6933-51-3

Usage

Uses

Used in Organic Synthesis:
N-(2-nitrophenyl)benzenesulfonamide is used as an intermediate or reagent in organic synthesis for its ability to facilitate the creation of various organic compounds.
Used in Pharmaceutical Industry:
N-(2-nitrophenyl)benzenesulfonamide is used as a precursor in the production of pharmaceuticals due to its chemical properties that can be harnessed to develop new drugs.
Used in Dye Production:
In the dye industry, N-(2-nitrophenyl)benzenesulfonamide is used as a component in the synthesis of dyes, leveraging its color-producing characteristics.
Used in Medicinal Applications:
N-(2-nitrophenyl)benzenesulfonamide is used as a potential candidate in medicinal applications because of its anti-bacterial and anti-fungal properties, which can be utilized to develop treatments for various infections.
Used in Light-curable Materials Production:
N-(2-nitrophenyl)benzenesulfonamide is used as a photoinitiator in the production of light-curable materials, taking advantage of its ability to initiate polymerization reactions upon exposure to light.

InChI:InChI=1/C12H10N2O4S/c15-14(16)12-9-5-4-8-11(12)13-19(17,18)10-6-2-1-3-7-10/h1-9,13H

Upstream product

• 1678-25-7 N-phenylbenzenesulfonamide 
• 88-74-4 2-nitro-aniline 
• 98-09-9 benzenesulfonyl chloride 
• 938-10-3 phenylsulfonyl azide 
• 577-19-5 2-nitrophenyl bromide 
• 98-10-2 benzenesulfonamide 
• 93-98-1 N-phenyl benzoyl amide 
• 89-63-4 4-Chloro-2-nitroaniline 
• 1493-27-2 ortho-nitrofluorobenzene 

Downstream Products

• 43200-31-3 N-(2-amino-4-chlorophenyl)benzenesulfonamide 
• 4106-18-7 1-(phenylsulfonyl)-1H-benzo[d][1,2,3]triazole 
• 176649-73-3 N-<2-(2,3-Dihydroxypropyl)cyclohex-2-enyl>-N-(2-nitrophenyl)benzenesulfonamide 
• 176649-76-6 N-(2-Nitrophenyl)-N-<2-(2-oxoethyl)cyclohex-2-enyl>benzenesulfonamide 
• 176649-79-9 N-<2-(2-Hydroxyethyl)cyclohex-2-enyl>N-(2-nitrophenyl)benzenesulfonamide 
• 176649-82-4 N-2-(Aminophenyl)-N-<2-(2-hydroxyethyl)cyclohex-2-enyl>benzenesulfonamide 
• 209685-43-8 methyl 4-[({5-chloro-2-[(phenylsulfonyl)amino]phenyl}amino)carbonyl]benzoate 
• 176649-70-0 N-(2-Nitrophenyl)-N-(2-prop-2-enylcyclohex-2-enyl)benzenesulfonamide 
• 21226-39-1 benzenesulfonic acid-(N-methyl-2-nitro-anilide) 
• 107620-50-8 benzenesulfonic acid-[N-(2-hydroxy-ethyl)-2-nitro-anilide] 

Relevant academic research and scientific papers

Synthesis of Structurally Diverse Benzotriazoles via Rapid Diazotization and Intramolecular Cyclization of 1,2-Aryldiamines

An operationally simple method has been developed for the preparation of N-unsubstituted benzotriazoles by diazotization and intramolecular cyclization of a wide range of 1,2-aryldiamines under mild conditions, using a polymer-supported nitrite reagent and p-tosic acid. The functional group tolerance of this approach was further demonstrated with effective activation and cyclization of N-alkyl, -aryl, and -acyl ortho-aminoanilines leading to the synthesis of N1-substituted benzotriazoles. The synthetic utility of this one-pot heterocyclization process was exemplified with the preparation of a number of biologically and medicinally important benzotriazole scaffolds, including an α-amino acid analogue.

METHODS OF INHIBITING BACTERIAL VIRULENCE AND COMPOUNDS RELATING THERETO

The present invention relates to compounds and methods for the treatment of bacterial infections. Because their mechanism of action does not involve killing of bacteria or inhibiting their growth, the potential for these compounds to induce drug resistance in bacteria is minimized. Through inhibiting bacterial virulence, the present invention provides a novel means of treating bacterial infections.

