Oxindole

Base Information

• Chemical Name: Oxindole
• CAS No.: 59-48-3
• Molecular Formula: C8H7NO
• Molecular Weight: 133.15
• Hs Code.: 2933.99
• European Community (EC) Number: 200-429-5
• NSC Number: 274863
• UNII: 0S9338U62H
• DSSTox Substance ID: DTXSID80870389
• Nikkaji Number: J1.393E
• Wikipedia: Oxindole
• Wikidata: Q2018788
• Metabolomics Workbench ID: 54435
• ChEMBL ID: CHEMBL40823
• Mol file: 59-48-3.mol

Synonyms:2-Indolinone(7CI,8CI);Oxindole (6CI);1,3-Dihydro-2H-indol-2-one;1,3-Dihydroindol-2-one;2-Indolone;2-Oxindole;2-Oxo-2,3-dihydroindole;2-Oxoindole;2-Oxoindoline;Indol-2(3H)-one;Indoline-2-one;NSC 274863;Oxindol;

Chemical Property of Oxindole

Chemical Property:

• Appearance/Colour: beige to yellowish-orange or pinkish-brown powder
• Vapor Pressure: 0.000521mmHg at 25°C
• Melting Point: 123-128 °C(lit.)
• Refractive Index: 1.586
• Boiling Point: 312.7 °C at 760 mmHg
• PKA: 14.77±0.20(Predicted)
• Flash Point: 177.8 °C
• PSA: 29.10000
• Density: 1.198 g/cm³
• LogP: 1.31920
• Storage Temp.: Refrigerator
• Solubility.: 9.1g/l
• Water Solubility.: insoluble
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 133.052763847
• Heavy Atom Count: 10
• Complexity: 155

Purity/Quality:

99% ^*data from raw suppliers

Oxindole(2-Indolone) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Indoles
• Canonical SMILES: C1C2=CC=CC=C2NC1=O
• Description: Oxindole, a bicyclic monoterpene alkaloid, exhibits a simple, viable yet challenging synthesis approach, though it undoubtedly forms the core of a class of biologically important compounds. Most often found naturally, being a tryptophan derivative, it is produced in the human body in the gut by ‘normal flora’ bacteria as well, hence getting the name- ‘Human metabolite of Indole’. Many derivatives of oxindole are also obtained from habitual plant-based sources, which later became an ingredient in several traditional or ‘folk’ medicinal practices. Amongst derivaices containing oxindole core, one of the simplest subclasses of oxindoles is 3-alkenyl-oxindoles, nearly all of them are obtained from natural sources. The first known indigenously occurring 3-alkenyl-oxindoles were extracted and isolated from the subterranean plant stem or ‘rhizomes’ of the perennial Cimicifuga dahurica plant, from the Cimicifuga dry rootstock species, around half a century ago, in the year 1978. Other derivatives in traditional medical use, till date, include 2-indolinone type of oxindoles, used extensively as antipyretic agents.
• Uses and Mechanism of Action: Traditionally, oxindole has been reported to be used in the treatment of infection, cancer, gastric ulcers, arthritis and other inflammatory processes. Oxindole has been shown to be a pharmacologically advantageous scaffold having many biological properties that are relevant to medicinal chemistry. The simplicity and widespread occurrence of this scaffold in plant-based alkaloids have further reinforced oxindole’s merit in the domain of novel drug discovery. First extracted from Uncaria tomentosa, commonly the known as cat claw’s plant which was found abundantly in the Amazon rainforest, molecules with the oxindole moiety have been shown to be common in a wide variety of compounds extracted from plant sources. The role of oxindole as a chemical scaffold for fabricating and designing biological drugs agents can be ascribed to its ability to be modified by a number of chemical groups to generate novel biological functions. Oxindole nucleus obtained from synthetic or natural origin exhibited an extensive range of biological activities. Owing to its diverse pharmacological profile, industry and academia have shown huge interest in developing novel synthetic oxindole derivatives with fascinating biological activities. This progress towards synthetic oxindole derivatives has lead to development of a marketed anti-cancer agent Sunitinib implicated in gastrointestinal stromal tumours and metastatic renal cell cancer. Further optimization of the substituents around the oxindole nucleus resulted in several oxindole based kinase inhibitors that are in clinical trials including SU11248, SU5416, SU5614, SU6668, SU14813, SU4984 etc. The oxindole derivatives Indolidan and Adibendan have also been used for the treatment of congestive heart failure due to their strong vasodilatory, ionodilatory and positive ionotropic effects. Besides, 3-substituted and spiro-oxindole derivatives have been implicated in wide spectrum of biological activities including anti-tumour, antioxidant, anti-alzheimer's, kinase inhibitory activity, β3 adrenergic receptor agonist, anti-bacterial, neuroprotective, spermicidal, analgesic activity, etc.
• Production Methods: Being ubiquitous in nature, oxindole has been found in tissues and fluids of mammals as well as natural products produced by a range of plants, bacteria and invertebrates. The oxindole in form of alkaloids are extracted from the cat claw's plant Uncaria tomentosa which is woody, tropical vine indigenous to the Amazon rainforest and other tropical areas of South and Central America. Over the past several decades, novel transition-metal-catalyzed methodologies have been applied toward the synthesis of a variety of heterocycles. Methods exploiting the unique reactivity of palladium, nickel, copper, rhodium, and ruthenium catalysts to develop methods toward a wide array of oxindole scaffolds has been developed.
• References: [1] Oxindole and its derivatives: A review on recent progress in biological activities; DOI 10.1016/j.biopha.2021.111842; [2] Oxindole: A chemical prism carrying plethora of therapeutic benefits; DOI 10.1016/j.ejmech.2016.08.011; [3] Metal-Catalyzed Approaches toward the Oxindole Core; DOI 10.1021/acs.accounts.0c00297

