85169-25-1

Basic information

• Product Name: N-[3-[(phenylamino)sulphonyl]phenyl]acetamide
• Synonyms: N-[3-[(phenylamino)sulphonyl]phenyl]acetamide;N-[3-[(Phenylamino)sulfonyl]phenyl]acetamide;Einecs 285-967-9
• CAS NO: 85169-25-1
• Molecular Formula: C₁₄H₁₄N₂O₃S
• Molecular Weight: 290.33756
• EINECS: 285-967-9
• Mol File: 85169-25-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.371g/cm³
• Refractive Index: 1.647
• CAS DataBase Reference: N-[3-[(phenylamino)sulphonyl]phenyl]acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[3-[(phenylamino)sulphonyl]phenyl]acetamide(85169-25-1)
• EPA Substance Registry System: N-[3-[(phenylamino)sulphonyl]phenyl]acetamide(85169-25-1)

Safety Data

• Hazardous Substances Data: 85169-25-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H14N2O3S/c1-11(17)15-13-8-5-9-14(10-13)20(18,19)16-12-6-3-2-4-7-12/h2-10,16H,1H3,(H,15,17)

Upstream product

• 23905-46-6 3-acetamidobenzene-1-sulfonyl chloride 
• 62-53-3 aniline 

Downstream Products

• 80-21-7 1-aminobenzene-3-sulphonic acid phenylamide 

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.