4974-57-6

Usage

Uses

Used in Chemical Industry:
P-NITROPHENYLGLYOXAL is used as a solvent for various chemical reactions, facilitating the process and improving the efficiency of the reactions. Its solubility and reactivity make it a preferred choice in the chemical industry.
Used in Pharmaceutical Industry:
P-NITROPHENYLGLYOXAL is used as a key compound in the development of new drugs. Its ability to form complexes with other molecules allows for the creation of novel drug candidates with potential therapeutic applications.
Used in Analytical Chemistry:
P-NITROPHENYLGLYOXAL is used as a reagent in the assay of enzymes such as arginase. Its unique chemical properties enable the accurate measurement of enzyme activity, contributing to the advancement of research in biochemistry and molecular biology.

InChI:InChI=1/C8H5NO4/c10-5-8(11)6-1-3-7(4-2-6)9(12)13/h1-5H

Upstream product

• 100-19-6 (4-nitrophenyl)ethanone 
• 1439-43-6 1-(4-nitro-phenyl)-2-(triphenyl-λ⁵-phosphanylidene)-ethanone 
• 91736-70-8 3-(4-nitrophenyl)-1-benzyl-2-propoxy-1,2-dihydroquinoxaline 
• 937-31-5 (4-Nitrophenyl)acetylene 
• 100-13-0 4-nitrostyrene 
• 4996-22-9 4-nitrophenylglyoxal 
• 110944-98-4 2-iodo-1-(4-nitrophenyl)ethanone 
• 1044637-41-3 N-(2-oxo-2-(p-nitrophenyl)ethoxy)phthalimide 
• 18731-47-0 1-(4-nitrophenyl)-2-nitroethanol 
• 75295-87-3 (4-nitro-phenyl)-glyoxal-2-(triphenylphosphoranylidene-hydrazone) 
• 91736-68-4 3-(4-nitrophenyl)-2-propoxy-1-(4-nitrophenylmethyl)-1,2-dihydroquinoxaline 
• 99-81-0 4-Nitrophenacyl bromide 

Downstream Products

• 118693-61-1 (S)-2-Amino-4-{(R)-1-(carboxymethyl-carbamoyl)-2-[1-hydroxy-2-(4-nitro-phenyl)-2-oxo-ethylsulfanyl]-ethylcarbamoyl}-butyric acid 
• 111336-69-7 5-(4-nitrophenyl)-1,2,4-triazine 
• 140473-02-5 (4-Nitro-phenyl)-(2-phenyl-1,9b-dihydro-5-oxa-3,3a-diaza-cyclopenta[a]naphthalen-4-yl)-methanone 
• 76809-52-4 6-(4-Nitro-phenyl)-4-oxy-1H-pyrazin-2-one 
• 128960-38-3 1-(N-p-nitrophenacylidene)amino-4-phenyl-1,2,3-triazole 
• 2187-25-9 N-(α-hydroxy-4-nitro-phenacyl)-acetamide 
• 1948-96-5 1-Nitro-4-(α-hydroxy-α-phenylacetamino-acetyl)-benzol 
• 121247-14-1 2-(4'-aminophenyl)-6-chloro-3-methoxyimidazo<1,2-b>pyridazine 
• 121247-12-9 6-chloro-3-methoxy-2-(4'-nitrophenyl)imidazo<1,2-b>pyridazine 
• 128863-62-7 2-(4'-aminophenyl)-6-(2-ethoxyphenoxy)-3-methoxyimidazo<1,2-b>pyridazine 
• 128863-60-5 6-(2'-ethoxyphenoxy)-3-methoxy-2-(4-nitrophenyl)imidazo<1,2-b>pyridazine 
• 169120-41-6 6,7-dimethyl-2-(4-nitrophenyl)quinoxaline 
• 1063626-99-2 1,3-dimethyl-5-(2-(4-nitrophenyl)-2-oxoethylidene)-pyrimidine-2,4,6-trione 
• 131504-53-5 ethyl (E)-4-(4-nitrophenyl)-4-oxo-2-butenoate 

Relevant academic research and scientific papers

A novel class for carbonic anhydrases inhibitors and evaluation of their non-zinc binding

In this study, 23 different imidazole derivatives were synthesized, and the inhibitory properties of these derivatives against carbonic anhydrase I and II isoenzymes were investigated for the first time. The inhibition concentrations of the imidazole derivatives were found to be in the range of 2.89–115.5 nM. Docking studies examined the binding properties of the imidazole derivatives, and the structure–activity relationship is discussed. Theoretical calculations showed that the binding mode of the imidazole ring was non-zinc binding.

Green and efficient synthesis of new β-amido-aroyl carbonyl derivatives catalyzed by choline chloride/urea as a deep eutectic solvent

A green and highly efficient synthesis of some new β-amido-aroyl carbonyl derivatives has been achieved through a one-pot, three-component reaction of dimedone/barbituric acid derivatives, arylglyoxals, and amides in choline chloride/urea as a deep eutectic solvent (DES). The use of biodegradable materials, short reaction time and high yields of products introduced this protocol as an efficient environmentally friendly method. The DES could be easily recovered and reused about four times with satisfied catalytic activity.

