1132-40-7

Usage

Uses

Used in Research Applications:
2-HYDROXYIMINO-N-P-TOLYL-ACETAMIDE is used as a nitric oxide (NO) scavenger for studying the biological functions of NO in various research settings. It helps researchers understand the role of NO in physiological processes and its impact on health and disease.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 2-HYDROXYIMINO-N-P-TOLYL-ACETAMIDE is used as a starting point for the design of new drug molecules. Its properties as a NO scavenger and radical scavenger make it a promising candidate for the development of treatments for cardiovascular diseases and neurological disorders, where NO imbalances are implicated.
Used in Medicine:
2-HYDROXYIMINO-N-P-TOLYL-ACETAMIDE has potential applications in medicine, particularly for the treatment of conditions related to nitric oxide imbalance. Its ability to modulate NO levels can be harnessed to develop therapeutics for a range of diseases, including but not limited to cardiovascular and neurological disorders.

InChI:InChI=1/C9H10N2O2/c1-7-2-4-8(5-3-7)11-9(12)6-10-13/h2-6,13H,1H3,(H,11,12)/b10-6+

Upstream product

• 302-17-0 chloral hydrate 
• 106-49-0 p-toluidine 
• 75-87-6 chloral 
• 448248-25-7 2,2,2-trichloro-1-p-toluidino-ethanol 
• 540-23-8 p-toluidine hydrochloride 
• 515-83-3 chloral ethyl hemiacetal 

Downstream Products

• 608-05-9 5-methyl-indole-2,3-dione 
• 70452-31-2 5-methyl-3-(2-oxo-2-phenylethylidene)indolin-2-one 
• 1020975-73-8 C₁₆H₁₂FNO₂ 
• 1161792-74-0 C₁₇H₁₅FN₄OS 
• 1332508-67-4 C₂₂H₁₇NO₄ 
• 1332508-68-5 C₂₃H₁₉NO₅ 
• 1332508-69-6 C₂₃H₁₉NO₄ 
• 1332508-70-9 C₂₂H₁₆N₂O₆ 
• 1332508-71-0 C₂₃H₁₉NO₄ 
• 1332508-72-1 C₂₃H₁₈N₂O₆ 
• 1332508-73-2 C₂₃H₁₉NO₄ 
• 1332508-75-4 C₂₄H₂₁NO₄ 
• 1020957-54-3 2-(5-methyl-2,3-dioxoindolin-1-yl)-N-phenylacetamide 
• 99448-75-6 1-benzyl-5-methylindoline-2,3-dione 

Relevant academic research and scientific papers

Design and synthesis of 3-substituted indolin-2-one derivatives with methyl (e)-2-(3-Methoxy) acrylate moiety

In this article, fifteen indolin-2-one derivatives with methyl (E)-2-(3-methoxy)acrylate group were designed and synthesized. The structures of target compounds were confirmed by 1H NMR, IR and HR-MS spectra analysis.

Isatins inhibit cyclooxygenase-2 and inducible nitric oxide synthase in a mouse macrophage cell line

Isatin is a versatile compound with a diversity of effects. We designed to investigate the inhibitory effect of isatin derivatives on lipopolysaccharide/interferon-γ-induced expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) proteins, production of prostaglandin E2 (PGE2), nitric oxide (NO), tumor necrosis factor (TNF-α), and their capacity to scavenge NO. Isatins inhibit TNF-α production and iNOS and COX-2 protein expression resulting on reduced levels of NO and PGE2. Our results indicate isatin and it derivatives as inhibitors of iNOS and COX-2 enzymes, which might be used as anti-inflammatory and antitumoral agents.

