20870-79-5

Usage

Uses

Used in Pharmaceutical Industry:
5-NITROOXINDOLE is used as a reactant for the synthesis of 3-[4-(amino/methylsulfonyl)phenyl]methylene-indolin-2-one derivatives, which are novel COX-1/2 and 5-LOX inhibitors. These inhibitors have potential applications in the treatment of inflammation and pain.
5-NITROOXINDOLE is also used as a reactant for the preparation of Aurora kinase inhibitors. Aurora kinases are key regulators of cell division and are often overexpressed in cancer cells, making them an attractive target for cancer therapy.
In the field of oncology, 5-NITROOXINDOLE is used as a reactant for the synthesis of 3-substituted 2-indolinone RET inhibitors. RET is a receptor tyrosine kinase that is frequently mutated or overexpressed in various types of cancer, and its inhibition can help in the treatment of these diseases.
5-NITROOXINDOLE is used as a reactant for the synthesis of 4-azachromeno[2,3-b]indol-11(6H)-ones and their derivatives, which are analogs of the anti-cancer drug ellipticine. These compounds have potential applications in the treatment of various types of cancer due to their ability to interact with DNA and inhibit topoisomerase II.
In the field of medical imaging, 5-NITROOXINDOLE is used as a reactant for the preparation of [18F]fluorobenzylidene-indolinone, a potential tyrosine kinase inhibitor for PET (positron emission tomography) tumor imaging. 5-NITROOXINDOLE can help in the detection and monitoring of cancer progression.
Lastly, 5-NITROOXINDOLE is used as a reactant for the preparation of 3-substituted indolin-2-ones, which have potential applications as neuroprotective and toxic agents. These compounds can be used in the development of drugs targeting neurological disorders and conditions.

InChI:InChI=1/C8H6N2O3/c11-8-4-5-3-6(10(12)13)1-2-7(5)9-8/h1-3H,4H2,(H,9,11)

Upstream product

• 59-48-3 2-oxoindole 
• 4036-14-0 5-Nitro-3-diazo-1,3-dihydro-2H-indol-2-one 
• 870-85-9 ethyl 3-methylaminocrotonate 
• 6146-52-7 5-nitroindole 
• 611-09-6 5-nitroisatin 
• 100-01-6 4-nitro-aniline 
• 79-04-9 chloroacetyl chloride 
• 3740-52-1 2-(2-nitrophenyl)acetic acid 
• 62-53-3 aniline 
• 91-56-5 indole-2,3-dione 
• 42366-35-8 hydroxyimino-N-phenylacetamide 
• 612-53-3 (E)-3-iminoindolin-2-one 
• 113423-47-5 3,3-dibromo-5-nitro-indolin-2-one 

Downstream Products

• 110335-70-1 3-(4-diethylamino-phenylimino)-5-nitro-indolin-2-one 
• 116339-27-6 5-nitro-indoline-2,3-dione-3-phenylhydrazone 
• 114985-63-6 1-acetyl-5-nitroindol-2-one 
• 20876-36-2 5-amino-1,3-dihydro-2H-indol-2-one 
• 107315-71-9 2,3-dihydro-5-nitro-2-oxo-N-phenyl-1H-indole-1-carboxamide 
• 23872-30-2 5-Nitro-3-dimethylaminomethylen-oxindol 
• 159212-47-2 3-[1-Dimethylamino-meth-(E)-ylidene]-5-nitro-1,3-dihydro-indol-2-one 
• 301700-15-2 5-nitro-2-phenoxycarbonyloxy-indole-1-carboxylic acid phenyl ester 
• 850718-37-5 5-nitro-3-[1-(imidazol-4-yl)ethylidene]indolin-2-one 
• 1261153-02-9 (E)-5-nitro-3-[[4-(sulfamoyl)phenyl]methylene]indolin-2-one 
• 1261152-88-8 (E)-5-nitro-3-[[4-(methylsulfonyl)phenyl]methylene]indolin-2-one 
• 1415668-19-7 1',3'-di(4-methoxyphenyl)-5-nitro-2',3',4',6'-tetrahydro-1'H-spiro[indoline-3,5'-pyrimidin]-2-one 
• 1629164-53-9 (E)-3-((6-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl)methylene)-5-nitroindolin-2-one 
• 1629164-59-5 (E)-3-((6-(4-chlorophenyl)-2-(3,4,5-trimethoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl)methylene)-5-nitroindolin-2-one 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of 2-indolinone derivatives as PAK1 inhibitors in MDA-MB-231 cells

P21-activated kinase 1 (PAK1) plays a vital role in the proliferation, survival and migration of cancer cells, which has emerged as a promising drug target for cancer therapy. In this study, a series of 2-indolinone derivatives were designed and synthesized through a structure-based strategy. A potent PAK1 inhibitor (ZMF-005) was discovered, which presented an IC50 value of 0.22 μM against PAK1 with potent antiproliferative activity. Furthermore, we predicted the binding mode of ZMF-005 and PAK1 by molecule docking and dynamic (MD) simulation. In addition, ZMF-005 was documented to induce significant apoptosis and suppress migration in MDA-MB-231 cells. Collectively, these findings revealed that ZMF-005 is a novel potent PAK1 inhibitor for breast cancer treatment.

