Horsfiline
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| Horsfiline | |
|---|---|
| File:Horsfiline.png | |
| (3R)-5-methoxy-1'-methylspiro[1H-indole-3,3'-pyrrolidine]-2-one | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 136247-72-8 |
| PubChem | 11042617 |
| SMILES | Script error: No such module "collapsible list". |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | C13H16N2O2 |
| Molar mass | 232.278 |
| Melting point |
125-126 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Horsfiline is an oxindole alkaloid found in the plant Horsfieldia superba,[1] which is used in traditional herbal medicine. It has analgesic effects and has been the subject of significant research both to produce it synthetically by convenient routes,[2][3][4][5] and to develop analogues and derivatives which may have improved analgesic effects.[6][7]
References
- ↑ Jossang A, Jossang P, Hadi HA, Sevenet T, Bodo B. Horsfiline, an oxindole alkaloid from Horsfieldia superba. Journal of Organic Chemistry 1991; 56(23):6527-6530. DOI 10.1021/jo00023a016
- ↑ Lakshmaiah G, Kawabata T, Shang M, Fuji K. Total Synthesis of (-)-Horsfiline via Asymmetric Nitroolefination. Journal of Organic Chemistry. 1999 Mar 5;64(5):1699-1704. PMID 11674239
- ↑ Cravotto G, Giovenzana GB, Pilati T, Sisti M, Palmisano G. Azomethine ylide cycloaddition/reductive heterocyclization approach to oxindole alkaloids: asymmetric synthesis of (-)-horsfiline. Journal of Organic Chemistry. 2001 Dec 14;66(25):8447-53. PMID 11735524
- ↑ Murphy JA, Tripoli R, Khan TA, Mali UW. Novel phosphorus radical-based routes to horsfiline. Organic Letters. 2005 Jul 21;7(15):3287-9. PMID 16018642
- ↑ Trost BM, Brennan MK. Palladium asymmetric allylic alkylation of prochiral nucleophiles: horsfiline. Organic Letters. 2006 May 11;8(10):2027-30. PMID 16671773
- ↑ Tsai YC, Liou JP, Liao R, Cheng CY, Tao PL. C-alkylated spiro[benzofuran-3(2H),4'-1'-methyl-piperidine-7-ols] as potent opioids: a conformation-activity study. Bioorganic and Medicinal Chemistry Letters. 1998 Jul 21;8(14):1813-8. PMID 9873439
- ↑ Alf Claesson, