77925-80-5

Usage

Uses

Used in Organic Synthesis:
N-(Benzyloxy)-2-nitrobenzenesulfonamide is used as a building block in organic synthesis for the creation of biologically active molecules and pharmaceuticals. Its unique structure allows for versatile chemical reactions, making it a valuable component in the development of new compounds with potential therapeutic applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, N-(Benzyloxy)-2-nitrobenzenesulfonamide is used for its inhibitory activity against certain enzymes. This property suggests its potential use in the development of drugs targeting specific enzymatic pathways, which could be beneficial in treating various diseases and conditions.
Used in Research and Development:
Due to its unique chemical structure and properties, N-(Benzyloxy)-2-nitrobenzenesulfonamide is used in research and development across various fields of chemistry and pharmacology. It serves as a subject of study for understanding its reactivity, stability, and potential interactions with biological systems, which can contribute to the advancement of scientific knowledge and the discovery of new applications.

Upstream product

• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 622-33-3 N-benzyloxyamine 

Downstream Products

• 939387-56-1 diethyl 3-[N-benzyloxy-N-(2-nitrobenzenesulfonyl)amino]prop-1-ynylphosphonate 
• 939387-92-5 diethyl (Z)-3-[N-benzyloxy-N-(2-nitrobenzenesulfonyl)amino]-1-(thien-2-yl)prop-1-enylphosphonate 
• 939387-88-9 diethyl (Z)-3-[N-acetyl-N-(benzyloxy)amino]-1-(4-nitrophenyl)prop-1-enylphosphonate 
• 939387-94-7 diethyl (Z)-3-[N-acetyl-N-(benzyloxy)amino]-1-(thien-2-yl)prop-1-enylphosphonate 
• 939387-98-1 diethyl 3-[N-acetyl-N-(benzyloxy)amino]-1-(thien-2-yl)propylphosphonate 
• 939387-86-7 diethyl 3-[N-benzyloxy-N-(2-nitrobenzenesulfonyl)amino]-1-(4-nitrophenyl)prop-1-enylphosphonate 
• 1048037-17-7 C₂₃H₁₉N₃O₇S 
• 1463501-45-2 (2S,5R)-1-tert-butyl 2-ethyl 5-(N-(benzyloxy)-(2-nitrophenyl)sulfonamido)piperidine-1,2-dicarboxylate 
• 1471297-48-9 (3R,6S)-6-(1,2,4-oxadiazol-3-yl)piperidin-3-yl(benzyloxy)carbamic chloride 
• 1471297-50-3 (2S,5R)-6-(benzyloxy)-2-(1,2,4-oxadiazol-3-yl)-1,6-diazabicyclo[3.2.1]octan-7-one 
• 1471297-60-5 (2S,5R)-2-(5-amino-1,2,4-oxadiazol-3-yl)-6-(benzyloxy)-1,6-diazabicyclo[3.2.1]octan-7-one 
• 1416134-63-8 (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid ethyl ester 
• 1471297-71-8 (2S,5R)-tert-butyl 2-(5-(1-(((9H-fluoren-9-yl)methoxy)carbonyl)piperidin-4-yl)-1,2,4-oxadiazol-3-yl)-5-(benzyloxyamino)piperidine-1-carboxylate 
• 1471297-75-2 (9H-fluoren-9-yl)methyl 4-(3-((2S,5R)-5-(benzyloxy(chlorocarbonyl)amino)piperidin-2-yl)-1,2,4-oxadiazol-5-yl)piperidine-1-carboxylate 

Relevant academic research and scientific papers

Endo-Hydroxamic Acid Monomers for the Assembly of a Suite of Non-native Dimeric Macrocyclic Siderophores Using Metal-Templated Synthesis

An expedited synthesis of endo-hydroxamic acid aminocarboxylic acid (endo-HXA) compounds has been developed. These monomeric ligands are relevant to the synthesis of metal-macrocycle complexes using metal-templated synthesis (MTS), and the downstream production of apomacrocycles. Macrocycles can display useful drug properties and be used as ligands for radiometals in medical imaging applications, which supports methodological advances in accessing this class of molecule. Six endo-HXA ligands were prepared that contained methylene groups, ether atoms, or thioether atoms in different regions of the monomer (1-6). MTS using a 1:2 Fe(III)/ligand ratio furnished six dimeric hydroxamic acid macrocycles complexed with Fe(III) (1a-6a). The corresponding apomacrocycles (1b-6b) were produced upon treatment with diethylenetriaminepentaacetic acid (DTPA). Constitutional isomers of the apomacrocycles that contained one ether oxygen atom in the diamine-containing (2b) or dicarboxylic acid-containing (3b) region were well resolved by reverse-phase high-performance liquid chromatography (RP-HPLC). Density functional theory calculations were used to compute the structures and solvated molecular properties of 1b-6b and showed that the orientation of the amide bonds relative to the pseudo-C2 axis was close to parallel in 1b, 2b, and 4b-6b but tended toward perpendicular in 3b. This conformational constraint in 3b reduced the polarity compared with 2b, consistent with the experimental trend in polarity observed using RP-HPLC. The improved synthesis of endo-HXA ligands allows expanded structural diversity in MTS-derived macrocycles and the ability to modulate macrocycle properties.