New cell cycle checkpoint pathways regulators with 2-Oxo-indoline scaffold as potential anticancer agents: Design, synthesis, biological activities and in silico studies

3-Arylidene-2-oxo-indoline derivatives are at the heart of a wide range of clinically, medicinally and biologically important compounds among the 2-oxo-indolines. A number of 3-arylidene-2-oxo-indolines have been approved for clinical application. Accordi

Towards multi-target antidiabetic agents: In vitro and in vivo evaluation of 3,5-disubstituted indolin-2-one derivatives as novel α-glucosidase inhibitors

Type 2 diabetes mellitus is a chronic progressive disease that usually requires polypharmacological treatment approaches. Previously we have described a series of 2-oxindole derivatives as GSK3β inhibitors with in vivo antihyperglycemic activity. α-Glucos

Inversion kinetics of someE/Z3-(benzylidene)-2-oxo-indoline derivatives and theirin silicoCDK2 docking studies

The structure-based design of some CDK2 inhibitors with a 3-(benzylidene)indolin-2-one scaffold as potential anticancer agents was realized. Target compounds were obtained asE/Zmixtures and were resolved to correspondingE- andZ-diastereomers.In silicostudies using MOE 2019.01 software revealed better docking on the targeted enzyme for theZ-diastereomer compared to theE-one. A time-dependent kinetic isomerization study was carried out for the inversion ofE/Zdiastereomers in DMSO-d6at room temperature, and were found to obey the first order kinetic reactions. Furthermore, a determination of the kinetic inter-conversion rate order by graphical analysis method and calculation of the rate constant and half-life of this kinetic process were carried out. For the prediction of the stability of the diastereomer(s), a good multiple regression equation was generated between the reaction rates of isomerization and some QM parameters with significantpvalue.

A Unified Catalytic Asymmetric (4+1) and (5+1) Annulation Strategy to Access Chiral Spirooxindole-Fused Oxacycles

A unified catalytic asymmetric (N+1) (N=4, 5) annulation reaction of oxindoles with bifunctional peroxides has been achieved in the presence of a chiral phase-transfer catalyst (PTC). This general strategy utilizes peroxides as unique bielectrophilic four- or five-atom synthons to participate in the C?C and the subsequent umpolung C?O bond-forming reactions with one-carbon unit nucleophiles, thus providing a distinct method to access the valuable chiral spirooxindole-tetrahydrofurans and -tetrahydropyrans with good yields and high enantioselectivities under mild conditions. DFT calculations were performed to rationalize the origin of high enantioselectivity. The gram-scale syntheses and synthetic utility of the resultant products were also demonstrated.

A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids

A novel method for the synthesis of 3-monohalooxindoles by acidolysis of isatin-derived 3-phosphate-substituted oxindoles with haloid acids was developed. This synthetic strategy involved the preparation of 3-phosphate-substituted oxindole intermediates and SN1 reactions with haloid acids. This new procedure features mild reaction conditions, simple operation, good yield, readily available and inexpensive starting materials, and gram-scalability.

2-indolone PAK1 inhibitor and application of 2-indolone PAK1 inhibitor in anti-tumor treatment drugs

The invention relates to a 2-indolone PAK1 inhibitor and an application of the 2-indolone PAK1 inhibitor in anti-tumor treatment drugs, and belongs to the technical field of anti-tumor pharmacy. The technical problem to be solved by the invention is to provide a compound used as a PAK1 inhibitor. The compound comprises a compound as shown in the specification or pharmaceutically acceptable salt thereof, wherein X, n and R1 are described in the claims and the specification. The compound or the pharmaceutically acceptable salt thereof can be used as a PAK1 inhibitor for preparing antitumor drugs.

Synthesis and biological evaluation of 3-substituted 2-oxindole derivatives as new glycogen synthase kinase 3β inhibitors

Glycogen synthase kinase 3β (GSK-3β) is a widely investigated molecular target for numerous diseases including Alzheimer's disease, cancer, and diabetes mellitus. Inhibition of GSK-3β activity has become an attractive approach for treatment of diabetes and cancer. We report the discovery of novel GSK-3β inhibitors of 3-arylidene-2-oxindole scaffold with promising activity. The most potent compound 3a inhibits GSK-3β with IC50 4.19 nM. In a cell-based assay 3a shows no significant leucocyte toxicity at 10 μM and is moderately cytotoxic against A549 cells. Compound 3a demonstrated high antidiabetic efficacy in obese streptozotocin-treated rats improving glucose tolerance at a dose of 50 mg/kg body weight thus representing an interesting lead for further optimization.

Synthesis of 2-Oxindoles from Substituted Indoles by Hypervalent-Iodine Oxidation

A practical conversion of indoles into the corresponding 2-oxindoles is achieved efficiently using a hypervalent iodine reagent. This oxidation is amenable to different substituted indoles, and allows the synthesis of a wide range of synthetically valuable substituted 2-oxindoles in up to 90 % yield. Furthermore, Ropinirole, a drug used to alleviate the symptoms of Parkinson's disease, was synthesized in three steps in an overall yield of 44 % using this method.

Method for directly synthesizing substituted 2-indolone by substituted indole under neutral condition

The invention relates to a method for directly synthesizing substituted 2-indolone by substituted indole under the neutral condition. The method comprises the following steps of sequentially adding organic solvents and water according to the proportion of 1:1-1:20 at the room temperature; then, adding high-iodine reagents; raising the temperature to 40 to 160 DEG C; then, adding indole; performingreaction for 1 to 8 hours to obtain the substituted 2-indolone compounds. The method has the main innovation point that under the neutral condition, substituted 2-indolone is directly synthesized through indole oxidization; the use of strong acid reagents is avoided. The method has the advantages that the raw materials are cheap and can be easily obtained; the operation is simple and convenient;the substrate universality is high; the reaction yield is high, and the like.