19837-81-1

Basic information

• Product Name: 4-AMINO-N-(3-CHLORO-PHENYL)-BENZENESULFONAMIDE
• Synonyms: benzenesulfonamide, 4-amino-N-(3-chlorophenyl)-
• CAS NO: 19837-81-1
• Molecular Formula: C₁₂H₁₁ClN₂O₂S
• Molecular Weight: 282.75
• Mol File: 19837-81-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 467 °C at 760 mmHg
• Flash Point: 236.3 °C
• Appearance: /
• Density: 1.466 g/cm³
• Vapor Pressure: 6.73E-09mmHg at 25°C
• Refractive Index: 1.674
• CAS DataBase Reference: 4-AMINO-N-(3-CHLORO-PHENYL)-BENZENESULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-N-(3-CHLORO-PHENYL)-BENZENESULFONAMIDE(19837-81-1)
• EPA Substance Registry System: 4-AMINO-N-(3-CHLORO-PHENYL)-BENZENESULFONAMIDE(19837-81-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 19837-81-1(Hazardous Substances Data)

Usage

General Description

4-AMINO-N-(3-CHLORO-PHENYL)-BENZENESULFONAMIDE is a chemical compound with the molecular formula C12H11ClN2O2S. It is a sulfonamide derivative with an amino group and a chlorophenyl group attached to the benzene ring. 4-AMINO-N-(3-CHLORO-PHENYL)-BENZENESULFONAMIDE is commonly used as a pharmaceutical ingredient in the production of drugs with antibacterial and diuretic properties. It works by inhibiting the growth of bacteria and promoting the excretion of excess water and salts from the body. 4-AMINO-N-(3-CHLORO-PHENYL)-BENZENESULFONAMIDE is an important component in the synthesis of medications used to treat urinary tract infections, high blood pressure, and other related conditions.

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

Upstream product

• 19837-98-0 N-acetyl-sulfanilic acid-(3-chloro-anilide) 
• 103-84-4 Acetanilid 
• 108-42-9 3-chloro-aniline 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 16937-05-6 3'-chloro-4-nitrobenzenesulfonanilide 

Downstream Products

• 114853-98-4 1,3-dihydro-5-1-(m-chlorophenyl)-p-sulphamylbenzeneazo>-1-(2'-naphthyl)-3-phenyl-2-thioxo-2H,5H-pyrimidine-4,6-dione 
• 114854-12-5 1,3-dihydro-5-1-(m-chlorophenyl)-p-sulphamylbenzeneazo>-1-(2'-naphthyl)-3-(p-tolyl)-2-thioxo-2H,5H-pyrimidine-4,6-dione 
• 1258977-91-1 6-hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro[1,7]phenanthroline-3-carboxylic acid [4-(3-chlorophenylsulfamoyl)phenyl]amide 
• 1258977-79-5 6-chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro[1,7]phenanthroline-3-carboxylic acid [4-(3-chlorophenylsulfamoyl)phenyl]amide 
• 1262334-06-4 2-[(2,6-dichlorophenyl)amino]-N₁-(3-chlorophenyl)-N₄-phenylacetoxyacetamidobenzenesulfonamide 
• 444723-03-9 NU 6132 
• 116691-34-0 N-(3-Chloro-phenyl)-4-(8-hydroxy-quinolin-5-ylazo)-benzenesulfonamide 

Relevant articles and documents

Structure-activity relationships of agonists for the orphan G protein-coupled receptor GPR27

GPR27 belongs, with GPR85 and GPR173, to a small subfamily of three receptors called “Super-Conserved Receptors Expressed in the Brain” (SREB). It has been postulated to participate in key physiological processes such as neuronal plasticity, energy metabolism, and pancreatic β-cell insulin secretion and regulation. Recently, we reported the first selective GPR27 agonist, 2,4-dichloro-N-(4-(N-phenylsulfamoyl)phenyl)benzamide (I, pEC50 6.34, Emax 100%). Here, we describe the synthesis and structure-activity relationships of a series of new derivatives and analogs of I. All products were evaluated for their ability to activate GPR27 in an arrestin recruitment assay. As a result, agonists were identified with a broad range of efficacies including partial and full agonists, showing higher efficacies than the lead compound I. The most potent agonist was 4-chloro-2,5-difluoro-N-(4-(N-phenylsulfamoyl)phenyl)benzamide (7y, pEC50 6.85, Emax 37%), and the agonists with higher efficacies were 4-chloro-2-methyl-N-(4-(N-phenylsulfamoyl)phenyl)benzamide (7p, pEC50 6.04, Emax 123%), and 2-bromo-4-chloro-N-(4-(N-phenylsulfamoyl)phenyl)benzamide (7r, pEC50 5.99, Emax 123%). Docking studies predicted the putative binding site and interactions of agonist 7p with GPR27. Selected potent agonists were found to be soluble and devoid of cellular toxicity within the range of their pharmacological activity. Therefore, they represent important new tools to further characterize the (patho)physiological roles of GPR27.

Synthesis, structural, biological and in silico studies of new 5-arylidene-4-thiazolidinone derivatives as possible anticancer, antimicrobial and antitubercular agents

A new series of halogenated 4-thiazolidinone derivatives bearing the sulfonamide moiety was synthesized and characterized via FT-IR, 1H NMR, 13C NMR, HRMS and single crystal X-ray analysis. The newly synthesized target compounds were screened for their in vitro cytotoxicity on the HepG2 and MDA-MB-231 cell lines, and antimicrobial and antitubercular activity. The compounds showed promising anticancer activity towards the MDA-MB-231 cell line, and the trichloro derivatives with p-chloro substitution (6i) and p-hydroxy substitution (7e) exhibited excellent anticancer activity. Compounds 6b and 7c were observed to be moderate antimicrobial agents. The seven most potent anticancer agents were further studied for their antitubercular activity against an M. tuberculosis strain and it was found that compound 7e showed significant antitubercular activity. The potent candidates were also tested for hemolysis activity against human RBC cells and were found to be non-toxic. The mode of action for the observed anticancer activity was further supported by molecular docking studies of the potent compounds against the enzyme Aurora kinase (PDB ID: 4ZTR). Molecular dynamics (MD) simulations were further performed to study the stability of the ligand-protein complex.