5455-59-4

Usage

Uses

Used in Pharmaceutical Industry:
2-Nitrobenzenesulfonamide is used as a pharmaceutical agent for its carbonic anhydrase inhibitory properties. It plays a crucial role in the treatment of conditions that involve the regulation of acid-base balance in the body, such as glaucoma, certain types of epilepsy, and altitude sickness. By inhibiting carbonic anhydrase, it helps in reducing intraocular pressure and preventing the overproduction of carbon dioxide, which can lead to these medical conditions.
Used in Chemical Research:
In the field of chemical research, 2-Nitrobenzenesulfonamide serves as an important compound for studying the mechanisms of carbonic anhydrase enzymes and their role in various biological processes. Its use in research contributes to the development of new drugs and therapies targeting carbonic anhydrase-related diseases.
Used in Environmental Applications:
2-Nitrobenzenesulfonamide can also be utilized in environmental applications, such as water treatment and pollution control. Its ability to inhibit carbonic anhydrase can be leveraged to control the growth of certain microorganisms and algae that contribute to water pollution. This application helps in maintaining the ecological balance and ensuring the availability of clean water resources.

InChI:InChI=1/C6H6N2O4S/c7-13(11,12)6-4-2-1-3-5(6)8(9)10/h1-4H,(H2,7,11,12)

Upstream product

• 22057-44-9 1-(benzylsulfanyl)-2-nitrobenzene 
• 1155-00-6 bis(2-nitrophenyl)disulfide 
• 88-73-3 2-Chloronitrobenzene 
• 863033-39-0 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[1-(2-nitro-benzenesulfonyl)-6-oxo-1,6-dihydro-purin-9-yl]-tetrahydro-furan-3-yl ester 
• 62-53-3 aniline 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 

Downstream Products

• 100606-64-2 2-nitro-benzenesulfonic acid-(trichlorophosphoranyliden-amide) 
• 3306-62-5 2-AMINOBENZENESULFONAMIDE 
• 23530-44-1 N-((2-nitrophenyl)sulfonyl)acetamide 
• 101251-75-6 chloroacetyl-(2-nitro-benzenesulfonyl)-amine 
• 84274-65-7 N--2-nitrobenzolsulfonamid 
• 149552-41-0 2-nitro-N-(phenyl-λ³-iodaneylidene)benzenesulfonamide 
• 81792-98-5 N-Isobutyryl-2-nitro-benzenesulfonamide 
• 198572-71-3 N-(tert-butoxycarbonyl)-2-nitrobenzenesulfonamide 
• 107616-17-1 N,N-Diallyl-2-nitro-benzenesulfonamide 
• 211512-09-3 N,N-bis[[6-(hydroxymethyl)pyridin-2-yl]methyl]2-nitrobenzenesulfonamide 
• 307313-69-5 N-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-hydroxy-propyl]-2-nitro-benzenesulfonamide 
• 52187-72-1 N,N-dichloro-2-nitrobenzenesulfonamide 
• 634911-92-5 (11R)-11-dimethylcarbamoylmethyl-11-[1,3]dioxolan-2-yl-1,2-dimethoxy-7-(2-nitrobenzenesulfonyl)-6,7,8,9,10,11,12,13-octahydro-5H-7,14-diazacycloundeca[a]indene-14-carboxylic acid tert-butyl ester 
• 634911-97-0 3-(2-Acetoxy-ethyl)-2-[(Z)-(S)-3-dimethoxymethyl-3-ethoxycarbonylmethyl-6-(2-nitro-benzenesulfonylamino)-hex-1-enyl]-6,7-dimethoxy-indole-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Conformational properties of ortho-nitrobenzenesulfonamide in gas and crystalline phases. Intra- and intermolecular hydrogen bond

A combined gas-phase electron diffraction and quantum chemical (B3LYP/6-311+G, B3LYP/cc-pvtz, MP2/cc-pvtz) study of molecular structure of 2-nitrobenzenesulfonamide (2-NBSA) was carried out. Quantum chemical calculations showed that 2-NBSA has four confor

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.

MYELINATION STIMULATOR COMPOUNDS, AND METHODS OF TREATMENT

The invention is directed towards compounds, methods of stimulating myelination, stimulating proliferation of oligodendrocytes (OLs) or stimulating oligodendrocyte precursor cells and methods of treating diseases, disorders or symptoms thereof.

Rational Design, synthesis and biological evaluation of novel triazole derivatives as potent and selective PRMT5 inhibitors with antitumor activity

Protein arginine methyltransferase 5 (PRMT5) is responsible for the mono-methylation and symmetric dimethylation of arginine, and its expression level and methyl transferring activity have been demonstrated to have a close relationship with tumorigenesis, development and poor clinical outcomes of human cancers. Two PRMT5 small molecule inhibitors (GSK3326595 and JNJ-64619178) have been put forward into clinical trials. Here, we describe the design, synthesis and biological evaluation of a series of novel, potent and selective PRMT5 inhibitors with antiproliferative activity against Z-138 mantle cell lymphoma cell line. Among them, compound C_4 exhibited the highest potency with enzymatic and cellular level IC50 values of 0.72 and 2.6 μM, respectively, and displayed more than 270-fold selectivity toward PRMT5 over several other isoenzymes (PRMT1, PRMT4 and PRMT6). Besides, C_4 demonstrated obvious cell apoptotic effect while reduced the cellular symmetric arginine dimethylation levels of SmD3 protein. The potency, small size, and synthetic accessibility of this compound class provide promising hit scaffold for medicinal chemists to further explore this series of PRMT5 inhibitors.

