14922-36-2

Usage

Uses

Used in Pharmaceutical Industry:
4-Nitrophenylglyoxylic acid is used as an intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its role in the creation of bioactive compounds makes it a valuable asset in this field.
Used in Agricultural Chemicals:
4-NITROPHENYLGLYOXYLIC ACID is also utilized as an intermediate in the production of agricultural chemicals, playing a part in the development of products that can enhance crop protection and yield.
Used as a Reagent in Organic Synthesis:
4-Nitrophenylglyoxylic acid serves as a reagent in organic synthesis, facilitating various chemical reactions and contributing to the synthesis of complex organic molecules.
Used in Research for Biological Activities:
It is employed in research for its potential biological activities, such as antimicrobial and anticancer properties, aiding in the discovery and development of new treatments and therapies.
Used in Antimicrobial Applications:
4-Nitrophenylglyoxylic acid is studied for its antimicrobial properties, potentially serving as an agent to combat microbial infections.
Used in Anticancer Research:
4-NITROPHENYLGLYOXYLIC ACID is investigated for its anticancer properties, with the aim of identifying its potential to contribute to cancer treatment and management strategies.

InChI:InChI=1/C8H5NO5/c10-7(8(11)12)5-1-3-6(4-2-5)9(13)14/h1-4H,(H,11,12)

Upstream product

• 10098-39-2 2-hydroxy-2-(4-nitrophenyl)acetic acid 
• 100-12-9 4-ethylnitrobenzene 
• 131470-71-8 (5,6-Dihydro-[1,4]dioxin-2-yl)-(4-nitro-phenyl)-methanone 
• 65921-30-4 2-(4-nitrophenyl)-2-oxoethyl acetate 
• 7697-37-2 nitric acid 
• 57699-27-1 methyl p-nitrophenylglyoxylate 
• 100-19-6 (4-nitrophenyl)ethanone 
• 122-04-3 4-nitro-benzoyl chloride 
• 6048-20-0 4-nitrobenzoyl cyanide 

Downstream Products

• 57699-27-1 methyl p-nitrophenylglyoxylate 
• 147023-19-6 methyl 4-nitrobenzoylformate dimethylketal 
• 122709-97-1 (3,4-Dihydro-1H-isoquinolin-2-yl)-(4-nitro-phenyl)-methanethione 
• 105248-77-9 4-nitro-α-oxophenylacetyl chloride 
• 128742-83-6 3-(1-Methyl-1H-indol-3-yl)-4-(4-nitro-phenyl)-furan-2,5-dione 
• 135386-34-4 allyl 4-nitrophenylglyoxylate 
• 87736-10-5 5-Hydroxy-6-(4-nitro-phenyl)-pyrazine-2,3-dicarbonitrile 
• 959161-41-2 S-t-butyl hydroxy-(4-nitrophenyl)-thioacetate 
• 959161-59-2 S-t-butyl (4-nitrophenyl)-oxo-thioacetate 
• 87736-26-3 5-Chloro-6-(4-nitro-phenyl)-pyrazine-2,3-dicarbonitrile 
• 86997-04-8 5-(4-Nitrophenyl)-2-phenyl-6H-1,3,4-oxadiazin-6-on 
• 1036242-06-4 C₂₂H₁₆N₄O₄ 
• 1428848-34-3 (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2,2-dihydroxy-2-(4-nitrophenyl)acetoxy)ethyl)-pyridine 1-oxide 
• 431059-81-3 N,N‐dimethyl‐2‐(4‐nitrophenyl)‐2‐oxoacetamide 

Relevant academic research and scientific papers

Novel α-ketoamide based diazeniumdiolates as hydrogen peroxide responsive nitric oxide donors with anti-lung cancer activity

A novel type of hydrogen peroxide (H2O2)-activated diazeniumdiolate based on an α-ketoamide moietey was developed as a nitric oxide (NO) donor. KA-NO-4 inhibited lung cancer cells with submicromolar activity. The H2O2

Novel peptidomimetic peptide deformylase (PDF) inhibitors of Mycobacterium tuberculosis

Emergence of MDR-TB and XDR-TB led to the failure of available anti-tubercular drugs. In order to explore, identify and develop new anti-tubercular drugs, novel peptidomimetic series of Mtb–peptide deformylase (PDF) inhibitors was designed and synthesized. In vitro antimycobacterial potential of compounds was established by screening of compounds against Mycobacterium tuberculosis H37Rv strain using MABA. Among them, ester series of compounds 4a, 4b, 4c, 4d, and 4e were found most active, with compound 4c being highly active and exhibiting minimum inhibitory concentration of 6.25?μg/ml against M.?tb H37Rv strain. Additionally, the compounds were docked to determine the probable binding interactions and understand the mechanism of action of most active molecules on Mtb-peptide deformylase (PDF), which is involved in the mycobacterium protein synthesis.

K2S2O8mediated synthesis of 5-Aryldipyrromethanes and meso-substituted A4-Tetraarylporphyrins

The synthesis of dipyrromethanes from pyrrole and arylglyoxylic acids in the presence of K2S2O8at 90 C is reported affording dipyrromethanes in very good yields. Unlike an excess pyrrole traditionally used in dipyrromethane synthesis, the current method uses a stoichiometric amount of pyrrole avoiding any use of Br?nsted or Lewis acid. A gram scale synthesis of 5-phenyldipyrromethane is also achieved demonstrating potential scale up of dipyrromethanes using this method feasible. Subsequently, dipyrromethanes were converted to A4tetraarylporphyrins also in the presence of K2S2O8at 90C. A direct synthesis of A4-tetraphenylporphyrin from excess pyrrole and phenylglyoxylic acid in the presence of K2S2O8 at 90C is also reported.

