25798-61-2

Usage

Uses

Used in Organic Synthesis:
Ethanone, 1-(2-nitrosophenyl)(9CI) is utilized as a reagent in organic synthesis for its ability to participate in various chemical reactions, contributing to the formation of new compounds and structures.
Used in Analytical Chemistry:
In the field of analytical chemistry, Ethanone, 1-(2-nitrosophenyl)(9CI) serves as a chelating agent, which is instrumental in the detection, measurement, and analysis of metal ions in complex samples.
Used in Pharmaceutical Research:
Ethanone, 1-(2-nitrosophenyl)(9CI) is used as a subject of study in pharmaceutical research due to its observed anti-inflammatory and antiproliferative properties, which may lead to the development of new therapeutic agents.
Used in Medicinal Chemistry:
Ethanone, 1-(2-nitrosophenyl)(9CI) is also employed in medicinal chemistry for its potential to be further explored and optimized for use in the treatment of various conditions, given its demonstrated biological activities.

InChI:InChI=1/C8H7NO2/c1-6(10)7-4-2-3-5-8(7)9-11/h2-5H,1H3

Upstream product

• 133795-10-5 N-<<(2-nitrophenyl)-1-methylmethoxy>carbonyl>cyclohexylamine 
• 207516-11-8 Phosphoric acid (E)-(2S,3R)-2-amino-3-hydroxy-octadec-4-enyl ester bis-[1-(2-nitro-phenyl)-ethyl] ester 
• 114119-94-7 1-(2-nitrophenyl)diazoethane 
• 220863-62-7 abscisic acid 1-(2-nitrophenyl)ethyl ester 
• 67030-27-7 adenosine 5'-triphosphate γ(1-[2-nitrophenyl]ethyl) ester 
• 65783-00-8 2-(2-nitrophenyl)propanenitrile 
• 116271-34-2 hydrazone of 2-nitroacetophenone 
• 577-59-3 2-acetylnitrobenzene 
• 207516-14-1 bis-[1-(2-nitrophenyl)ethyl]-N,N-diisopropylphosphoramidite 
• 80379-10-8 1-(2-nitrophenyl)ethan-1-ol 
• 32313-86-3 acetic acid 1-(2-nitro-phenyl)-ethyl ester 

Relevant academic research and scientific papers

Photochemical release of ATP from "caged ATP" studied by time-resolved infrared spectroscopy

Rapid scan Fourier transform infrared (FTIR) spectroscopy and time-resolved single wavelength infrared (IR) spectroscopy have been used to follow the photochemical release of adenosine 5′-triphosphate (ATP) from P3-(1-(2-nitrophenyl)ethyl) adenosine 5′-triphosphate (caged ATP). Vibrational difference spectra for the formation first of the aci-nitro anion intermediate and subsequently of ATP and the byproduct(s) were obtained by rapid scan FTIR spectroscopy in the millisecond-to-second time domain. Vibrational modes of the phosphate groups of ATP and caged ATP in the range 1250-900 cm-1 could be assigned on the basis of triple and single 18O labeling in caged ATP at the terminal phosphate group and at the bridging oxygen between the terminal phosphate and the 1-(2-nitrophenyl)ethyl group, respectively. The rapid formation and subsequent decay of the aci-nitro anion intermediate were monitored by single-wavelength time-resolved IR spectroscopy at 1251 cm-1 (predominantly a PO2- mode of caged ATP and the aci-nitro intermediate). The appearance of the free γ-phosphate group of ATP was monitored at 1119 cm-1 (POs2- mode of ATP). Decay of the aci-nitro anion intermediate and formation of ATP were well fitted by single exponentials to give a mean rate constant of 218 ± 33 s-1 at pH 7 and 22 °C.