The mechanism of Sandmeyer's cyclization reaction by electrospray ionization mass spectrometry

Using electrospray ionization (tandem) mass spectrometry (ESI-MS(/MS)) spectrometric experiments, the Sandmeyer reaction was monitored on-line, and key intermediates were intercepted and characterized for the first time. The mechanistic information provided by on-line ESI-MS(/MS) is in accordance with Sandmeyer's proposal, and was made possible by coupling a microreactor on-line to the ESI ion source, which allowed reactions to be screened from 0.7-2.0 s, identifying and characterizing all intermediates that were formed and consumed during the reaction. Copyright

Design, synthesis and in vitro cytotoxicity evaluation of 5-(2-carboxyethenyl)isatin derivatives as anticancer agents

Forty four di- or trisubstituted novel isatin derivatives were designed and synthesized in 5-6 steps in 25-45% overall yields. Their structures were confirmed by 1H NMR and 13C NMR as well as LC-MS. The anticancer activity of these new isatin derivatives against three human tumor cell lines, K562, HepG2 and HT-29, were evaluated by MTT assay in vitro. SAR studies suggested that the combination of 1-benzyl and 5-[trans-2- (methoxycarbonyl)ethen-1-yl] substitution greatly enhance their cytotoxic activity, whereas an intact carbonyl functionality on C-3 as present in the parent ring is required to such a potency. This study leads to the identification of two highly active molecules, compounds 2h (IC50 = 3 nM) and 2k (IC50 = 6 nM), against human leukemia K562 cells.

Microwave assisted preparation of isatins and synthesis of (±)- convolutamydine-A

Microwave assisted preparation of a number of isatin derivatives is reported. A simple synthesis of (±)-convolutamydine-A, a potent compound against leukemia cells, is presented.

Design, synthesis and preliminary biological evaluation of indoline-2,3-dione derivatives as novel HDAC inhibitors

Histone deacetylases (HDACs) are zinc-dependent or NAD+ dependent enzymes and play a critical role in the process of tumor development. Herein a series of indoline-2,3-dione derivatives have been designed and synthesized as potential HDACs inhibitors. The preliminary biological evaluation showed that most compounds synthesized have exhibited moderate Hela cell nuclear extract inhibitory activities, among which compound 25a (IC50 = 10.13 nM) has shown the best efficacy. The anti-proliferative activities of some of these compounds were also discussed.

A cinchona alkaloid catalyzed enantioselective sulfa-Michael/aldol cascade reaction of isoindigos: Construction of chiral bispirooxindole tetrahydrothiophenes with vicinal quaternary spirocenters

A cinchona alkaloid catalyzed diastereoselective and enantioselective sulfa-Michael/aldol cascade reaction between 1,4-dithiane-2,5-diol and isoindigos has been successfully developed to afford the highly congested bispirooxindole tetrahydrothiophenes with vicinal quaternary spirocenters in high yields (up to 91%), excellent diastereoselectivities (up to >20 : 1 dr), and good enantioselectivities (up to 98% ee). Some synthetic transformations of the reaction products were also studied.

A modified Sandmeyer methodology and the synthesis of (±)-convolutamydine A

(±)-Convolutamydine A (5) has been prepared by it concise synthesis from 3,5-dibromoaniline using a modified Sandmeyer methodology. The modified Sandmeyer methodology has also been found to be beneficial for the synthesis of other α-isonitrosoacetanilides. The 4,6-dibromohydroxyoxindole nucleus was further confirmed by comparison with the isomeric 5,7-dibromohydroxyoxindole.

Discovery of di-indolinone as a novel scaffold for protein tyrosine phosphatase 1B inhibitors

A series of di-indolinone derivatives was designed and synthesized to optimize our lead compounds basing on molecular docking study as PTP1B inhibitors. Successive enzymatic assay identified the synthetic di-indolinone as novel PTP1B inhibitors with low micromole-ranged inhibitory activity and at least several-fold selectivity over other tested homologous PTPs.

Study on synthesis of some substituted N-propargyl isatins by propargylation reaction of corresponding isatins using potassium carbonate as base under ultrasound- and microwave-assisted conditions

Substituted N-propargyl isatins were synthesized by SN2 reaction of corresponding substituted isatins with propargyl bromide in the presence of anhydrous K2CO3 as base. We reported about study on systematically synthesis of these compounds using heating procedures under different reaction conditions, including microwave-assisted heating conditions at power of 100?W (Procedure A), conventional heating conditions in water bath at 50?°C in acetonitrile (Procedure B), and conventional heating conditions in water bath at 50?°C in DMF (procedure C). The best procedure A was deduced based on the investigations on the reaction conditions. Almost all substituted N-propargyl isatins were new, except compounds with R of H, 5-Me, 5-Cl and 5-Br substituents. The structures of the obtained compounds were confirmed by the modern spectroscopic methods.