Oxindole

Oxindole
Names
	Preferred IUPAC name 1,3-Dihydro-2H-indol-2-one
Identifiers
CAS Number	59-48-3;
3D model (JSmol)	Interactive image;
Beilstein Reference	114692
ChEBI	CHEBI:31697;
ChEMBL	ChEMBL40823;
ChemSpider	284794;
ECHA InfoCard	100.000.390
EC Number	200-429-5;
Gmelin Reference	637057
KEGG	C12312;
MeSH	Oxindole
PubChemCID	321710;
RTECS number	NM2080500;
UNII	0S9338U62H;
CompTox Dashboard(EPA)	DTXSID80870389;
	InChI InChI=1S/C8H7NO/c10-8-5-6-3-1-2-4-7(6)9-8/h1-4H,5H2,(H,9,10) Key: JYGFTBXVXVMTGB-UHFFFAOYSA-N;
	SMILES c1ccc2c(c1)CC(=O)N2;
Properties
Chemical formula	C8H7NO
Molar mass	133.150g·mol−1
Appearance	pale yellow solid
Melting point	128 °C (262 °F; 401 K)
	Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa). Infobox references

Oxindole(2-indolone) is anaromatic heterocyclic organic compoundwith the formula C6H4CHC(O)NH. It has a bicyclic structure, consisting of a six-memberedbenzenering fused to a five-memberednitrogen-containing ring. Oxindole is a modifiedindolinewith a substituted carbonyl at the second position of the 5-member indoline ring. Classified as a cyclic amide, it is a pale yellow solid.

Formation and reactions

Oxindole is derived in nature fromtryptophan,formed by gut bacteria ( "normal flora" ). It is normally metabolized and detoxified from the body by the liver. In excess, it can cause sedation, muscle weakness, hypotension, and coma. Patients withhepatic encephalopathyhave been recorded to have elevated serum oxindole levels.^[1]

Treatment withphosphorus pentasulfidegives thethione.

Oxindoles

Rhynchophylline,a naturally occurring oxindole is a medicinal used as anNMDA antagonistand acalcium channel blocker.^[2]

Beyond, the parent compound, oxindoles include many compounds,^[3]for example 3-methyloxindole^[4]andsemaxanib.^[5]

References

^Riggio, Oliviero; Mannaioni, Guido; Ridola, Lorenzo; Angeloni, Stefania; Merli, Manuela; Carlà, Vincenzo; Salvatori, Filippo Maria; Moroni, Flavio (2 February 2010). "Peripheral and Splanchnic Indole and Oxindole Levels in Cirrhotic Patients: A Study on the Pathophysiology of Hepatic Encephalopathy".The American Journal of Gastroenterology.105(6): 1374–1381.doi:10.1038/ajg.2009.738.PMID 20125128.S2CID 20633097.
^Kang TH, Murakami Y, Matsumoto K, Takayama H, Kitajima M, Aimi N, Watanabe H (2002). "Rhynchophylline and Isorhynchophylline Inhibit NMDA Receptors Expressed inXenopusOocytes ".European Journal of Pharmacology.455(1): 27–34.doi:10.1016/S0014-2999(02)02581-5.PMID 12433591.
^Trost, Barry; Brennan, Megan (2009). "Asymmetric Syntheses of Oxindole and Indole Spirocyclic Alkaloid Natural Products".Synthesis.2009(18): 3003–3025.doi:10.1055/s-0029-1216975.
^Abraham S. Endler and Ernest I. Becker (1957). "3-Methyloxindole".Org. Synth.37:60.doi:10.15227/orgsyn.037.0060.
^Lubkoll, Jana; Millemaggi, Alessia; Perry, Alexis; Taylor, Richard J.K. (2010). "Tandem Horner–Wadsworth–Emmons/Heck procedures for the preparation of 3-alkenyl-oxindoles: The synthesis of Semaxanib and GW441756".Tetrahedron.66(33): 6606–6612.doi:10.1016/j.tet.2010.03.018.

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[1] Riggio, Oliviero; Mannaioni, Guido; Ridola, Lorenzo; Angeloni, Stefania; Merli, Manuela; Carlà, Vincenzo; Salvatori, Filippo Maria; Moroni, Flavio (2 February 2010). "Peripheral and Splanchnic Indole and Oxindole Levels in Cirrhotic Patients: A Study on the Pathophysiology of Hepatic Encephalopathy".The American Journal of Gastroenterology.105(6): 1374–1381.doi:10.1038/ajg.2009.738.PMID 20125128.S2CID 20633097.

[2] Kang TH, Murakami Y, Matsumoto K, Takayama H, Kitajima M, Aimi N, Watanabe H (2002). "Rhynchophylline and Isorhynchophylline Inhibit NMDA Receptors Expressed inXenopusOocytes ".European Journal of Pharmacology.455(1): 27–34.doi:10.1016/S0014-2999(02)02581-5.PMID 12433591.

[3] Trost, Barry; Brennan, Megan (2009). "Asymmetric Syntheses of Oxindole and Indole Spirocyclic Alkaloid Natural Products".Synthesis.2009(18): 3003–3025.doi:10.1055/s-0029-1216975.

[4] Abraham S. Endler and Ernest I. Becker (1957). "3-Methyloxindole".Org. Synth.37:60.doi:10.15227/orgsyn.037.0060.

[5] Lubkoll, Jana; Millemaggi, Alessia; Perry, Alexis; Taylor, Richard J.K. (2010). "Tandem Horner–Wadsworth–Emmons/Heck procedures for the preparation of 3-alkenyl-oxindoles: The synthesis of Semaxanib and GW441756".Tetrahedron.66(33): 6606–6612.doi:10.1016/j.tet.2010.03.018.

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