6295-94-9

Usage

InChI:InChI=1/C14H15NO3S/c1-11-7-9-12(10-8-11)19(16,17)15-13-5-3-4-6-14(13)18-2/h3-10,15H,1-2H3

Upstream product

• 90-04-0 2-methoxy-phenylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 941-55-9 4-toluenesulfonyl azide 
• 5720-06-9 2-Methoxyphenylboronic acid 
• 127-65-1 chloroamine-T 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 578-57-4 2-bromoanisole 
• 70-55-3 toluene-4-sulfonamide 
• 21849-40-1 dibromamine-T 
• 103687-94-1 ethyl 3-(2-methoxyphenylamino)propanoate 
• 529-28-2 4-iodoanisol 
• 103687-95-2 ethyl β-(N-tosyl-o-anisidino)propionate 

Downstream Products

• 21268-85-9 2-amino-1-methoxy-3,5-dinitrobenzene 
• 106508-44-5 N-(2-methoxy-4-nitrophenyl)-4-methylbenzenesulfonamide 
• 17102-72-6 2-(p-Toluolsulfon-N-formylamido)-anisol 
• 155581-87-6 7,16-bis(2-methoxyphenyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane 
• 497968-92-0 1,10-bis(2-methoxyphenyl)-4,7-dioxa-1,10-diazadecane 
• 497968-93-1 7,13-bis(2-methoxyphenyl)-1,4,10-trioxa-7,13-diazacyclopentadecane-8,12-dione 
• 182926-58-5 7,13-bis(2-methoxyphenyl)-1,4,10-trioxa-7,13-diazacyclopentadecane 
• 497968-89-5 7-(2-methoxy-4-nitrophenyl)-13-(2-methoxyphenyl)-1,4,10-trioxa-7,13-diazacyclopentadecane 
• 497969-01-4 3-methoxy-4-[13-(2-methoxyphenyl)-1,4,10-trioxa-7,13-diazacyclopentadecan-7-yl]phenylamine 
• 497968-94-2 7,16-bis(2-methoxyphenyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane-6,17-dione 
• 497969-02-5 3-methoxy-4-[16-(2-methoxyphenyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecan-7-yl]phenylamine 
• 497968-90-8 7-(2-methoxy-4-nitrophenyl)-16-(2-methoxyphenyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane 
• 1097201-76-7 N-(2-methoxyphenyl)-N-tosylbenzamide 
• 1097201-87-0 N-(2-methoxyphenyl)-3,5-dinitro-N-(phenylsulfonyl)benzamide 

Relevant academic research and scientific papers

High-Throughput Discovery and Evaluation of a General Catalytic Method for N-Arylation of Weakly Nucleophilic Sulfonamides

Through targeted high-throughput experimentation (HTE), we have identified the Pd/AdBippyPhos catalyst system as an effective and general method to construct densely functionalized N,N-diaryl sulfonamide motifs relevant to medicinal chemistry. AdBippyPhos is particularly effective for the installation of heteroaromatic groups. Computational steric parametrization of the investigated ligands reveals the potential importance of remote steric demand, where a large cone angle combined with an accessible Pd center is correlated to successful catalysts for C-N coupling reactions.

A red-emissive two-photon fluorescent probe for mitochondrial sodium ions in live tissue

A cyclocyanine (CC)-based organic small molecule two-photon (TP) fluorescent probe (CCNa1) was developed for mitochondrial sodium ion sensing.CCNa1exhibits a low solvatochromic shift and strong TP fluorescence enhancement at 575 nm upon binding to Na

Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides

A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.

Iridium complex-linked porous organic polymers for recyclable, broad-scope photocatalysis of organic transformations

Two rigid porous organic polymers (Ir-POP-1 and Ir-POP-2) were prepared from the coupling reactions of tetraphenylmethane tetraborate and two [Ir(ppy)2(dtbbpy)]+-based bitopic linkers and applied as heterogeneous visible-light photocatalysts for organic transformations. Ir-POP-2 was found to exhibit high catalytic activity for a wide range of organic reactions, which include Smiles-Truce rearrangement of alkyliodides, desulfurative conjugate addition to Michael acceptors, and aerobic oxidations of sulfides and arylboronic acids. For all the transformations, Ir-POP-2 could achieve heterogeneous photocatalytic efficiency that rivals that of the homogeneous prototype iridium complexes. This remarkably high photocatalytic performance has been attributed to the large pore size of the conjugated backbone. The new heterogeneous photocatalyst was also highly stable to achieve good recyclability for all the studied reactions and could be reused eight to nineteen times.

