101252-53-3

Basic information

• Product Name: 4-(aminomethyl)-N-methylbenzenesulfonamide
• Synonyms: 4-(aminomethyl)-N-methylbenzenesulfonamide
• CAS NO: 101252-53-3
• Molecular Formula: C₈H₁₂N₂O₂S
• Molecular Weight: 200.26
• Mol File: 101252-53-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 98-99 °C
• Boiling Point: 351.3±44.0 °C(Predicted)
• Appearance: /
• Density: 1.251±0.06 g/cm3(Predicted)
• PKA: 11.59±0.30(Predicted)
• CAS DataBase Reference: 4-(aminomethyl)-N-methylbenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(aminomethyl)-N-methylbenzenesulfonamide(101252-53-3)
• EPA Substance Registry System: 4-(aminomethyl)-N-methylbenzenesulfonamide(101252-53-3)

Safety Data

• Hazardous Substances Data: 101252-53-3(Hazardous Substances Data)

Upstream product

• 864528-61-0 4-(azidomethyl)-N-methylbenzenesulfonamide 
• 49584-26-1 p-cyanobenzenesulfonyl chloride 
• 148459-00-1 4-(bromomethyl)-N-methylbenzenesulfonamide 
• 66176-39-4 4-(bromomethyl)benzene-1-sulfonyl chloride 
• 623-00-7 4-bromobenzenecarbonitrile 
• 150993-53-6 4-(benzylsulfanyl)benzonitrile 
• 56236-82-9 4-cyano-N-methylbenzenesulfonamide 

Downstream Products

• 1194019-19-6 6-bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide 
• 1194017-72-5 1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide 
• 1194019-31-2 1-(4-fluoro-phenyl)-6-methyl-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide 
• 1194019-29-8 1-(4-fluoro-phenyl)-6-hydroxy-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide 
• 1194019-25-4 6-cyano-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide 
• 1194019-33-4 1-(4-fluoro-phenyl)-6-methylamino-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide 
• 1194019-27-6 1-(4-fluoro-phenyl)-6-methanesulfonyl-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide 
• 1194019-45-8 1-(4-fluoro-phenyl)-1H-indazole-4,6-dicarboxylic acid 6-methylamide 4-(4-methylsulfamoyl-benzylamide) 
• 1194019-43-6 1-(4-fluoro-phenyl)-4-(4-methylsulfamoyl-benzylcarbamoyl)-1H-indazole-6-carboxylic acid 
• 1194019-41-4 1-(4-fluoro-phenyl)-4-(4-methylsulfamoyl-benzylcarbamoyl)-1H-indazole-6-carboxylic acid ethyl ester 

Relevant articles and documents

Discovery of carboxyl-containing biaryl ureas as potent RORγt inverse agonists

GSK805 (1) is a potent RORγt inverse agonist, but a drawback of 1 is its low solubility, leading to a limited absorption in high doses. We have explored detailed structure-activity relationship on the amide linker, biaryl and arylsulfonyl moieties of 1 trying to improve solubility while maintaining RORγt activity. As a result, a novel series of carboxyl-containing biaryl urea derivatives was discovered as potent RORγt inverse agonists with improved drug-like properties. Compound 3i showed potent RORγt inhibitory activity and subtype selectivity with an IC50 of 63.8 nM in RORγ FRET assay and 85 nM in cell-based RORγ-GAL4 promotor reporter assay. Reasonable inhibitory activity of 3i was also achieved in mouse Th17 cell differentiation assay (76percent inhibition at 0.3 μM). Moreover, 3i had greatly improved aqueous solubility at pH 7.4 compared to 1, exhibited decent mouse PK profile and demonstrated some in vivo efficacy in an imiquimod-induced psoriasis mice model.

Discovery of carbazole carboxamides as novel RORγt inverse agonists

A novel series of carbazole carboxamides was discovered as potent RORγt inverse agonists using a scaffold hybridization strategy. Structure-activity relationship exploration on the amide linker, carbazole ring and arylsulfone moiety of the hybrid amide 3a led to identification of potent RORγt inverse agonists. Compound 6c was found to have a good RORγt activity with an IC50 of 58.5 nM in FRET assay, and reasonable inhibitory activity in mouse Th17 cell differentiation assay (58.8% inhibition at 0.3 μM). The binding mode of carbazole carboxamides in RORγt ligand binding domain was discussed.

ISOINDOLINE INHIBITORS OF ROR-GAMMA

Provided are novel compounds of Formula (I): pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are useful in the treatment of diseases and disorders mediated by RORγ. Also provided are pharmaceutical compositions comprising the novel compounds of Formula (I) and methods for their use in treating one or more inflammatory, metabolic, autoimmune and other diseases or disorders.