl Bromodifluoroacetate: N, or O-Difluoromethylation, N-Ethylation and S-(ethoxycarbonyl)difluoromethylation

In this report, we have explored a triple mode of chemical reactivity of ethyl bromodifluoroacetate. Typically, bromodifluoroacetic acid has been used as a difluorocarbene precursor for difluoromethylation of soft nucleophiles. Here we have disclosed nucleophilicity and base dependent divergent chemical reactivity of ethyl bromodifluoroacetate. It furnishes lithium hydroxide and cesium carbonate promoted difluoromethylation of tosyl-protected aniline and electron-deficient phenols respectively. Interestingly, switching the base from lithium hydroxide to 4-N,N-dimethylamino pyridine (DMAP) tosyl-protected anilines afforded the corresponding N-ethylation product. Whereas, highly nucleophilic thiophenols furnished the corresponding S-carboethoxydifluoromethylation product via a rapid SN2 attack to the bromine atom prior to the ester hydrolysis. This mechanistic divergence was established through several control experiments. It was revealed that difluoromethylation reaction proceeds through a tandem in situ ester hydrolysis/decarboxylative-debrominative difluorocarbene formation and subsequent trapping by the soft nucleophile-NHTs or electron-deficient phenolic ?OH groups. In the presence of DMAP the hydrolysis of the ester is perturbed instead a nucleophilic attack at the ethyl moiety provides the N-ethylation product. Hence, besides the development of a practical base-promoted N-difluoromethylation of amines and electron-deficient phenols, divergent reactivity pattern of inexpensive and user-friendly ethyl bromodifluoroacetate has been explored. (Figure presented.).

Purine-ring-containing benzene sulfonamide chalcone derivative and preparation and application methods thereof

The invention discloses a purine-ring-containing benzene sulfonamide chalcone derivative and preparation and application methods thereof. The purine-ring-containing benzene sulfonamide chalcone derivative has a formula (I) shown as below, in which R1 is 4-oxymethyl, 4-tert-butyl, 4-methyl, 4-flouride, 4-bromide, 2-methyl, 2-fluoride, 2-chloride, 2-bromide and hydrogen atom and R2 is methyl, ethyland benzyl. The purine-ring-containing benzene sulfonamide chalcone derivative can inhibit tobacco mosaic virus, cucumber mosaic virus, potato Y virus and southern rice black-streaked dwarf virus.

Discovery and structure-activity relationship of novel 4-hydroxy-thiazolidine-2-thione derivatives as tumor cell specific pyruvate kinase M2 activators

Pyruvate kinase M2 isoform (PKM2) is a crucial protein responsible for aerobic glycolysis of cancer cells. Activation of PKM2 may alter aberrant metabolism in cancer cells. In this study, we discovered a 4-hydroxy-thiazolidine-2-thione compound 2 as a novel PKM2 activator from a random screening of an in-house compound library. Then a series of novel 4-hydroxy-thiazolidine-2-thione derivatives were designed and synthesized for screening as potent PKM2 activators. Among these, some compounds showed higher PKM2 activation activity than lead compound 2 and also exhibited significant anti-proliferative activities on human cancer cell lines at nanomolar concentration. The compound 5w was identified as the most potent antitumor agent, which showed excellent anti-proliferative effects with IC50 values from 0.46 μM to 0.81 μM against H1299, HCT116, Hela and PC3 cell lines. 5w also showed less cytotoxicity in non-tumor cell line HELF compared with cancer cells. In addition, Preliminary pharmacological studies revealed that 5w arrests the cell cycle at the G2/M phase in HCT116 cell line. The best PKM2 activation by compound 5t was rationalized through docking studies.