42060-32-2

Usage

Uses

Used in Pharmaceutical Research:
N-benzyl-2-nitrobenzenesulfonamide is utilized as a reagent in organic synthesis and pharmaceutical research for its potential as an antitumor and antiparasitic agent. Its unique structure and reactivity contribute to the development of new drugs and therapies.
Used in Organic Synthesis:
As a building block in organic synthesis, N-benzyl-2-nitrobenzenesulfonamide is employed to create a variety of biologically active compounds, which can be further used in medicinal chemistry and drug discovery.
Used in Enzyme Inhibition and Protein Binding Studies:
N-benzyl-2-nitrobenzenesulfonamide serves as a research tool in the study of enzyme inhibition and protein binding, aiding scientists in understanding the mechanisms of action and potential applications in therapeutic interventions.

Upstream product

• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 100-46-9 benzylamine 
• 5455-59-4 2-Nitrobenzenesulfonamide 
• 100-51-6 benzyl alcohol 
• 245364-47-0 N-Boc-N-benzyl-o-nitrobenzenesulfonamide 
• 141381-72-8 1H-benzo[d][1,2,3]triazol-1-yl 2-nitrobenzenesulfonate 
• 62-53-3 aniline 
• 103-82-2 phenylacetic acid 
• 1441409-96-6 (E)-ethyl 2-cyano-2-(2-nitrophenylsulfonyloxyimino)acetate 
• 198572-71-3 N-(tert-butoxycarbonyl)-2-nitrobenzenesulfonamide 

Downstream Products

• 42060-39-9 N-methyl-N-benzyl-o-nitrobenzenesulfonamide 
• 100-46-9 benzylamine 
• 235089-83-5 N-benzyl-2-nitro-N-(1-phenethyl-allyl)-benzenesulfonamide 
• 42060-55-9 N-benzyl-N-methylbenzenesulfonamide 
• 21639-17-8 2-amino-N-benzyl-N-methyl-benzenesulfonamide 
• 1070655-59-2 7-ethyl-1-[2-(4-fluorophenyl)ethyl]-4-benzyl-1,4-diazaperhydroepin-2-one 
• 46922-55-8 (R)-N-benzyl-1-phenoxypropan-2-amine 
• 16053-59-1 C₁₈H₂₂ClNO*ClH 
• 34238-86-3 C₁₈H₂₃NO₂ 
• 483341-81-7 (1R,4R,6S)-4,6-bis[(N-benzyl)-o-nitrobenzenesulfon-amino]-cyclohex-2-enol 
• 483341-86-2 (1S,4S,6R)-4,6-bis[(N-benzyl)-o-nitrobenzenesulfon-amino]-cyclohex-2-enol 

Relevant academic research and scientific papers

One-pot synthesis ofN-substituted benzannulated triazolesviastable arene diazonium salts

A mild and effective one-pot synthesis of 1,2,3-benzotriazin-4(3H)-ones and benzothiatriazine-1,1(2H)-dioxide analogues has been developed. The method involves the diazotisation and subsequent cyclisation of 2-aminobenzamides and 2-aminobenzenesulfonamidesviastable diazonium salts, prepared using a polymer-supported nitrite reagent andp-tosic acid. The transformation was compatible with a wide range of aryl functional groups and amide/sulfonamide-substituents and was used for the synthesis of pharmaceutically important targets. The synthetic utility of the one-pot diazotisaton-cyclisation process was further demonstrated with the preparation of an α-amino acid containing 1,2,3-benzotriazin-4(3H)-one.

Chemoselective Hydrogenation of Nitroarenes Using an Air-Stable Base-Metal Catalyst

The reduction of nitroarenes to anilines as well as azobenzenes to hydrazobenzenes using a single base-metal catalyst is reported. The hydrogenation reactions are performed with an air-and moisture-stable manganese catalyst and proceed under relatively mild reaction conditions. The transformation tolerates a broad range of functional groups, affording aniline derivatives and hydrazobenzenes in high yields. Mechanistic studies suggest that the reaction proceeds via a bifunctional activation involving metal-ligand cooperative catalysis.

Direct Synthesis of Allyl Amines with 2-Nitrosulfonamide Derivatives via the Tsuji-Trost Reaction

The Tsuji-Trost Reaction is a palladium-catalysed allylation of nucleophiles that consists in the reaction of a nitrogen, carbon or oxygen-based nucleophiles with an allylic substrate bearing a leaving group. Here we present the use of 2-nitrosulfonamide derivatives as nucleophile, which are reactive under mild conditions. 2-nitrosulfonyl groups are well-known dual protective activator groups easy to introduce in any type of amine substrates. The resulting 2-nitrosulfonamide derivatives are ideal substrates for the Tsuji-Trost reaction to afford a convenient and flexible access to primary and dissymmetric secondary allyl amines. The optimised procedure is flexible (for solvent, temperature, functional groups) and has been applied with good to excellent yield to access to a wide range of allyl amine derivatives.

