19077-98-6

Usage

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

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

Downstream Products

• 51543-29-4 4-amino-N-methyl-N-pyridin-2-yl-benzenesulfonamide 
• 66507-93-5 4-acetylamino-N-(1-methyl-1H-pyridin-2-ylidene)-benzenesulfonamide 
• 66559-86-2 4-acetylamino-N-methyl-N-pyridin-2-yl-benzenesulfonamide 
• 144-83-2 sulphapyridine 
• 857621-40-0 N-acetyl-sulfanilic acid-(5-iodo-[2]pyridylamide) 
• 100395-14-0 N-acetyl-sulfanilic acid-(hydroxy-[2]pyridyl-amide) 
• 19250-23-8 N-acetyl-sulfanilic acid-(1-oxy-[2]pyridylamide) 
• 89463-71-8 N-[2]pyridyl-hydroxylamine 
• 19250-24-9 sulfanilic acid-(1-oxy-[2]pyridylamide) 
• 58944-05-1 4-amino-N-(1-methyl-1H-pyridin-2-ylidene)-benzenesulfonamide 
• 1395084-25-9 (E)-4-((2-amino-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 
• 1395084-37-3 (E)-4-((2-amino-3-chloro-4-hydroxy-5-methylphenyl)diazenyl)-N-(pyridin-2-yl)benzenesulfonamide 

Relevant academic research and scientific papers

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.

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.

A process for preparing 2 - (4 - acetamide benzene sulfonyl) amino pyridine method

The invention provides a method for preparing 2-(4-acetamidobenzenesulfonyl)amidopyridine, which comprises the following step: under the condition of not using any solvent, reacting p-acetylsulphanilyl chloride and excessive 2-aminopyridine to obtain the 2-(4-acetamidobenzenesulfonyl)amidopyridine. The method has the advantages of simple technique, high product purity, high yield and environment friendliness, and can implement clean production. The method can recover the raw materials, thereby saving the raw materials.

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.