80-21-7

Basic information

• Product Name: 3-Aminobenzenesulfonanilide
• Synonyms: 3-AMINOBENZENESULFONANILIDE;M-AMINO BENZENE SULFONANILIDE;3-amino-n-phenyl-benzenesulfonamid;3-aminobenzenesulphonanilide;m-aminobenzenesulphonanilide;3-Aminobenzene sulfanilide;3-Aminosulfonanilide;Metanilanilide
• CAS NO: 80-21-7
• Molecular Formula: C₁₂H₁₂N₂O₂S
• Molecular Weight: 248.3
• EINECS: 201-259-4
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 80-21-7.mol

Chemical Properties

• Boiling Point: 458.9 °C at 760 mmHg
• Flash Point: 231.3 °C
• Appearance: /
• Density: 1.373 g/cm³
• Vapor Pressure: 1.32E-08mmHg at 25°C
• Refractive Index: 1.669
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 3-Aminobenzenesulfonanilide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Aminobenzenesulfonanilide(80-21-7)
• EPA Substance Registry System: 3-Aminobenzenesulfonanilide(80-21-7)

Safety Data

• Hazardous Substances Data: 80-21-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Aminobenzenesulfonanilide is used as an intermediate in the synthesis of various pharmaceuticals due to its chemical properties and reactivity. Its role in the production of drugs is significant, contributing to the development of new medications.
Used in Dye Production:
In the dye industry, 3-Aminobenzenesulfonanilide serves as an important intermediate. Its chemical structure allows for the creation of a range of dyes with specific color properties, making it valuable for various applications requiring colorants.
Used in Antimicrobial Applications:
Given its classification within the sulfonamides, 3-Aminobenzenesulfonanilide exhibits antimicrobial properties. It can be utilized in applications where resistance to microbial growth is necessary, such as in certain medical or industrial settings.

InChI:InChI=1/C12H12N2O2S/c13-10-5-4-8-12(9-10)17(15,16)14-11-6-2-1-3-7-11/h1-9,14H,13H2

Upstream product

• 23905-46-6 3-acetamidobenzene-1-sulfonyl chloride 
• 85169-25-1 3-acetylamino-benzenesulfonic acid anilide 
• 28791-26-6 3-nitro-N-phenylbenzenesulfonamide 

Downstream Products

• 110194-22-4 3-oxo-3-phenyl-propionic acid-(3-phenylsulfamoyl-anilide) 
• 1019851-51-4 2-chloro-N-[3-(anilinyl-1-sulfonyl)phenyl]acetamide 
• 120856-28-2 2-(4-diethylamino-2-methyl-phenylimino)-3-oxo-3-phenyl-propionic acid-(3-phenylsulfamoyl-anilide) 

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.

THERAPEUTIC COMPOUNDS AND COMPOSITIONS

Provided are aryl sulfonamide diarylurea derivative compounds that are inhibitors of mutant isocitrate dehydrogenase 1/2 (IDH 1/2), useful for treating cancer. Also provided are methods of treating cancer comprising administering to a subject in need thereof a compound described herein. Cancers that are treatable by the compounds of the invention are glioblastoma, myelodysplastic syndrome, myeloproliferative neoplasm, acute myelogenous leukemia, sarcoma, melanoma, non-small cell lung cancer, chondrosarcoma, and non-Hodgkin's lymphoma (NHL).

Synthesis and anticandidal activity of azole-containing sulfonamides

Twenty five benzenesulfonamides containing one imidazole or triazole ring, or two imidazole or triazole rings have been synthesized and evaluated as anticandidal agents. The most active compounds were 5c, 6b, 6c, 6e, and 17b, which exhibited MIC values of 4.55-24.39 mM depending on the clinical isolate. Comparing imidazole to triazole derivatives did not show a clear effect on activity. Compounds containing a N-benzyl group also showed no clear evidence on activity given the fact that they have an extra aromatic ring. Secondary sulfonamides, 5l, 5m, and 5n showed activities that were proportional to their lipophilicity. The activities of N-aryl-substituted derivatives 5j, 5k, 5l, 5m, 5n, and 6j were also proportional to their lipophilicity. Halogenation enhanced the activity as a result of improvement of lipophilicity. The presence of two imidazole or triazole rings in the same compound did not show a clear enhancement of activity.

2-Anilino-4-(Heterocyclic) Amino-Pyrimidines

The present invention relates to 2-arylamino-4-(heterocyclic)aminopyrimidines inhibitors which are inhibitors and therefore inhibit Protein Kinase C-alpha (PKC-α). The PKC-α inhibitors of the present invention are important for improving myocardial intracellular calcium cycling, resulting in improved myocardial contraction and relaxation performance and thereby slowing the progression of heart failure. The present invention further relates to compositions comprising said 2-arylamino-4-(heterocyclic)amino-pyrimidines and to methods for controlling, abating, or otherwise slowing the progression of heart failure.