Technology Process of Oxindole

There total 172 articles about Oxindole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

methyl (2-nitrophenyl)acetate (30095-98-8) → 2-oxoindole (59-48-3)

Guidance literature:

methyl (2-nitrophenyl)acetate; With hydrogen; In ethyl acetate; at 20 ℃; for 24h; under 7600.51 Torr; Autoclave;

In ethyl acetate; for 6h; Reflux; Molecular sieve;

DOI:10.1021/ol9001366

Reference yield: 98.0%

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) → 2-oxoindole (59-48-3)

Guidance literature:

indole-2,3-dione; With hydrazine; In methanol; Heating;

With sodium ethanolate; In ethanol; Further stages.; Heating;

DOI:10.1021/ol016379r

Reference yield: 95.0%

2-(2-nitrophenyl)acetic acid (3740-52-1) → 2-oxoindole (59-48-3)

Guidance literature:

With iron; acetic acid; at 100 ℃;

DOI:10.1016/j.ejmech.2015.10.020

upstream raw materials:

tetrachloromethane

2'-chloro-benzeneacetic acid

dioxindol

spiro[[1,3]dithiolane-2,3'-indolin]-2'-one

Downstream raw materials:

3-(2-amino-benzylidene)-1,3-dihydro-indol-2-one

(3E)-3-(2-furylmethylidene)-1H-indol-2(3H)-one

indirubin

3-(3-oxo-3H-benzo[b]thiophen-2-ylidene)-1,3-dihydro-indol-2-one

Refernces

• 1、 Avula, Vijay Kumar Reddy,Chintha, Venkata Ramaiah,Vallela, Swetha,Anireddy, Jaya Shree,Chamarthi, Naga Raju,Wudayagiri, Rajendra. "Synthesis, Docking, and Bioavailability of 2′-Oxo-3-phenylspiro[cyclopropane-1,3′-indoline]-2,2-dicarbonitriles as Antibacterial Agents In Silico". . p. 209 - 217. Retrieved 2019.
• 2、 Kungumathilagam,Karunakaran. "Kinetics and mechanism of meso-tetraphenylporphyriniron(III) chloride catalyzed oxidation of indole by peroxomonosulphate". . p. 4311 - 4314. Retrieved 2013.
• 3、 Meenakshisundaram, Subbiah,Sarathi. "Kinetics and mechanism of oxidation of indole by HSO5 -". . p. 46 - 51. Retrieved 2007.
• 4、 Mansour, Hany S.,Abd El-Wahab, Hend A. A.,Ali, Ahmed M.,Aboul-Fadl, Tarek. "Inversion kinetics of someE/Z3-(benzylidene)-2-oxo-indoline derivatives and theirin silicoCDK2 docking studies". . p. 7839 - 7850. Retrieved 2021/03/03.
• 5、 Huang, Tiao,Kong, Dulin,Li, Yue,Liu, Li,Wu, Mingshu. "A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids". . p. 2321 - 2328. Retrieved 2021/09/22.