Synthesis of (-)-Cytisine Using a 6- endo aza-Michael Addition

An asymmetric synthesis of (-)-cytisine has been achieved. The piperidine C-ring was formed using a stereodivergent intramolecular 6-endo aza-Michael addition. The B-ring was established by intramolecular pyridine N-alkylation. The absolute stereochemistry was established by an Evans acyl oxazolidinone enolate alkylation reaction that proceeded with an unexpected stereochemical outcome due to participation of the pyridine nitrogen lone pair.

1. 1 - dioxo - 4H - benzo [1, 2, 4] - thiadiazine hydrochloric acid salt compound and its preparation method

The invention discloses a 1,1-dioxo-4H-benzo[1,2,4]-thiadiazine hydrochloride compound and a preparation method thereof, belonging to the technical field of organic synthesis. The technical scheme has the key point as follows: the 1,1-dioxo-4H-benzo[1,2,4]- thiadiazine hydrochloride compound has the structure as shown in the specification, wherein R is H, -CH3 or -C2H5. The invention also discloses the preparation method of the 1,1-dioxo-4H-benzo[1,2,4]-thiadiazine hydrochloride compound. The preparation method is simple, convenient and easy to operate, relatively high in reaction efficiency and relatively good in repeatability, and raw materials are cheap and available.

Syntheses, biological activities and SAR studies of novel carboxamide compounds containing piperazine and arylsulfonyl moieties

A series of novel carboxamide compounds 19a-19j, 20a-20j and 22a-22d containing piperazine and arylsulfonyl moieties have been synthesized. The bioassay results showed that some compounds exhibited favorable herbicidal activities against dicotyledonous plants and many of them possessed excellent antifungal activities. Among 24 novel compounds, some showed superiority over the commercial fungicides Chlorothalonil, Dimethomorph, Thiophanate-methyl, Iprodione, and Zhongshengmycin at 500 mg/L concentration. Some compounds also exhibited high KARI inhibitory activity at 100 γ1/4g/mL concentration and could be used as new KARI lead inhibitors for further studies. Moreover, SAR of these new compounds were comprehensively investigated using different computational methods in which 3D-QSAR model obtained provided useful information for further structural optimization for the discovery of new fungicides. The results of this research will contribute to explore comprehensive biological activities of piperazine-containing compounds in different areas of chemistry.

Ruthenium trichloride catalyzed synthesis of 2,3-unsaturated-N-glycosides via Ferrier azaglycosylation

An efficient, economical and mild protocol for the synthesis of 2,3-unsaturated-N-glycosides has been developed using ruthenium(III) chloride. The Ferrier azaglycosylation of glycals with various N-nucleophiles such as sulfonamides, benzamides, carbamates and N-substituted sulfonamides proceeded smoothly to afford the corresponding 2,3-unsaturated-N-glycosides or ‘N-pseudoglycals’ in good yields (64–98%). High α-anomeric selectivity was observed with N-substituted sulfonamides such as N-benzyl or N-phenyl sulfonamides under similar conditions.

Integrated structure-based activity prediction model of benzothiadiazines on various genotypes of HCV NS5b polymerase (1a, 1b and 4) and its application in the discovery of new derivatives

This work presents the first structure-based activity prediction model for benzothiadiazines against various genotypes of HCV NS5b polymerase (1a, 1b and 4).The model is a comprehensive workflow of structure-based field template followed by guided docking. The field template was used as a pre-filter and a tool to provide hits in good orientation and position. It was created based on detailed molecular interaction field analysis which includes Topomer CoMFA, grid independent analysis and Superstar. On the other hand, Guided docking was used as a refinement and assessment tool. It was actively directed by two scores: Moldock score as an interaction descriptor (r2 = 0.65) and a template similarity score as a measure for accurate binding-mode compliance. The docking template was based on energy-based pharmacophore analysis. The whole procedure was formulated and tweaked for both screening (ROC of AUC = 0.91) and activity prediction (r2 of 0.8) for the genotype 1a. In order to widen the model scope, linear interaction energy was used as a tool for predicting activities of other genotypes based on the docked ligand poses while mutation binding energy was used to investigate the effect of each amino acid mutation in genotype 4. The model was applied for structure-based fragment hopping by screening a library designed by reaction enumeration. A top scoring hit was used to generate a focused library such that it has lower TPSA than the original class ligands and thus better pharmacokinetic properties. After that, experimental validation was carried out by the synthesis of this library and its biological evaluation which yielded compounds that exhibit EC50 ranging from 1.86 to 23 μM.