Synthesis of Avibactam Derivatives and Activity on β-Lactamases and Peptidoglycan Biosynthesis Enzymes of Mycobacteria

There is a renewed interest for β-lactams for treating infections due to Mycobacterium tuberculosis and M. abscessus because their β-lactamases are inhibited by classical (clavulanate) or new generation (avibactam) inhibitors, respectively. Here, access to an azido derivative of the diazabicyclooctane (DBO) scaffold of avibactam for functionalization by the Huisgen–Sharpless cycloaddition reaction is reported. The amoxicillin–DBO combinations were active, indicating that the triazole ring is compatible with drug penetration (minimal inhibitory concentration of 16 μg mL?1 for both species). Mechanistically, β-lactamase inhibition was not sufficient to account for the potentiation of amoxicillin by DBOs. Thus, the latter compounds were investigated as inhibitors of l,d-transpeptidases (Ldts), which are the main peptidoglycan polymerases in mycobacteria. The DBOs acted as slow-binding inhibitors of Ldts by S-carbamoylation indicating that optimization of DBOs for Ldt inhibition is an attractive strategy to obtain drugs selectively active on mycobacteria.

Total Synthesis and Antimicrobial Activity of Chlorocatechelin A

Chlorocatechelin A (1) is a structurally unique microbial siderophore containing two units of 4-chloro-2,3-dihydroxybenzoic acid (CDB) and a characteristic acylguanidine structure. Purification from the microbe culture is not an easy task due to the labil

CRYSTALLINE FORM OF A BETA-LACTAMASE INHIBITOR

This disclosure provides compositions containing solid forms of sodium (2S,5R)-2-(1,3,4-oxadiazol-2-yl)-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl sulfate, and methods of manufacturing and using these compositions.

1,2,4-OXADIAZOLE AND 1,2,4-THIADIAZOLE BETA-LACTAMASE INHIBITORS

β-Lactamase inhibitor compounds (BLIs) are disclosed, including compounds that have activity against class A, class C or class D β-lactamases. Methods of manufacturing the BLIs, and uses of the compounds in the preparation of pharmaceutical compositions and antibacterial applications are also disclosed.

BETA-LACTAMASE INHIBITORS

Aryl substituted diazabicyclooctanes (DBO) compounds that inhibit β-lactamases of class A, class C or class D and potentiate β-lactam antibiotics are disclosed. In particular, this disclosure provides DBO compounds that, when used in the disclosed Synergy MIC Assay with a β-lactam antibiotic at a fixed concentration have an MIC of 8 μg/mL or less against one or more isogenic β-lactamase expressing bacterial strains.

ISOXAZOLE β-LACTAMASE INHIBITORS

β-Lactamase inhibitor compounds (BLIs) are disclosed, including compounds that have activity against class A, class C or class D β-lactamases. Methods of manufacturing the BLIs, and uses of the compounds in the preparation of pharmaceutical compositions and antibacterial applications are also disclosed.

1,3,4-OXADIAZOLE AND 1,3,4-THIADIAZOLE BETA-LACTAMASE INHIBITORS

β-Lactamase inhibitor compounds (BLIs) are disclosed, including compounds that have activity against class A, class C or class D β-lactamases. Methods of manufacturing the BLIs, and uses of the compounds in the preparation of pharmaceutical compositions and antibacterial applications are also disclosed.

Efficient one-pot synthesis of 1-alkoxy-2-arylaminoimidazolines from N-alkoxy-N-(2-aminoethyl)-2-nitrobenzenesulfonamides and arylisothiocyanates

A new synthetic approach towards 1-alkoxy-2-aminoimidazolines that uses N-alkoxy-N-(2-aminoethyl)-2-nitrobenzenesulfonamides as nucleophile reagents for the reaction with isothiocyanates is reported. Hence, the synthesis of 1-alkoxy-2-aminoimidazolines was performed in high yield with a one-pot procedure involving thiourea formation, nosyl group removal and spontaneous cyclization (42-77% overall yield).

O-Protected N-(2-Nitrophenylsulfonyl)hydroxylamines: Novel Reagents for the Synthesis of Hydroxamates

Preparative methods for novel O-protected N-(2-nitrophenylsulfonyl)hydroxylamines (8a-e) are described. Their versatility as intermediates en route to polyhydroxamates is examplified by the synthesis of a non-amide DFO analog 22.