77198-99-3

Usage

InChI:InChI=1/C14H15NO2S/c16-18(17,14-9-5-2-6-10-14)15-12-11-13-7-3-1-4-8-13/h1-10,15H,11-12H2

Upstream product

• 140-29-4 phenylacetonitrile 
• 873-55-2 sodium benzenesulfonate 
• 64-04-0 phenethylamine 
• 60-12-8 2-phenylethanol 
• 29281-83-2 4-methylbenzensulphonamide potassium salt 
• 98-10-2 benzenesulfonamide 
• 670-98-4 methyl benzenesulfinate 
• 98-11-3 benzenesulfonic acid 
• 92200-24-3 2-phenyl-N-(phenylsulfonyl)acetamide 
• 98-09-9 benzenesulfonyl chloride 

Downstream Products

• 110011-06-8 2-Benzenesulfonyl-1-(4-chloro-phenyl)-1,2,3,4-tetrahydro-isoquinoline 
• 110011-02-4 2-Benzenesulfonyl-1-methyl-1,2,3,4-tetrahydro-isoquinoline 
• 175287-91-9 2-benzenesulfonyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid ethyl ester 
• 72131-28-3 N-(4-hydroxyphenethyl)benzenesulfonamide 
• 618-41-7 Benzenesulfinic acid 
• 1415586-20-7 C₁₇H₂₀N₂O₄S 
• 81114-41-2 1-benzenesulfonyl-2,3-dihydro-1H-indole 
• 1071493-68-9 C₁₄H₁₄INO₂S 
• 73355-73-4 N-methyl-N-phenethyl-N'-phenyl-urea 
• 73355-76-7 N-methyl-N'-[1]naphthyl-N-phenethyl-urea 
• 88612-00-4 3,4-dihydro-isoquinoline-1-carboxylic acid ethyl ester 
• 50458-78-1 ethyl isoquinoline-1-carboxylate 

Relevant academic research and scientific papers

A kinetic analysis of the effects of β-phenylethylamine on the concentrations of dopamine and its metabolites in the rat striatum

The purpose of this investigation was to determine whether the increase in the dopamine (DA) concentration in the rat striatum after a rapid iv injection of β-phenylethylamine (PEA) can be quantitatively explained by the alteration of the striatum PEA con

Modulators of hERAP2 discovered by high-throughput screening

Endoplasmic reticulum aminopeptidase 2, ERAP2, is an emerging pharmacological target in cancer immunotherapy and control of autoinflammatory diseases, as it is involved in antigen processing. It has been linked to the risk of development of spondyloarthritis, and it associates with the immune infiltration of tumours and strongly predicts the overall survival for patients receiving check-point inhibitor therapy. While some selective inhibitors of its homolog ERAP1 are available, no selective modulator of ERAP2 has been disclosed so far. In order to identify such compounds, we screened an in-house focused library of 1920 compounds designed to target metalloenzymes. Structure-Activity Relationships and docking around two hits led to the discovery of selective inhibitors of ERAP2. Amid those, some bind to yet untapped amino-acids in the S1 pocket. Importantly, we disclose also the first activator of small substrates hydrolysis by ERAP2. Inhibitors and activators identified in this study could serve as useful starting points for optimization.

A Novel Method for Preparation of 2-Chloro Enesulfonamides

A novel method for the synthesis of 2-chloro enesulfonamides via the one-pot addition-elimination of N-chloro-N-fluorobenzenesulfonamides (CFBSA) to styrenes in the presence of Et3N is described. A total of 20 examples are presented to illustrate this concept including various of styrenes.

Metal-free direct construction of sulfonamides via iodine- mediated coupling reaction of sodium sulfinates and amines at room temperature

A simple, practical, and metal-free protocol has been developed for the synthesis of sulfonamides from sodium sulfinates and various amines through an iodine-mediated SN bond formation reaction at room temperature. This green reaction is cost-effective, operationally straightforward, and especially proceeds under very mild conditions to afford the target products in good to excellent yields (up to 98%).

