19077-98-6

Basic information

• Product Name: 4'-(2-pyridylsulphamoyl)acetanilide
• Synonyms: N-acetylsulfapyridine;2-(N4-ACETYLSULPHANILAMIDO)PYRIDINE;4'-(2-Pyridylsulfamoyl)acetanilide;N-[4-[(2-Pyridinylamino)sulfonyl]phenyl]acetamide;N4-Acetylsulfapyridine;2-(N4-Acetylsulfanilamide)pyridine;2-(N4-Acetylsulfanilamido)pyridine;Acetamide, N-(4-((2-pyridinylamino)sulfonyl)phenyl)-
• CAS NO: 19077-98-6
• Molecular Formula: C₁₃H₁₃N₃O₃S
• Molecular Weight: 291.32562
• EINECS: 242-802-5
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Sulfur & Selenium Compounds;Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 19077-98-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 226-228?C
• Appearance: /
• Density: 1.3362 (rough estimate)
• Refractive Index: 1.6740 (estimate)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Water Solubility: 0.32g/L(37 oC)
• BRN: 269306
• CAS DataBase Reference: 4'-(2-pyridylsulphamoyl)acetanilide(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-(2-pyridylsulphamoyl)acetanilide(19077-98-6)
• EPA Substance Registry System: 4'-(2-pyridylsulphamoyl)acetanilide(19077-98-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 19077-98-6(Hazardous Substances Data)

Usage

Description

4'-(2-Pyridylsulphamoyl)acetanilide is a chemical compound with the molecular structure featuring a pyridine ring and an amide group. It is a white solid, which indicates its stable and crystalline nature. 4'-(2-pyridylsulphamoyl)acetanilide is known for being a major active metabolite related to the adverse effects of Sulfasalazine in human serum, suggesting its potential role in pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
4'-(2-Pyridylsulphamoyl)acetanilide is used as an active metabolite for its involvement in the adverse effects of Sulfasalazine, a medication used to treat various inflammatory conditions such as ulcerative colitis and rheumatoid arthritis. The compound's role in these adverse effects makes it a significant compound for further research and development in the pharmaceutical industry, potentially leading to improved drug formulations or understanding of drug interactions.
Used in Chemical Research:
As a white solid with specific chemical properties, 4'-(2-Pyridylsulphamoyl)acetanilide can be utilized in chemical research for studying the properties and reactions of compounds with similar structures. This can contribute to the development of new chemical processes, synthesis methods, or the creation of novel compounds with desired properties for various applications.
Used in Drug Metabolism Studies:
Given its association with the adverse effects of Sulfasalazine, 4'-(2-Pyridylsulphamoyl)acetanilide can be employed in drug metabolism studies to better understand how drugs are processed and metabolized within the human body. This knowledge can be crucial for the development of safer and more effective medications, as well as for predicting and managing potential side effects.

Upstream product

• 103-84-4 Acetanilid 
• 144-83-2 sulphapyridine 
• 108-24-7 acetic anhydride 
• 109-04-6 2-bromo-pyridine 
• 121-61-9 p-acetylaminobenzenesulfonamide 
• 504-29-0 2-aminopyridine 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 75-36-5 acetyl chloride 

Downstream Products

• 1395084-24-8 (E)-4-((4-hydroxy-3,5-dimethylphenyl)diazenyl)-N-(pyridin-2-yl)-benzenesulfonamide 
• 1395084-37-3 (E)-4-((2-amino-3-chloro-4-hydroxy-5-methylphenyl)diazenyl)-N-(pyridin-2-yl)benzenesulfonamide 
• 1395084-38-4 (E)-4-((2-amino-4-hydroxy-3,5-dimethylphenyl)diazenyl)-N-(pyridin-2-yl)benzenesulfonamide 
• 1395084-25-9 (E)-4-((2-amino-4-hydroxy-5-methylphenyl)diazenyl)-N-(pyridin-2-yl)benzenesulfonamide 

Relevant articles and documents

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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.

Method for synthesizing salazosulfapyridine by utilizing 2-aminopyridine as raw material

The invention discloses a method for synthesizing salazosulfapyridine by utilizing 2-aminopyridine as a raw material. The method comprises the steps: step 1, performing a sulfamation reaction on 2-aminopyridine and para-acetylaminobenzene sulfonyl chloride in an aqueous solution of potassium carbonate; step 2, firstly performing hydrolyzation in DMSO-water mixed solution of sodium hydroxide, and then performing hydrochloric acid acidification; step 3, performing a diazo-reaction in an aqueous solution dissolving hydrochloric acid and sodium nitrite; step 4, performing a coupling reaction on diazonium salt and salicylic acid in an aqueous solution of sodium hydroxide. According to the method for synthesizing salazosulfapyridine by utilizing the 2-aminopyridine as the raw material, the 2-aminopyridine is taken as a starting raw material, and then is sequentially subjected to the sulfamation reaction, the hydrolyzation, the acidification, the diazo-reaction and the coupling reaction to obtain the salazosulfapyridine. The diazo-reaction and the coupling reaction have high conversation rate and a few side reaction so as to improve the purity of products and ensure the efficiency; furthermore, the source of the 2-aminopyridine is easy, the production cost is reduced, and the industrial production cost is large.