Catalytic Asymmetric Darzens-Type Epoxidation of Diazoesters: Highly Enantioselective Synthesis of Trisubstituted Epoxides

Highly enantioselective Darzens-type epoxidation of diazoesters with glyoxal derivatives was accomplished using a chiral boron–Lewis acid catalyst, which facilitated asymmetric synthesis of trisubstituted α,β-epoxy esters. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction proceeded in high yield (up to 99 %) with excellent enantio- and diastereoselectivity (up to >99 % ee and >20:1 dr, respectively). The synthetic potential of this method was illustrated by conversion of the products to various compounds such as epoxy γ-butyrolactone, tertiary β-hydroxy ketone and epoxy diester.

Nature of the Nucleophilic Oxygenation Reagent Is Key to Acid-Free Gold-Catalyzed Conversion of Terminal and Internal Alkynes to 1,2-Dicarbonyls

2,3-Dichloropyridine N-oxide, a novel oxygen transfer reagent, allows the conductance of the gold(I)-catalyzed oxidation of alkynes to 1,2-dicarbonyls in the absence of any acid additives and under mild conditions to furnish the target species, including those derivatized by highly acid-sensitive groups. The developed strategy is effective for a wide range of alkyne substrates such as terminal- and internal alkynes, ynamides, alkynyl ethers/thioethers, and even unsubstituted acetylene (40 examples; yields up to 99%). The oxidation was successfully integrated into the trapping of reactive dicarbonyls by one-pot heterocyclization and into the synthesis of six-membered azaheterocycles. This synthetic acid-free route was also successfully applied for the total synthesis of a natural 1,2-diketone.

Antiproliferative Activity of 2-Aroyland 2-Heteroyl-1,1,3,3-Tetracyanoprop-2-en-1-ides

The influence of previously synthesized 2-aroyl-1,1,3,3-tetracyanoprop-2-en-1-ides on the growth of conditionally normal and tumor cells was studied in continuation of a search for new anticancer drugs. Cytotoxicities of the compounds were studied with respect to human tumor cell lines from the ATCC. All compounds were ineffective against melanoma and lung and ovary cancer cell lines and exhibited moderate activity in the other cases. The tested compounds exhibited highly selective effects because they were safe for conditionally normal skin fibroblasts.

Mono- or di-substituted imidazole derivatives for inhibition of acetylcholine and butyrylcholine esterases

Mono- or di-substituted imidazole derivatives were synthesized using a one-pot, two-step strategy. All imidazole derivatives were tested for AChE and BChE inhibition and showed nanomolar activity similar to that of the test compound donepezil and higher than that of tacrine. Structure activity relationship studies, docking studies to on X-ray crystal structure of AChE with PDB code 1B41, and adsorption, distribution, metabolism, and excretion (ADME) predictions were performed. The synthesized core skeleton was bound to important regions of the active site of AChE such as the peripheral anionic site (PAS), oxyanion hole (OH), and anionic subsite (AS). Selectivity of the reported test compounds was calculated and enzyme kinetic studies revealed that they behave as competitive inhibitors, while two of the test compounds showed noncompetitive inhibitory behavior. ADME predictions revealed that the synthesized molecules might pass through the blood brain barrier and intestinal epithelial barrier and circulate freely in the blood stream without binding to human serum albumin. While the toxicity of one compound on the WS1 (skin fibroblast) cell line was 1790 μM, its toxicity on the SH-SY5Y (neuroblastoma) cell line was 950 μM.

A simple route for synthesis of 5-(furan-3-yl)barbiturate/thiobarbiturate derivatives via a multi-component reaction between arylglyoxals, acetylacetone and barbituric/thiobarbituric acid

An effective protocol for the synthesis of 5-(furan-3-yl)barbiturate and 5-(furan-3-yl)thiobarbiturate derivatives through a one-pot three-component reaction of readily available starting materials arylglyoxals, barbituric acid or thiobarbituric acid and acetylacetone in water as solvent is reported.

INHIBITORS OF HEPATITIS C VIRUS REPLICATION

The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.

Exocyclic N-Acyliminium Ion (NAI) Cyclization: Access to Fully Substituted Oxazoles and Furocoumarins

A concise, one-pot route to oxazoles and furocoumarins has been reported. The key step in this transformation involves in situ generation of N-acyliminium ion (NAI) precursor under catalyst and solvent-free conditions and their further transformations promoted by superacid in the same pot. We have also presented the experimental evidence for the involvement of proto-solvated novel exocyclic N-acyliminium ion. Further, the UV-visible and fluorescence studies revealed that few of the compounds reported here exhibited emission of blue light upon irradiation in EtOH in the region of 404-422 nm.

Modular Synthesis of Di- A nd Trisubstituted Imidazoles from Ketones and Aldehydes: A Route to Kinase Inhibitors

A one-pot and modular approach to the synthesis of 2,4(5)-disubstituted imidazoles was developed based on ketone oxidation, employing catalytic HBr and DMSO, followed by imidazole condensation with aldehydes. This methodology afforded twenty-nine disubstituted NH-imidazoles (23%-85% yield). A three-step synthesis of 20 kinase inhibitors was achieved by employing this oxidation-condensation protocol, followed by bromination and Suzuki coupling in the imidazole ring to yield trisubstituted NH-imidazoles (23%-69%, three steps). This approach was also employed in the synthesis of known inhibitor GSK3037619A.