Minisci aroylation of N-heterocycles using choline persulfate in water under mild conditions

Metal persulfate mediated thermal oxidative organic transformations invariably require a higher temperature and frequently use an organic solvent. The objective of this work was to develop persulfate mediated oxidative transformations that can be performed nearly at room temperature using water as a solvent. This report describes modified Minisci aroylation of isoquinolines with arylglyoxylic acids using choline persulfate and its pre-composition (choline acetate and K2S2O8) in water at 40 °C. A few other nitrogen heterocycles were also utilized affording various aroylated products in good to excellent yields. Unlike metal persulfate that could produce metal salt byproducts, a key feature of the chemistry reported herein includes the use of environmentally benign choline persulfate containing biodegradable choline as a counter-cation, the Minisci reaction demonstrated at 40 °C in water as the only solvent, and unconventional activation of persulfate. This journal is

Aroylation of Electron-Rich Pyrroles under Minisci Reaction Conditions

The development of Minisci acylation on electron-rich pyrroles under silver-free neutral conditions has been reported featuring the regioselective monoacylation of (NH)-free pyrroles. Unlike conventional Minisci conditions, the avoidance of any acid that could result in the polymerization of pyrroles was the key to success. The umpolung reactivity of the nucleophilic acyl radical, generated in situ from arylglyoxylic acid, could help explain the mechanism of product formation with electron-rich pyrroles. Alternatively, the nucleophilic substitution of the acyl radical on the electron-deficient pyrrole radical cation is proposed.

A near-infrared fluorescent probe for endogenous hydrogen peroxide real-time imaging in living cells and zebrafish

Hydrogen peroxide (H2O2) can be produced in mitochondria and plays a significant role in physiological metabolism. Overproduction of H2O2 is a hallmark of many diseases. Therefore, it is very important to develop a highly sensitive method for detecting H2O2 both in vivo and in vitro. Previously reported benzil-based fluorescence probes are superior to those based on boronate ester in terms of reaction selectivity. However, the near-infrared (NIR) probe with biocompatibility has been rarely reported for the detection of endogenous hydrogen peroxide and the real-time imaging in biological system. Hemicyanine skeleton has been proven to be effective scaffold for NIR fluorescent probes for non-invasive optical imaging in vivo. In this paper, a Cy-H2O2 probe for real-time monitoring hydrogen peroxide in organisms was designed by modifying the NIR hemicyanine framework with benzil moiety. The results showed that Cy-H2O2 exhibits high specificity and sensitivity, and has good water solubility and short response time (within 10 min) for detection of hydrogen peroxide in vitro and in vivo. The reaction mechanism was deduced by detecting product of the fluorescent probe reacting with hydrogen peroxide using HPLC. The probe shows a good linear relationship for the specific response to H2O2 within the concentration range of 0–7 μM and the detection limit is 65 nM. In addition, the probe Cy-H2O2 has been successfully applied to H2O2 detection in living cells and zebrafish.

Introduction of the α-ketoamide structure: En route to develop hydrogen peroxide responsive prodrugs

Leveraging the elevated levels of hydrogen peroxide (H2O2) in cancer, inflammatory diseases and cardiovascular disorders, H2O2-activated promoieties have been widely used in drugs and biomaterials design. However, the overwhelming majority of the promoieties only share the common structure of a H2O2-responsive arylboronic acid/ester moiety with low diversity. We report here an unprecedented strategy to construct novel H2O2-responsive prodrugs based on an α-ketoamide structure. As a proof of concept, we designed and synthesized a panel of α-ketoamide based nitrogen mustard prodrugs, among which KAM-2 showed potent growth inhibitory activity and high selectivity toward cancer cells. The H2O2-trigged decomposition of KAM-2 was validated, and the DNA damaging and apoptosis promoting activity attributed to the released nitrogen mustard were demonstrated. Our work unveils α-ketoamide as a new scaffold for prodrug design and may quickly inspire future developments.

Copper-catalyzed coupling of anthranils and α-keto acids: Direct synthesis of α-ketoamides

Copper-catalyzed coupling of α-keto acids with anthranils is reported for the synthesis of α-ketoamides. This process involves N-O/C-O bond cleavages and C-N bond formation. Furthermore, the decarboxylation of α-keto acids can be successfully suppressed under redox-neutral conditions.

Hydrogen peroxide-responsive nitrogen mustard anti-tumor pro-drug and preparation method thereof

The invention discloses a hydrogen peroxide-responsive nitrogen mustard anti-tumor pro-drug and a preparation method thereof, and belongs to the field of pharmaceutical chemistry. The compound contains an alpha-ketoamide structure and a nitrogen mustard structure, can rapidly respond to H2O2, can be used as the nitrogen mustard anti-tumor pro-drug, has good response effect to H2O2, has high cell selectivity and small toxic and side effects, provides an effective, safe and highly selective anti-tumor drug, enriches the types of nitrogen mustard anti-tumor drugs, and has a good market prospect.

Hydrogen peroxide responsive azo onium glycol salt compound and application thereof (by machine translation)

The invention discloses a hydrogen peroxide responsive azo onium glycol salt compound and application thereof, and, belongs to the field α - of pharmaceutical chemistry, H. 2 O2 The structure NO, provided by the invention can realize specific inhibition on different types of tumor, cells and has a very good, market prospect for the tumor cell selectivity and, the low toxic and NO side effect, and can be used as a. new-type medicine with a tumor cell selectivity and a small toxic and side effect. (by machine translation)