Oxindole

Last updated
Oxindole
Oxindole.png
Oxindole-3D-balls.png
Names
Preferred IUPAC name
1,3-Dihydro-2H-indol-2-one
Identifiers
3D model (JSmol)
114692
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.390 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-429-5
637057
KEGG
MeSH Oxindole
PubChem CID
RTECS number
  • NM2080500
UNII
  • InChI=1S/C8H7NO/c10-8-5-6-3-1-2-4-7(6)9-8/h1-4H,5H2,(H,9,10) Yes check.svgY
    Key: JYGFTBXVXVMTGB-UHFFFAOYSA-N Yes check.svgY
  • c1ccc2c(c1)CC(=O)N2
Properties
C8H7NO
Molar mass 133.150 g·mol−1
Appearancepale yellow solid
Melting point 128 °C (262 °F; 401 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Oxindole (2-indolone) is an aromatic heterocyclic organic compound with the formula C6H4CHC(O)NH. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing ring. Oxindole is a modified indoline with a substituted carbonyl at the second position of the 5-member indoline ring. Classified as a cyclic amide, it is a pale yellow solid.

Contents

Formation and reactions

Oxindole is derived in nature from tryptophan, 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 with hepatic encephalopathy have been recorded to have elevated serum oxindole levels. [1]

Treatment with phosphorus pentasulfide gives the thione.

Oxindoles

Rhynchophylline, a naturally occurring oxindole is a medicinal used as an NMDA antagonist and a calcium channel blocker. Rhynchophylline.svg
Rhynchophylline, a naturally occurring oxindole is a medicinal used as an NMDA antagonist and a calcium channel blocker.

Beyond, the parent compound, oxindoles include many compounds. [3] One example is 3-methyloxindole. [4]

Related Research Articles

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References

  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 in Xenopus Oocytes". 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.