![]() | |
![]() | |
Names | |
---|---|
Preferred IUPAC name
1,3-Dihydro-2H-indol-2-one | |
Identifiers | |
3D model (JSmol)
|
|
114692 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.000.390 |
EC Number |
|
637057 | |
KEGG | |
MeSH | Oxindole |
PubChem CID
|
|
RTECS number |
|
UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
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
[edit]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
[edit]![](Https://upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Rhynchophylline.svg/220px-Rhynchophylline.svg.png)
Beyond, the parent compound, oxindoles include many compounds,[3] for example 3-methyloxindole[4] and semaxanib.[5]
References
[edit]- ^ 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 in Xenopus Oocytes". 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.
Well, that’s interesting to know that Psilotum nudum are known as whisk ferns. Psilotum nudum is the commoner species of the two. While the P. flaccidum is a rare species and is found in the tropical islands. Both the species are usually epiphytic in habit and grow upon tree ferns. These species may also be terrestrial and grow in humus or in the crevices of the rocks.
View the detailed Guide of Psilotum nudum: Detailed Study Of Psilotum Nudum (Whisk Fern), Classification, Anatomy, Reproduction