63826-12-0

Basic information

• Product Name: 4-AMINO-N-METHYL-N-PHENYL-BENZENESULFONAMIDE
• Synonyms: 4-AMINO-N-METHYL-N-PHENYL-BENZENESULFONAMIDE;AKOS BBB/034
• CAS NO: 63826-12-0
• Molecular Formula: C₁₃H₁₄N₂O₂S
• Molecular Weight: 262.32746
• Mol File: 63826-12-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 139-140 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Boiling Point: 440.3°C at 760 mmHg
• Flash Point: 220.1°C
• Appearance: /
• Density: 1.315g/cm³
• Vapor Pressure: 5.97E-08mmHg at 25°C
• Refractive Index: 1.646
• PKA: 1.93±0.10(Predicted)
• CAS DataBase Reference: 4-AMINO-N-METHYL-N-PHENYL-BENZENESULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-N-METHYL-N-PHENYL-BENZENESULFONAMIDE(63826-12-0)
• EPA Substance Registry System: 4-AMINO-N-METHYL-N-PHENYL-BENZENESULFONAMIDE(63826-12-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 63826-12-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H14N2O2S/c1-15(12-5-3-2-4-6-12)18(16,17)13-9-7-11(14)8-10-13/h2-10H,14H2,1H3

Upstream product

• 332886-16-5 N-(4-(N-methyl-N-phenylsulfamoyl)phenyl)acetamide 
• 107145-69-7 N-dichlorophosphoryl-sulfanilyl chloride 
• 100-61-8 N-methylaniline 
• 64999-94-6 N-methyl-N-phenyl-4-nitrobenzene sulphonamide 
• 1576-44-9 N-nosylaniline 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 62-53-3 aniline 

Downstream Products

• 94243-25-1 4-(Cyanomethyl-amino)-N-methyl-N-phenyl-benzenesulfonamide 
• 88327-92-8 [4-(Methyl-phenyl-sulfamoyl)-phenylamino]-acetic acid 
• 94243-31-9 C₁₅H₁₄N₄O₃S 
• 88323-72-2 6,7,8,9-Tetrahydro-5H-carbazole-3-sulfonic acid methyl-phenyl-amide 
• 88327-98-4 C₁₅H₁₅N₃O₅S 
• 88323-66-4 1-[4-(Methyl-phenyl-sulfamoyl)-phenyl]-1H-pyrazole-3,4-dicarboxylic acid dimethyl ester 
• 88323-80-2 4-(3,4-Dibenzoyl-pyrazol-1-yl)-N-methyl-N-phenyl-benzenesulfonamide 
• 88323-83-5 N-Methyl-N-phenyl-4-sulfonamidophenylhydrazin 
• 919116-77-1 N-methyl-4-(4-methylsulphanyl-5-trifluoromethylpyrimidin-2-ylamino)-N-phenylbenzenesulphonamide 

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.

Design, synthesis and biological evaluation of GPR55 agonists

GPR55, a G protein-coupled receptor, is an attractive target to alleviate inflammatory and neuropathic pain and treat osteoporosis and cancer. Identifying a potent and selective ligand will aid to further establish the specific physiological roles and pharmacology of the receptor. Towards this goal, a targeted library of 22 compounds was synthesized in a modular fashion to obtain structure-activity relationship information. The general route consisted of coupling a variety of p-aminophenyl sulfonamides to isothiocyanates to form acylthioureas. For the synthesis of a known naphthyl ethyl alcohol motif, route modification led to a shorter and more efficient process. The 22 analogues were analyzed for their ability to serve as agonists at GPR55 and valuable information for both ends of the molecule was ascertained.

2,4-diamino-pyrimidines as aurora inhibitors

The present invention encompasses compounds of general formula (1) wherein R1 to R3 are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and the use thereof for preparing a pharmaceutical composition having the above-mentioned properties.