Characteristic Hydrogen Bonding Observed in the Crystals of Aromatic Sulfonamides: 1D Chain Assembly of Molecules and Chiral Discrimination on Crystallization

N-Phenylbenzenesulfonamides exist preferentially in (+)- or (-)-synclinal conformations, which place the aromatic rings at both ends in the same direction with a twist. We have systematically analyzed the crystal structure of secondary aromatic sulfonamides bearing methyl, ethyl, and/or methoxy groups on the benzene rings. Intermolecular hydrogen bonding between the sulfonamide protons and sulfonyl oxygens was observed in 81 out of 85 crystals. The intermolecular hydrogen-bonding patterns could be classified into four types, i.e. Dimeric, Zigzag, Helical, and Straight patterns, with retention of the synclinal conformation of the sulfonamide moiety. We investigated the relationship between the hydrogen-bonding pattern and the proportion of the compounds that show chiral crystallization. On the basis of our classification of the intermolecular hydrogen bonds of aromatic sulfonamides, the crystals with Dimeric and Zigzag patterns, which both have enantiomeric synclinal conformers, intrinsically become achiral, except for kryptoracemates. In contrast, a high proportion of compounds with Helical or Straight patterns in the crystals showed chiral crystallization. Our classification is useful for discussion regarding the chirality of molecular assemblies, on the basis of the conformational chirality of the molecules in the crystal.

Visible Light Mediated Aryl Migration by Homolytic C?N Cleavage of Aryl Amines

The photocatalytic preparation of aminoalkylated heteroarenes from haloalkylamides via a 1,4-aryl migration from nitrogen to carbon, conceptually analogous to a radical Smiles rearrangement, is reported. This method enables the substitution of amino group

Synthesis of N -Arylsulfonamides by a Copper-Catalyzed Reaction of Chloramine-T and Arylboronic Acids at Room Temperature

A copper-catalyzed Chan-Lam-coupling-like reaction of a (het)arylboronic acid and chloramine-T (or a related compound) has been developed for the synthesis of N -arylsulfonamides at room temperature in moderate to good yields, with good tolerance of functional groups. In this process, it is believed that chloramine-T serves as an electrophile.

CuI catalyzed sulfamidation of arylboronic acid using TsNBr2 at room temperature

An expeditious protocol for amidation arylboronic acid has been developed using TsNBr2 as the nitrogen source in presence of a CuI as catalyst. Various arylboronic acids could be transformed into corresponding N-arylsulfonamide derivatives within a very short time using CuI as catalyst in presence of DBU at room temperature.

Sustainable synthesis of sulfonamides using supported ionic liquid phase catalyst containing Keggin-type anion

A silica-supported ionic liquid phase catalyst containing Keggin-type anion has been prepared by covalent grafting of ferrocene-tagged ionic liquid in a matrix of silica followed by anion metathesis reaction. This novel catalyst served as a robust heterogeneous catalyst for the synthesis of biologically active sulfonamides from 4-toluenesulfonyl chloride and amines. Additionally, recycling experiments showed that the catalyst could be reused five times.

Discovery, Optimization, and Biological Evaluation of Sulfonamidoacetamides as an Inducer of Axon Regeneration

Axon regeneration after injury in the central nervous system is hampered in part because if an age-dependent decline in the intrinsic axon growth potential, and one of the strategies to stimulate axon growth in injured neurons involves pharmacological manipulation of implicated signaling pathways. Here we report phenotypic cell-based screen of chemical libraries and structure-activity-guided optimization that resulted in the identification of compound 7p which promotes neurite outgrowth of cultured primary neurons derived from the hippocampus, cerebral cortex, and retina. In an animal model of optic nerve injury, compound 7p was shown to induce growth of GAP-43 positive axons, indicating that the in vitro neurite outgrowth activity of compound 7p translates into stimulation of axon regeneration in vivo. Further optimization of compound 7p and elucidation of the mechanisms by which it elicits axon regeneration in vivo will provide a rational basis for future efforts to enhance treatment strategies.