Palladium nanoparticles as reusable catalyst for the synthesis of N-aryl sulfonamides under mild reaction conditions

An efficient palladium nanoparticles-catalyzed N-arylation of sulfonamides and sulfonyl azides is described. This procedure serves as an active protocol for intermolecular C-N bond formation using Pd(OAc)2 in PEG-400 under air. Aryl bromides and triflates react at 35°C, while aryl chlorides require heating to 50°C and give the desired products only in low yields. This reaction proceeds smoothly in acceptable yields using low catalyst loading.

Nanocopper-mediated direct arylsulfonamidation of aryl halides with arylsulfonyl azides

An efficient protocol for direct arylsulfonamidation of aryl iodides and aryl bromides using arylsulfonylazides catalyzed by copper nanoparticles is described. Iranian Chemical Society 2012.

Potent anti-prostate cancer agents derived from a novel androgen receptor down-regulating agent

The search for novel androgen receptor (AR) down-regulating agents by catalyst HipHop pharmacophore modeling led to the discovery of some lead molecules. Unexpectedly, the effect of these leads on human prostate cancer LNCaP cell viability did not correlate with the ability of the compounds to cause down-regulation of AR protein expression. Through rational synthetic optimization of the lead compound (BTB01434), we have discovered a series of novel substituted diaryl molecules as potent anti-prostate cancer agents. Some compounds (1-6) were shown to be extremely potent inhibitors of LNCaP cell viability with GI50 values in the nanomolar range (1.45-83 nM). The most potent compound (4-methylphenyl)[(4-methylphenyl)sulfonyl]amine (5) with a GI50 value of 1.45 nM is 27,000 times more potent than our lead compound BTB01434 (GI50 = 39.8 μM). In addition, some of the compounds exhibited modest anti-androgenic activities and one was also a potent inhibitor (GI50 = 850 nM) of PC-3 (AR-null) cell growth. A clear structure-activity relationship (SAR) has been established for activity against LNCaP cells, where potent molecules possess two substituted/unsubstituted aromatic rings connected through a sulfonamide linker. These novel compounds are strong candidates for development for the treatment of hormone-sensitive and importantly hormone-refractory prostate cancers in humans.

ANTI-CANCER AGENTS AND ANDROGEN INHIBITION ACTIVITY COMPOUND

A qualitative 3D pharmacophore model (a common feature based model or Catalyst HipHop algorithm) developed from well-known natural product androgen receptor down-regulating agents (ARDAs). The 3D pharmacophore model is used as a template in virtual screening compounds for new ARDAs. ARDA compounds and compounds that strongly inhibit the growth of human prostate LNCaP cells. The compounds may be used in compositions and methods of inhibiting cell proliferation of a cancer and methods of preventing or treating cancer, including prostate cancer.

Discovery of new chemical leads for selective EP1 receptor antagonists

A series of 4-({2-[alkyl(phenylsulfonyl)amino]phenoxy}methyl)benzoic acids were identified as functional PGE2 antagonists with selectivity for the EP1 receptor subtype starting from a chemical lead 1, which was found while screening our in-house compound library. Discovery of the optimized analogs 21-23 is presented here and structure-activity relationships (SAR) are also discussed.

Ortho effect in dissociation of substituted N-phenylbenzenesulfonamides

Twenty-five 2,2′-disubstituted N-phenylbenzenesulfonamides (2-X-C6H4SO2NHC6H4-Y-Z′) were synthesised and their purity checked by elemental analysis. This set of model substrates involved all possible combinations of methoxy, methyl, hydrogen, chloro, and nitro substituents. The dissociation constants of the sulfonamides were determined by potentiometric titration in methanol, pyridine, dimethyl sulfoxide, N,N-dimethylformamide, acetone, and acetonitrile. The dissociation constants pKHA obtained were correlated with various sets of substituent constants describing electronic and steric effects of the substituents, and the statistically treated data were used to discuss the contribution of the substituent effects in the dissociation and the difference between the effects transmitted from the two rings. A linear regression model explaining 99% of the variability of experimental data in all the solvents has been found and discussed. Moreover, the experimental data were also interpreted by the methods using latent variables, the principal component analysis (PCA) and conjugated deviation analysis (CDA), and two latent variables were shown to be statistically significant in the description of dissociation. The first obviously describes common action of electronic and steric effects of substituents; the other probably concerns a combined effect of substituent and solvent on the position of acid-base equilibrium.

Selective monodesulfonylation of N,N-disulfonylarylamines with tetrabutylammonium fluoride

The monodesulfonylation reaction of N,N-bis(methylsulfonyl)-, N,N- bis(phenylsulfonyl)-, and N,N-bis(p-tolylsulfonyl)arylamines easily proceeded using tetrabutylammonium fluoride in tetrahydrofuran under mild conditions to give the corresponding N-monosulfonylarylamines in excellent yields.