19837-85-5

Basic information

• Product Name: 4-AMINO-N-(2-CHLORO-PHENYL)-BENZENESULFONAMIDE
• Synonyms: Sulfanilanilide,2'-chloro- (6CI,8CI);N-(2-Chlorophenyl) 4-aminobenzenesulfonamide
• CAS NO: 19837-85-5
• Molecular Formula: C₁₂H₁₁ClN₂O₂S
• Molecular Weight: 282.7459
• Mol File: 19837-85-5.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 463.8 °C at 760 mmHg
• Flash Point: 234.3 °C
• Appearance: /
• Density: 1.466 g/cm³
• Vapor Pressure: 8.8E-09mmHg at 25°C
• Refractive Index: 1.674
• CAS DataBase Reference: 4-AMINO-N-(2-CHLORO-PHENYL)-BENZENESULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-N-(2-CHLORO-PHENYL)-BENZENESULFONAMIDE(19837-85-5)
• EPA Substance Registry System: 4-AMINO-N-(2-CHLORO-PHENYL)-BENZENESULFONAMIDE(19837-85-5)

Safety Data

• Hazardous Substances Data: 19837-85-5(Hazardous Substances Data)

Usage

Description

4-AMINO-N-(2-CHLORO-PHENYL)-BENZENESULFONAMIDE is a chemical compound with the molecular formula C12H11ClN2O2S. It is a sulfonamide derivative that features an amino group and a chlorine-substituted phenyl group. 4-AMINO-N-(2-CHLORO-PHENYL)-BENZENESULFONAMIDE is widely recognized for its role in the pharmaceutical industry, where it serves as a key building block in the synthesis of a variety of pharmaceutical products, especially those targeting bacterial infections.

Uses

Used in Pharmaceutical Industry:
4-AMINO-N-(2-CHLORO-PHENYL)-BENZENESULFONAMIDE is used as an intermediate in the synthesis of pharmaceuticals for the treatment of bacterial infections. As a sulfonamide, it functions by inhibiting bacterial growth through the effective blocking of folic acid synthesis, which is crucial for the survival and proliferation of bacteria.
Used in Therapeutic Agent Development:
This chemical compound is also utilized in the development of therapeutic agents for the treatment of various diseases and conditions. Its potential as a therapeutic agent is attributed to its ability to target specific biological pathways and processes, offering a promising avenue for the development of new treatments and interventions in medicine.

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

Upstream product

• 103-84-4 Acetanilid 
• 95-51-2 o-chloroaniline 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 1219126-42-7 N-(2-chloro-4-iodophenyl)-4-nitrobenzenesulfonamide 
• 63132-66-1 N-(2-chlorophenyl)-4-nitrobenzenesulfonamide 
• 19838-03-0 4-acetylamino-N-(2-chlorophenyl)benzenesulfonamide 

Downstream Products

• 1432112-10-1 N-(2-chlorophenyl)-4-{[1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridin-3-yl]amino}benzenesulfonamide 
• 1262334-05-3 2-[(2,6-dichlorophenyl)amino]-N₁-(2-chlorophenyl)-N₄-phenylacetoxyacetamidobenzenesulfonamide 
• 1219125-96-8 N-(4-{[(2-chlorophenyl)amino]sulfonyl}phenyl)pyridine-2-carboxamide 
• 114854-11-4 1,3-dihydro-5-1-(o-chlorophenyl)-p-sulphamylbenzeneazo>-1-(2'-naphthyl)-3-(p-tolyl)-2-thioxo-2H,5H-pyrimidine-4,6-dione 
• 114853-97-3 1,3-dihydro-5-1-(o-chlorophenyl)-p-sulphamylbenzeneazo>-1-(2'-naphthyl)-3-phenyl-2-thioxo-2H,5H-pyrimidine-4,6-dione 
• 116691-35-1 N-(2-Chloro-phenyl)-4-(8-hydroxy-quinolin-5-ylazo)-benzenesulfonamide 