Metal-free synthesis of activated ynesulfonamides and tertiary enesulfonamides

An operationally simple synthesis of activated ynesulfonamides and enesulfonamides is described. Ynesulfonamides can be obtained through reaction of sulfonylamides with activated bromoalkynes and Triton B in a short time at room temperature. Likewise, terminal alkynes react with sulfonylamides to provide enesulfonamides. Z/E enesulfonamides can be transformed exclusively into E enesulfonamides.

COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND USE THEREOF AS INHIBITORS OF RAN GTPASE

Compounds of general formula IA, IB and IC outlined below, including pharmaceutically acceptable salts, solvates and hydrates thereof. Such compounds and pharmaceutical compositions comprising them may be used in medical conditions involving Ran GTPase.

Metal Free Bi(hetero)aryl Synthesis: A Benzyne Truce-Smiles Rearrangement

A new benzyne transformation is described that affords versatile biaryl structures without recourse to transition-metal catalysis or stoichiometric amounts of organometallic building blocks. Aryl sulfonamides add to benzyne upon fluoride activation, and then undergo an aryl Truce-Smiles rearrangement to afford biaryls with sulfur dioxide extrusion. The reaction proceeds under simple reaction conditions and has excellent scope for the synthesis of sterically hindered atropisomeric biaryl amines. All smiles: Metal-free biaryl synthesis is achieved by adding benzyne to arylsulfonamides. A Smiles rearrangement enables C-C bond formation, thus accessing a variety of functionalized biaryls under mild reaction conditions.

Ethyl 2-cyano-2-(2-nitrobenzenesulfonyloxyimino)acetate (o -NosylOXY): A recyclable coupling reagent for racemization-free synthesis of peptide, amide, hydroxamate, and ester

Ubiquitousness of amide and ester functionality makes coupling reactions extremely important. Although numerous coupling reagents are available, methods of preparation of the common and efficient reagents are cumbersome. Those reagents generate a substantial amount of chemical waste and lack recyclability. Ethyl 2-cyano-2-(2-nitrobenzenesulfonyloxyimino)acetate (o-NosylOXY), the first member of a new generation of coupling reagents, produces byproducts that can be easily recovered and reused for the synthesis of the same reagent, making the method more environmentally friendly and cost-effective. The synthesis of amides, hydroxamates, peptides, and esters using this reagent is described. The synthesis of the difficult sequences, for example, the islet amyloid polypeptide (22-27) fragment (with a C-terminal Gly, H-Asn-Phe-Gly-Ala-Ile-Leu-Gly-NH 2) and acyl carrier protein (65-74) fragment (H-Val-Gln-Ala-Ala-Ile- Asp-Tyr-Ile-Asn-Gly-OH), following the solid-phase peptide synthesis (SPPS) protocol and Amyloid β (39-42) peptide (Boc-Val-Val-IIe-Ala-OMe), following solution-phase strategy is demonstrated. Remarkable improvement is noticed with respect to reaction time, yield, and retention of stereochemistry. A mechanistic investigation and recyclability are also described.

Functionalization of mesoporous carbon with superbasic MgO nanoparticles for the efficient synthesis of sulfinamides

Highly basic MgO nanoparticles with different sizes have been successfully immobilized over mesoporous carbon with different pore diameters by a simple wet-impregnation method. The prepared catalysts have been characterized by various sophisticated techniques, such as XRD, nitrogen adsorption, electron energy loss spectroscopy, high-resolution TEM, X-ray photoelectron spectroscopy, and the temperature-programmed desorption of CO2. XRD results reveal that the mesostructure of the support is retained even after the huge loading of MgO nanoparticles inside the mesochannels of the support. It is also demonstrated that the particle size and dispersion of the MgO nanoparticles on the support can be finely controlled by the simple adjustment of the textural parameters of the supports. Among the support materials studied, mesoporous carbon with the largest pore diameter and large pore volume offered highly crystalline small-size cubic-phase MgO nanoparticles with a high dispersion. The basicity of the MgO-supported mesoporous carbons can also be controlled by simply changing the loading of the MgO and the pore diameter of the support. These materials have been employed as heterogeneous catalysts for the first time in the selective synthesis of sulfinamides. Among the catalysts investigated, the support with the large pore diameter and high loading of MgO showed the highest activity with an excellent yield of sulfinamides. The catalyst also showed much higher activity than the pristine MgO nanoparticles. The effects of the reaction parameters, including the solvents and reaction temperature, and textural parameters of the supports in the activity of the catalyst have also been demonstrated. Most importantly, the catalyst was found to be highly stable, showing excellent activity even after the third cycle of reaction. Reuse and recycle: Highly basic MgO-functionalized mesoporous carbon with different pore diameters has been prepared (see picture). The material showed a much higher performance in the synthesis of sulfinamides than pure MgO nanoparticles. The catalyst was also highly stable and could be reused several times without affecting its activity. Copyright

A facile enantioselective synthesis of enantiomerically pure (R)-phenoxybenzamine hydrochloride using the hydrolytic kinetic resolution method

A practical and highly efficient enantioselective synthesis of (R)-phenoxybenzamine hydrochloride has been described for the first time using Jacobsen's hydrolytic kinetic resolution of a terminal epoxide as a key step and source of chirality.