16803-92-2

Basic information

• Product Name: 4-AMINO-N-(4-CHLORO-PHENYL)-BENZENESULFONAMIDE
• Synonyms: 4-AMINO-N-(4-CHLORO-PHENYL)-BENZENESULFONAMIDE;AKOS B014350;ART-CHEM-BB B014350;TIMTEC-BB SBB009347;BenzenesulfonaMide,4-aMino-N-(4-chlorophenyl)-
• CAS NO: 16803-92-2
• Molecular Formula: C₁₂H₁₁ClN₂O₂S
• Molecular Weight: 282.75
• Mol File: 16803-92-2.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 468.8 °C at 760 mmHg
• Flash Point: 237.3 °C
• Appearance: /
• Density: 1.466 g/cm³
• Vapor Pressure: 5.79E-09mmHg at 25°C
• Refractive Index: 1.674
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: 4-AMINO-N-(4-CHLORO-PHENYL)-BENZENESULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-N-(4-CHLORO-PHENYL)-BENZENESULFONAMIDE(16803-92-2)
• EPA Substance Registry System: 4-AMINO-N-(4-CHLORO-PHENYL)-BENZENESULFONAMIDE(16803-92-2)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 16803-92-2(Hazardous Substances Data)

Usage

General Description

4-AMINO-N-(4-CHLORO-PHENYL)-BENZENESULFONAMIDE, also known as N-(4-Chlorophenyl)sulfanilamide, is a chemical compound commonly used as an intermediate in the synthesis of pharmaceuticals. It has a molecular formula of C12H11ClN2O2S and a molecular weight of 284.745 g/mol. 4-AMINO-N-(4-CHLORO-PHENYL)-BENZENESULFONAMIDE is typically synthesized through the reaction of 4-aminobenzenesulfonamide with 4-chloronitrobenzene in the presence of a catalyst. It is a crystalline powder that is sparingly soluble in water but soluble in organic solvents. This chemical has been studied for its potential applications in the development of various medications, particularly those targeting diseases and conditions such as cancer and bacterial infections.

InChI:InChI=1/C12H11ClN2O2S/c13-9-1-5-11(6-2-9)15-18(16,17)12-7-3-10(14)4-8-12/h1-8,15H,14H2

Upstream product

• 19837-92-4 N-(4-{[(4-chlorophenyl)amino]sulfonyl}phenyl)acetamide 
• 16937-03-4 N-(4-chlorophenyl)-4-nitrobenzenesulfonamide 
• 106-47-8 4-chloro-aniline 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 103-84-4 Acetanilid 

Downstream Products

• 1160499-45-5 dimethyl (2E,4Z)-4-[({4-[(4-chlorophenyl)sulfamoyl]phenyl}amino)methylene]pent-2-enedioate 
• 22786-85-2 2-chloro-4'-[(p-chlorophenyl)sulfamoyl]-acetanilide 
• 1160212-20-3 C₁₉H₁₅ClN₂O₆S 
• 1258977-92-2 6-hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro[1,7]phenanthroline-3-carboxylic acid [4-(4-chlorophenylsulfamoyl)phenyl]amide 
• 1258977-80-8 6-chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro[1,7]phenanthroline-3-carboxylic acid [4-(4-chlorophenylsulfamoyl)phenyl]amide 

Relevant articles and documents

Comparative study between the anti-P. falciparum activity of triazolopyrimidine, pyrazolopyrimidine and quinoline derivatives and the identification of new PfDHODH inhibitors

