Oxindole

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Oxindole
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Oxindole
Systematic IUPAC name
2,3-Dihydro-1H-indol-2-one
Identifiers
59-48-3 YesY
3DMet B04450
114692
ChEBI CHEBI:31697 YesY
ChEMBL ChEMBL40823 YesY
ChemSpider 284794 YesY
EC number 200-429-5
637057
Jmol-3D images Image
KEGG C12312 N
MeSH Oxindole
PubChem 321710
RTECS number NM2080500
Properties
C8H7NO
Molar mass 133.15 g·mol−1
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).
 N verify (what isYesY/N?)
Infobox references

Oxindole (2-indolone) is an aromatic heterocyclic organic compound. 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.

Oxindole is a tryptophan derivative and in human biology is 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] Recently, oxindoles, as the anticancer agents, have drawn wide attention.[2] Among them, CFI-400945 has advanced into phase 1 clinical trials for cancer therapy as the first PLK4 inhibitor, albeit with the possible problem on kinase selectivity.[3] An interesting finding is that steroid-oxindole hybrids have shown excellent cytotoxicity against human cancer cell lines and can inhibit cell cycle and induce cell apoptosis.[4][5]

Related aromatic compounds[edit]

Precursor[edit]

Oxindole is used as a precursor in the synthesis of Amfenac, ..

References[edit]

  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. 
  2. ^ "Spirooxindoles: Promising scaffolds for anticancer agents". www.sciencedirect.com. Retrieved 2015-06-13. 
  3. ^ "Discovery of orally active anticancer candidate CFI-400945 derived from biologically promising spirooxindoles: Success and challenges". www.sciencedirect.com. Retrieved 2015-06-13. 
  4. ^ "Design, synthesis and biological evaluation of novel steroidal spiro-oxindoles as potent antiproliferative agents". www.sciencedirect.com. Retrieved 2015-06-13. 
  5. ^ "Discovery of novel steroidal pyran–oxindole hybrids as cytotoxic agents". www.sciencedirect.com. Retrieved 2015-06-13.