Relevant articles and documents

Design, synthesis and biological evaluation of novel naphthoquinone-4-aminobenzensulfonamide/carboxamide derivatives as proteasome inhibitors

A series of novel 4-aminobenzensulfonamide/carboxamide derivatives bearing naphthoquinone pharmacophore were designed, sythesized and evaluated for their proteasome inhibitory and antiproliferative activities against human breast cancer cell line (MCF-7). The structures of the synthesized compounds were confirmed by spectral and elemental analyses. The proteasome inhibitory activity studies were carried out using cell-based assay. The antiproteasomal activity results revealed that most of the compounds exhibited inhibitory activity with different percentages against the caspase-like (C-L, β1 subunit), trypsin-like (T-L, β2 subunit) and chymotrypsin-like (ChT-L, β5 subunit) activities of proteasome. Among the tested compounds, compound 14 bearing 5-chloro-2-pyridyl ring on the nitrogen atom of sulfonamide group is the most active compound in the series and displayed higher inhibition with IC50 values of 9.90 ± 0.61, 44.83 ± 4.23 and 22.27 ± 0.15 μM against ChT-L, C-L and T-L activities of proteasome compared to the lead compound PI-083 (IC50 = 12.47 ± 0.21, 53.12 ± 2.56 and 26.37 ± 0.5 μM), respectively. The antiproliferative activity was also determined by MTT (3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide) assay in vitro. According to the antiproliferative activity results, all of the compounds exhibited cell growth inhibitory activity in a range of IC50 = 1.72 ± 0.14–20.8 ± 0.5 μM and compounds 13 and 28 were found to be the most active compounds with IC50 values of 1.79 ± 0.21 and 1.72 ± 0.14 μM, respectively. Furthermore, molecular modeling studies were carried out for the compounds 13, 14 and 28 to investigate the ligand-enzyme binding interactions.

Synthesis, Computational Docking, and Antimycobacterial Study of Novel N'-phenyl-4-pyrrol-1-yl-benzenesulfonamide Derivatives

Fresh sequences of pyrrole linked N'-phenyl-4-pyrrolyl-benzenesulfonamide derivatives were synthesized by different synthetic methods. Synthesis of the N'-phenyl-4-(1H-pyrrol-1-yl) benzenesulfonamides 5(a-e)/4-(2,5-dimethyl-1H-pyrrol-1-yl)-N'-phenylbenzenesulfonamides 6(a-e) was achieved by refluxing 2,5-dimethoxytetrahydrofuran/hexane 2,5-dione separately in presence of acetic acid. Further, synthesis of N-(4-(N'-phenylsulfamoyl)phenyl)-4-(1H-pyrrol-1-yl)benzamides 8(a-b)/4-(2,5-dimethyl-1H-pyrrol-1-yl)-N-(4-(N'-phenylsulfamoyl)phenyl)benzamides 10(a-b) was achieved by cold stirring of 4-(1H-pyrrol-1-yl)benzoic acid (7)/2,5-dimethyl-1H-pyrrol-1-yl)benzoic acid (9) correspondingly in the presence of 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, N', N'-diisopropylethylamine, and Dimethylformamide. In vitro anti-tubercular study of afresh compounds has shown good minimum inhibitory concentration values (0.4-12.5 μg/mL) counter to Mycobacterium tuberculosis H37Rv, while the corresponding study of reported molecules for antibacterial activity disclosed considerable inhibition values (0.4-25 μg/mL) counter to Escherichia coli (Gram-ve) than Staphylococcus aureus (Gram +ve).

SMALL MOLECULE ACTIVATORS OF NICOTINAMIDE PHOSPHORIBOSYLTRANSFERASE (NAMPT) AND USES THEREOF

Provided herein are small molecule activators of Nicotinamide Phosphoribosyltransferase (NAMPT), compositions comprising the compounds, and methods of using the compounds and compositions.