65588-60-5

Upstream product

• 70-55-3 toluene-4-sulfonamide 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 5763-61-1 3,4-dimethoxybenzylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 100371-00-4 N-veratryl-β-alanine 
• 100253-85-8 N-veratryl-β-alanine nitrile 
• 102011-24-5 N-(toluene-4-sulfonyl)-N-veratryl-β-alanine 

Downstream Products

• 787571-89-5 N-(4-benzyloxy-3,5-dimethylphenethyl)-N-tosyl-3,4-dimethoxybenzylamine 
• 1527501-78-5 N-(3,4-dimethoxybenzyl)-N-(1H-indol-2-yl)-4-methylbenzenesulfonamide 
• 1431115-78-4 N-allyl-N-(3,4-dimethoxybenzyl)-4-methylbenzenesulfonamide 
• 1431116-78-7 (3S,4R,5R)-3-[3-(tert-butyldiphenylsilyloxy)propyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2,5-methano-1H-2-benzazepin-4-yl acetate 
• 1431116-72-1 (3S,4R,5R)-4-(benzyloxy)-3-[3-(benzyloxy)propyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-2,5-methano-1H-2-benzazepine 
• 1431116-60-7 methyl (2E)-3-{(3S,4R,5S)-3-[3-(benzyloxy)propyl]-4-hydroxy-7,8-dimethoxy-2-tosyl-2,3,4,5-tetrahydro-1H-2-benzazepin-5-yl}acrylate 
• 1431116-54-9 N-[(4S,2E)-7-(benzyloxy)-1-hydroxy-2-hepten-4-yl]-N-(3,4-dimethoxybenzyl)-4-methylbenzenesulfonamide 
• 1431116-48-1 (S)-N-{5-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)pentan-2-yl}-N-(3,4-dimethoxybenzyl)-4-methylbenzenesulfonamide 
• 1431115-84-2 N-[(3E)-5-hydroxy-3-pentenyl]-N-(3,4-dimethoxybenzyl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

A synthetic N-alkyl sulfonamide derivatives

The invention discloses a method for synthesizing a N-alkyl sulfonamide derivative. The method comprises the following steps: adding a sulfonamide derivative, a water-soluble catalyst, an alkali, alcohol and a solvent into a reaction container; reacting the reaction mixture at 100-120 DEG C for several hours, cooling to room temperature; performing rotary evaporation to remove the solvent, and then separating by a column to obtain the target compound. The method of the invention starts from the sulfonamide derivative, and obtains the N-alkyl sulfonamide derivative through reaction with alcohol. The method of the invention adopts a water-soluble iridium complex as a catalyst; the reaction is carried out in water; and the target compound is obtained with a high yield. Therefore, the reaction meets the requirements for green chemistry, and the method has wide development prospects.

The N-alkylation of sulfonamides with alcohols in water catalyzed by the water-soluble iridium complex {Cp*[6,6'-(OH)2bpy](H 2O)}[OTf]2

The water-soluble iridium complex {Cp*[6,6'-(OH)2bpy] (H2O)}[OTf]2 (Cp=ν5-pentamethylcyclopentadienyl, bpy=2,2'-bipyridine) was found to be a general and highly efficient catalyst for the Nalkylation of the poor nucleophilic sulfonamides with alcohols as alkylating agents in water. The presence of OH units in the bpy ligand is crucially important for the catalytic activity of the iridium complex. Mechanistic investigations revealed that the catalytically active species is a ligand-metal bifunctional iridium complex bearing an N,N'-chelated 2,2'-bipyridinated ligand and an aqua ligand. Notably, the present catalytic system and the proposed mechanism provide a new horizon and scope for the development of "hydrogen autotransfer (or hydrogen-borrowing) processes".

CuI-catalyzed coupling of gem-dibromovinylanilides and sulfonamides: An efficient method for the synthesis of 2-amidoindoles and indolo[1,2-a] quinazolines

A Cu(I)-catalyzed, intermolecular protocol for the synthesis of 2-amidoindoles and tetrahydroindolo[1,2-a]quinazolines in shorter time and high yields is reported. The key highlight of this disclosure is the formation of 2-amidoindole and tetrahydroindolo[1,2-a]quinazoline moieties directly from gem-dibromovinylanilides and sulfonamides in a one-pot fashion through the in situ formation of ynamides followed by a base-promoted intramolecular hydroamidation.

Electron-withdrawing substituted benzenesulfonamides against the predominant community-associated methicillin-resistant Staphylococcus aureus strain USA300

A small focused chemical library constituted of sulfonamides was synthesized. These compounds were designed to lack the p-aminobenzene moiety typically found in sulfonamide antibiotics. Antimicrobial activities of these synthetic compounds were investigated against global predominant methicillin-resistant Staphylococcus aureus (MRSA) strain USA300 (SF8300) and control strains of Staphylococcus aureus (S. aureus) ATCC 25923 and ATCC 29213 using disk diffusion and microdilution assays. Based on susceptibility results, potent S. aureus and MRSA USA300 growth inhibitors such as N-[3,5- bis(trifluoromethyl)phenyl]-4-bromobenzenesulfonamide with minimum inhibitory concentration (MIC) as low as 5.6 μg/cm3 along with other effective sulfonamides were discovered. Structure-activity correlations revealed that these desamino-benzenesulfonamides required electron-withdrawing substituents to be effective inhibitors of bacterial pathogen growth. In addition, their ability to inhibit growth of S. aureus strains was retained even when bacterial folate synthetic intermediate, p-aminobenzoic acid (PABA), was supplemented, whereas PABA supplementation completely diminished the antibacterial activity of the known sulfa drug tested, sulfamethoxazole. The sulfa-resistant MRSA strain COL also showed great susceptibility to these desamino-benzenesulfonamides. These results imply a unique mechanism of growth inhibition by these potent desamino-benzenesulfonamides, different from the well-known folate pathway target of sulfonamide antibiotics.