Photolytic cleavage of 1-(2-nitrophenyl)ethyl ethers involves two parallel pathways and product release is rate-limited by decomposition of a common hemiacetal intermediate

Time-resolved FTIR spectroscopic studies of the flash photolysis of several 1-(2-nitrophenyl)-ethyl ethers derived from aliphatic alcohols showed that a long-lived hemiacetal intermediate was formed during the reaction. Breakdown of this intermediate was

Photochemical Reaction Mechanisms of 2-Nitrobenzyl Compounds: Methyl Ethers and Caged ATP

The mechanism of methanol photorelease from 2-nitrobenzyl methyl ether (1) and 1-(2-nitrophenyl)ethyl methyl ether (2), and of ATP release from adenosine-5′-triphosphate-[P3-(1-(2-nitrophenyl)-ethyl)] ester ('caged ATP', 3) was studied in various solvents by laser flash photolysis with UV-vis and IR detection. In addition to the well-known primary aci-nitro transients (A, λmax ≈ 400 nm), two further intermediates preceding the release of methanol, namely the corresponding 1,3-dihydrobenz[c]isoxazol-1-ol derivatives (B) and 2-nitrosobenzyl hemiacetals (C), were identified. The dependencies of the reaction rates of A-C on pH and buffer concentrations in aqueous solution were studied in detail. Substantial revision of previously proposed reaction mechanisms for substrate release from 2-nitrobenzyl protecting groups is required: (a) A novel reaction pathway of the aci-tautomers A prevailing in buffered aqueous solutions, e.g., phosphate buffer with pH 7, was found. (b) The cyclic intermediates B were identified for the first time as the products formed by the decay of the aci-tautomers A in solution. A recently proposed reaction pathway bypassing intermediates B (Corrie et al. J. Am. Chem. Soc., 2003, 125, 8546-8554) is shown not to be operative. (c) Hemiacetals C limit the release rate of both 1 (pH 8) and 2 (pH 10). This observation is in contrast to a recent claim for related 2-nitrobenzyl methyl ethers (Corrie et al.). Our findings are important for potential applications of the 2-nitrobenzyl protecting group in the determination of physiological response times to bioagents ('caged compounds').

A caged cyanide

A photoactivatable caged cyanide, 1-(2-nitrophenyl)ethyl (NPE) cyanide, was synthesized, which upon irradiation in the near UV releases cyanide. It is demonstrated that the compound can be used to induce formation of the Fe III-CN- complex in the heme protein nitrophorin 4 from Rhodnius prolixus.

Supramolecular photochemistry of encapsulated caged: Ortho -nitrobenzyl triggers

ortho-Nitrobenzyl (oNB) triggers have been extensively used to release various molecules of interest. However, the toxicity and reactivity of the spent chromophore, o-nitrosobenzaldehyde, remains an unaddressed difficulty. In this study we have applied the well-established supramolecular photochemical concepts to retain the spent trigger o-nitrosobenzaldehyde within the organic capsule after release of water-soluble acids and alcohols. The sequestering power of organic capsules for spent chromophores during photorelease from ortho-nitrobenzyl esters, ethers and alcohols is demonstrated with several examples.

A view on phosphate ester photochemistry by time-resolved solid state NMR. Intramolecular redox reaction of caged ATP

The light-driven intramolecular redox reaction of adenosine-5′- triphosphate-[P3-(1-(2-nitrophenyl)-ethyl)]ester (caged ATP) has been studied in frozen aqueous solution using time-resolved solid state NMR spectroscopy under continuous illumination conditions. Cleavage of the phosphate ester bond leads to 0.3, 1.36, and 6.06 ppm downfield shifts of the α-, β-, and γ-phosphorus resonances of caged ATP, respectively. The observed rate of ATP formation is 2.4 ± 0.2 h-1 at 245 K. The proton released in the reaction binds to the triphosphate moiety of the nascent ATP, causing the upfield shifts of the 31P resonances. Analyses of the reaction kinetics indicate that bond cleavage and proton release are two sequential processes in the solid state, suggesting that the 1-hydroxy,1-(2-nitrosophenyl)-ethyl carbocation intermediate is involved in the reaction. The β-phosphate oxygen atom of ATP is protonated first, indicating its proximity to the reaction center, possibly within hydrogen bonding distance. The residual linewidth kinetics are interpreted in terms of chemical exchange processes, hydrogen bonding of the β-phosphate oxygen atom and evolution of the hydrolytic equilibrium at the triphosphate moiety of the nascent ATP. Photoreaction of caged ATP in situ gives an opportunity to study structural kinetics and catalysis of ATP-dependent enzymes by NMR spectroscopy in rotating solids. the Owner Societies.

