220166-48-3

Basic information

• Product Name: 4-methoxy-N-(2-{[(4-methoxyphenyl)sulfonyl]amino}phenyl)benzenesulfonamide
• Synonyms: 4-methoxy-N-(2-{[(4-methoxyphenyl)sulfonyl]amino}phenyl)benzenesulfonamide
• CAS NO: 220166-48-3
• Molecular Formula: C₂₀H₂₀N₂O₆S₂
• Molecular Weight: 448.5126
• Mol File: 220166-48-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-methoxy-N-(2-{[(4-methoxyphenyl)sulfonyl]amino}phenyl)benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methoxy-N-(2-{[(4-methoxyphenyl)sulfonyl]amino}phenyl)benzenesulfonamide(220166-48-3)
• EPA Substance Registry System: 4-methoxy-N-(2-{[(4-methoxyphenyl)sulfonyl]amino}phenyl)benzenesulfonamide(220166-48-3)

Safety Data

• Hazardous Substances Data: 220166-48-3(Hazardous Substances Data)

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 98-68-0 4-methoxy-phenyl-sulphonyl chloride 

Downstream Products

• 220165-50-4 1,4-ditosyl-2-vinyl-1,2,3,4-tetrahydroquinoxaline 
• 220167-11-3 1,2,3,4-tetrahydro-2-vinylquinoxaline 
• 49633-27-4 2-hydroxymethyl-1,4-bis-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-quinoxaline 

Relevant articles and documents

Bis(sulfonamide) transmembrane carriers allow pH-gated inversion of ion selectivity

Bis(sulfonamide) based synthetic carriers are reported for inversion of ion selectivity upon deviation of pH within a narrow window. A liposomal membrane potential is also generated when potassium ions are passively transported by these carriers.

Aryl Bis-Sulfonamide Inhibitors of IspF from Arabidopsis thaliana and Plasmodium falciparum

2-Methylerythritol 2,4-cyclodiphosphate synthase (IspF) is an essential enzyme for the biosynthesis of isoprenoid precursors in plants and many human pathogens. The protein is an attractive target for the development of anti-infectives and herbicides. Using a photometric assay, a screen of 40 000 compounds on IspF from Arabidopsis thaliana afforded symmetrical aryl bis-sulfonamides that inhibit IspF from A. thaliana (AtIspF) and Plasmodium falciparum (PfIspF) with IC50 values in the micromolar range. The ortho-bis-sulfonamide structural motif is essential for inhibitory activity. The best derivatives obtained by parallel synthesis showed IC50 values of 1.4 μm against PfIspF and 240 nm against AtIspF. Substantial herbicidal activity was observed at a dose of 2 kg ha-1. Molecular modeling studies served as the basis for an in silico search targeted at the discovery of novel, non-symmetrical sulfonamide IspF inhibitors. The designed compounds were found to exhibit inhibitory activities in the double-digit micromolar IC50 range.

Palladium(0)-catalyzed asymmetric synthesis of 1,2,3,4-tetrahydro-2- vinylquinoxalines

Reaction of (Z)-1,2-bis(methoxycarbonyloxy)but-2-ene (2) with various N,N-bis(arylsulfonyl)-o-phenylenediamines 1 was catalyzed by a palladium complex associated with chiral ligands to give optically active 1,4- bis(arylsulfonyl)-1,2,3,4-tetrahydro-2-vinylquinoxalines 3 with up to 62% ee. The use of (S)-MeOBIPHEP as the chiral ligand and N,N-bis(p-tolylsulfonyl)-o- phenylenediamine (1i) as the nucleophile led to the highest ee at 25 °C, regardless of the solvent used. The enantioselectivity of the cyclization is strongly affected by the nature of the substituents at the nitrogen atom.