Oxindole

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Oxindole
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
1,3-Dihydro-2H-indol-2-one
Identifiers
3D model (JSmol)
114692
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.390 Edit this at Wikidata
EC Number
  • 200-429-5
637057
KEGG
MeSH Oxindole
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) checkY
    Key: JYGFTBXVXVMTGB-UHFFFAOYSA-N checkY
  • c1ccc2c(c1)CC(=O)N2
Properties
C8H7NO
Molar mass 133.150 g·mol−1
Appearance pale 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).

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.

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.[2]

Beyond the parent compound, the oxindole structure is present in many compounds,[3] for example 3-methyloxindole[4] and semaxanib.[5]

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.
  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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