In this work, we designed and synthesized 35 new triazolopyrimidine, pyrazolopyrimidine and quinoline derivatives as P. falciparum inhibitors (3D7 strain). Thirty compounds exhibited anti-P. falciparum activity, with IC50 values ranging from 0.030 to 9.1 μM. The [1,2,4]triazolo[1,5-a]pyrimidine derivatives were more potent than the pyrazolo[1,5-a]pyrimidine and quinoline analogues. Compounds 20, 21, 23 and 24 were the most potent inhibitors, with IC50 values in the range of 0.030–0.086 μM and were equipotent to chloroquine. In addition, the compounds were selective, showing no cytotoxic activity against the human hepatoma cell line HepG2. All [1,2,4]triazolo[1,5-a]pyrimidine derivatives inhibited PfDHODH activity in the low micromolar to low nanomolar range (IC50 values of 0.08–1.3 μM) and did not show significant inhibition against the HsDHODH homologue (0–30% at 50 μM). Molecular docking studies indicated the binding mode of [1,2,4]triazolo[1,5-a]pyrimidine derivatives to PfDHODH, and the highest interaction affinities for the PfDHODH enzyme were in agreement with the in vitro experimental evaluation. Thus, the most active compounds against P. falciparum parasites 20 (R = CF3, R1 = F; IC50 = 0.086 μM), 21 (R = CF3; R1 = CH3; IC50 = 0.032 μM), 23, (R = CF3, R1 = CF3; IC50 = 0.030 μM) and 24 (R = CF3, 2-naphthyl; IC50 = 0.050 μM) and the most active inhibitor against PfDHODH 19 (R = CF3, R1 = Cl; IC50 = 0.08 μM - PfDHODH) stood out as new lead compounds for antimalarial drug discovery. Their potent in vitro activity against P. falciparum and the selective inhibition of the PfDHODH enzyme strongly suggest that this is the mechanism of action underlying this series of new [1,2,4]triazolo[1,5-a]pyrimidine derivatives.

Synthesis, characterization, crystal structures and biological screening of 4-amino quinazoline sulfonamide derivatives

Three quinazolin-4-ylamino derivatives containing phenylbenzenesulfonamides (7a-7c)were synthesized by reacting (E)-N'-(2-cyanophenyl)-N,N-dimethyl formamidine (6)with different 4-amino-N-(phenyl)benzenesulfonamides (4a-4c)and characterized by different techniques such as HRMS, IR, 1H NMR and 13C NMR spectroscopy. The structural properties were further examined by single crystal X-ray diffraction method. The X-ray data shows that compounds 7a and 7c contain two molecules and 7b contains one molecule in the asymmetric unit. Comparison of conformation of two distinct molecules, “A” and “B”, in the asymmetric unit of 7a and 7c were studied with the aid of reported literature. The in vitro antiproliferative activity of the compounds was tested against two breast cancer cell lines (MDA-MB-231 and MCF7). Compound 7b observed as a highest potent candidate against MDA-MB-231with IC50 of 5.44 μg/mL. Antimicrobial activity was also screened against bacterial and fungal strains. Compound 7a with chloro substitution was observed as the most potent candidate against the Gram-negative bacterial strains, whereas the compounds showed no significant activity against the fungal strain.

Synthesis, molecular structure, anticancer activity, and QSAR study of N-(Aryl/heteroaryl)-4-(1h-pyrrol-1-yl)benzenesulfonamide derivatives

A series of N-(aryl/heteroaryl)-4-(1H-pyrrol-1-yl)benzenesulfonamides were synthesized from 4-amino-N-(aryl/heteroaryl)benzenesulfonamides and 2,5-dimethoxytetrahydrofuran. All the synthesized compounds were evaluated for their anticancer activity on HeLa, HCT-116, and MCF-7 human tumor cell lines. Compound 28, bearing 8-quinolinyl moiety, exhibited the most potent anticancer activity against the HCT-116, MCF-7, and HeLa cell lines, with IC50 values of 3, 5, and 7 μM, respectively. The apoptotic potential of the most active compound (28) was analyzed through various assays: phosphatidylserine translocation, cell cycle distribution, and caspase activation. Compound 28 promoted cell cycle arrest in G2/M phase in cancer cells, induced caspase activity, and increased the population of apoptotic cells. Relationships between structure and biological activity were determined by the QSAR (quantitative structure activity relationships) method. Analysis of quantitative structure activity relationships allowed us to generate OPLS (Orthogonal Projections to Latent Structure) models with verified predictive ability that point out key molecular descriptors influencing benzenosulfonamide’s activity.