Oxindole

From Wikipedia, the free encyclopedia
(Redirected from Oxindol)
Jump to navigation Jump to search

<templatestyles src="Chembox/styles.css"/>

Template:Chembox image cellTemplate:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox Datapage checkTemplate:Chembox Footer
Oxindole
Template:Longitem Template:Unbulleted list
Template:Longitem 114692
ChEBI Template:Unbulleted list
ChemSpider Template:Unbulleted list
DrugBank Template:Unbulleted list
EC Number Template:Unbulleted list
Template:Longitem 637057
KEGG Template:Unbulleted list
MeSH Oxindole
Template:Longitem Template:Unbulleted list
RTECS number Template:Unbulleted list
Script error: No such module "collapsible list".
Script error: No such module "collapsible list".
Template:Longitem Template:Chembox Elements/molecular formula
Molar mass Template:Chem molar mass
Appearance pale yellow solid
Melting point Template:Chembox CalcTemperatures

Template:Chembox Footer/trackingScript error: No such module "TemplatePar".Template:Short description

Oxindole (2-indolone) is an aromatic heterocyclic organic compound with the formula Template:Chem2. 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

Beyond the parent compound, the oxindole structure is present in many compounds[2] including, for example, rhynchophylline, 3-methyloxindole,[3] and semaxanib.[4]

File:Rhynchophylline.svg
Rhynchophylline, a naturally occurring oxindole is a medicinal used as an NMDA antagonist and a calcium channel blocker.[5]

References

<templatestyles src="Reflist/styles.css" />

  1. Script error: No such module "Citation/CS1".
  2. Script error: No such module "Citation/CS1".
  3. Script error: No such module "Citation/CS1".
  4. Script error: No such module "Citation/CS1".
  5. Script error: No such module "Citation/CS1".

Script error: No such module "Check for unknown parameters".