349398-11-4

Basic information

• Product Name: Benzoic acid, 4-[[(4-nitrophenyl)sulfonyl]amino]-, methyl ester
• CAS NO: 349398-11-4
• Molecular Formula: C14H12N2O6S
• Molecular Weight: 336.325
• Mol File: 349398-11-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 4-[[(4-nitrophenyl)sulfonyl]amino]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-[[(4-nitrophenyl)sulfonyl]amino]-, methyl ester(349398-11-4)
• EPA Substance Registry System: Benzoic acid, 4-[[(4-nitrophenyl)sulfonyl]amino]-, methyl ester(349398-11-4)

Safety Data

• Hazardous Substances Data: 349398-11-4(Hazardous Substances Data)

Upstream product

• 63450-84-0 methyl 4-aminobenzoate hydrochloride 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 150-13-0 4-amino-benzoic acid 
• 619-45-4 4-methoxycarbonyl aniline 

Downstream Products

• 881005-27-2 methyl N-methyl-N-nosyl-p-aminobenzoate 
• 18358-63-9 methyl 4-(N-methyl)aminobenzoate 
• 3406-75-5 2-(4-nitrophenylthio)acetic acid 
• 63421-71-6 4-(4-nitrobenzenesulfonylamino)benzoic acid 

Relevant articles and documents

Discovery of a series of small molecules as potent histone deacetylase inhibitors

A series of small molecules were designed and synthesized based on our previous virtual screening approach, which was performed to discover potent histone deacetylase inhibitors (HDACIs) with novel structures. The derived compounds were tested by Hela cell nucleus extract for enzyme inhibition assay. Tumor cell growth inhibition assays were performed using a series of tumor cell lines. Molecule 4h has the best performance among these compounds with enzyme inhibition IC50 of 0.14 μM and tumor cell growth inhibition IC50 of 1.85 (U937), 2.02 (HL60), 2.67 (K562). Docking studies showed that multiple H-bonds and hydrophobic interactions make 4h binding to the active site of HDAC. 4h has the advantage of low molecular weight, so a variety of structural modifications can be performed in our further studies.

Solid-phase parallel synthesis and SAR of 4-amidofuran-3-one inhibitors of cathepsin S: Effect of sulfonamides P3 substituents on potency and selectivity

Highly potent and selective 4-amidofuran-3-one inhibitors of cathepsin S are described. The synthesis and structure-activity relationship of a series of inhibitors with a sulfonamide moiety in the P3 position is presented. Several members of the series show sub-nanomolar inhibition of the target enzyme as well as an excellent selectivity profile and good cellular potency. Molecular modeling of the most interesting inhibitors describes interactions in the extended S3 pocket and explains the observed selectivity towards cathepsin K.

Highly specific N-monomethylation of primary aromatic amines

A synthetic methodology for the specific conversion of primary aromatic amines into their N-monomethyl derivatives under very mild conditions is presented. Anilines are treated with 4-nitrobenzenesulfonyl (nosyl) chloride to generate the corresponding sulfonamides 2 in high yields. The subsequent N-methylation reaction of the sulfonamides 2 with a solution of diazomethane is rapid and quantitative. Removal of the nosyl protecting group is readily carried out using the reagent system mercaptoacetic acid/1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) affording the N-monomethylated aromatic amines 4. The procedure is convenient, efficient, and gives rise to the N-monomethyl-anilines exclusively.