Photocleavage of o-nitrobenzyl ether derivatives for rapid biomedical release applications

The externally controlled cleavage of covalently linked prodrugs, proteins, or solid-phase formulation vehicles offers potential advantages for controlled drug or gene delivery. A series of o-nitrobenzyl ester compounds (1-8) were synthesized to allow a systematic study of photolability. The o-nitrobenzyl ester was strictly required for photolability, while imido esters were not photolabile. The degradation kinetics of 1-o-phenylethyl ester was an order of magnitude faster than that of o-nitrobenzyl ester. Tosylate, phosphate, and benzoate derivatives of 1-o-nitrophenylethyl displayed similar photolability (>80% decomposition within 10 min at 3.5 mW/cm2 at 365 nm). O-o-Nitrobenzyl O′,O″-diethyl phosphate displayed the fastest decomposition at photoirradiation condition (3.5 mW/cm2, 365 nm) suitable for biological systems. We report the synthesis and photo-decomposition of 1-o-nitrophenylethyl derivatives amenable for the creation of photolabile prodrugs or formulation particles for drug depots, DNA condensation, or tissue engineering applications.

Novel photoacid generators for photodirected oligonucleotide synthesis

Photodirected oligonucleotide synthesis uses either direct or indirect light-dependent 5′-deprotection. Both have been reported to give lower stepwise synthetic yields than conventional methods. The deficiency appears to be due to incomplete deprotection at the oligonucleotide 5′-position and, additionally in the case where photodirection is indirect and uses photogenerated photoacid to effect 5′-detritylation, the depurinating effects of strong acid. We have developed novel photosensitive-2-nitrobenzyl esters that on irradiation with near UV light generate α-chloro-substituted acetic acids, such as trichloroacetic acid, which are widely and successfully used in conventional solid-phase oligonucleotide synthesis. α-Phenyl-4,5-dimethoxy-2-nitrobenzyltrichloroacetate and α-phenyl-4,5-dimethoxy-2,6-dinitrobenzyltrichloroacetate showed appropriate photochemical characteristics and were used for photodirected synthesis of a variety of oligonucleotides, including (T)5, TATAT, TGTGT, (T)10, (AT)5, (CT)5 (GT)5 and (TGCAT)2 on a modified Millipore Expedite DNA synthesizer. The outcomes were compared with those obtained by use of directly added trichloroacetic acid (conventional synthesis). The stepwise yields for the two methods were essentially identical.

Photoactive materials applicable to imaging systems

Organic photoprecursors of amines are provided for use in photosensitive imaging systems, finding particular application in the preparation of lithographic printing plates. Said photoprecursors generate free amines on exposure to long wavelength UV or visible radiation, have high solubility in organic solvents, and include photolabile 2-nitrobenzyl functional groups. Methods for the synthesis of the photoprecursors are described, and the use of the said photoprecursors for the production of printing plates using both positive working and negative working techniques are discussed.

Synthesis and evaluation of a photolyzable derivative of sphingosine 1-phosphate-caged SPP

The synthesis of a photolyzable sphingosine 1-phosphate derivative is reported via the reaction of N-(tert-butoxycarbonyl)-2-N,3-O-isopropylidenesphingosine 7 and bis(α-methyl-o-nitrobenzyl) N,N-diisopropylphosphoramidite. Stimulation of DNA synthesis upon illumination of caged SPP-loaded cells is also described.