Highly efficient one-pot synthesis of N-alkyl sulfonamides from alcohols using N-(p-toluenesulfonyl) imidazole (Tsim)

A facile and efficient method for one-pot synthesis of N-alkyl sulfonamides from alcohols using N-(p-toluenesulfonyl)imidazole (TsIm) is described. In this protocol, treatment of various potassium sulfonylamide salts and alcohols in the presence of TsIm and triethylamine in refluxing DMF furnishes the corresponding N-alkyl sulfonamides in good to excellent yields. This methodology is highly efficient for reaction of various structurally diverse primary and secondary alcohols as well as potassium sulfonylamides. Also, the density functional theoretical calculations are employed to mechanistically study this protocol. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental files: Additional text and figures.]

N-SUBSTITUTED-N-PHENYLETHYLSULFONAMIDES FOR THE IDENTIFICATION OF BIOLOGICAL AND PHARMACOLOGICAL ACTIVITY

Novel compounds are continually sought after to treat and prevent diseases and disorders. The invention relates to N-substituted-N-phenylethylsulfonamides useful for being biologically and pharmacologically screened, and to contribute to the exploration and identification of new lead molecules that are capable of modulating the functional activity of a biological target.

Design and synthesis of procollagen C-proteinase inhibitors

Non-peptidic inhibitors of procollagen C-proteinase (PCP) were designed from substrate leads. Compounds were optimized for potency and selectivity, with N-substituted aryl sulfonamide hydroxamates having the best combination of these properties. Compounds

LIBRARIES OF N-SUBSTITUTED-N-PHENYLETHYLSULFONAMIDES FOR DRUG DISCOVERY

New compounds are continually being sought for the treatment and prevention of disorders. The invention relates to N-substituted-N-phenylethylsulfonamides libraries which can be used in the search for, and identification of, new lead compounds that could

Discovery and mechanistic studies of a general air-promoted metal-catalyzed aerobic n- alkylation reaction of amides and amines with alcohols

The thermodynamically unfavorable anaerobic dehydrogenative alcohol activation to aldehydes and hydridometal species is found to be the bottleneck in metal-catalyzed N-alkylations due to a general and unnoticed catalyst deactivation by amines/amides. Thus, different from the anaerobic dehydrogenation process in borrowing hydrogen or hydrogen autotransfer reactions that require noble metal complexes or addition of capricious ligands for catalyst activation, the water-producing, exothermic, metal-catalyzed aerobic alcohol oxidation is thermodynamically more favorable and the most effective and advantageous aldehyde generation protocol. This leads to a general and advantageous air-promoted metal-catalyzed aerobic N-alkylation methodology that effectively uses many simpler, less expensive, more available, and ligand-free metal catalysts that were inactive under typical anaerobic borrowing hydrogen conditions, avoiding the use of preformed metal complexes and activating ligands and the exclusive requirement of inert atmosphere protection. This aerobic method is quite general in substrate scope and tolerates various amides, amines, and alcohols, revealing its potentially broad utilities and interests in academy and industry. In contrast to the commonly accepted borrowing hydrogen mechanism, based on a thorough mechanistic study and supported by the related literature background, a new mechanism analogous to the relay race game that has never been proposed in metal-catalyzed N-alkylation reactions is presented.

One-pot synthesis of sulfonamides from methyl sulfinates using ultrasound

Room temperature ultrasonic irradiation of neat mixtures of methyl sulfinates and primary or secondary amines (1.5 equiv) produced sulfinamides, which on m-CPBA oxidation (in dichloromethane) were converted into the corresponding sulfonamides. The two steps can be accomplished in one pot, in good overall yields, when using secondary amines, but primary amines give better sulfonamide yields when the peracid oxidation is effected on the purified sulfinamide. This constitutes a mild, efficient, and potentially scalable route to sulfonamides, which obviates the use of water sensitive, often lachrymatory sulfonyl chlorides and large reagent excesses.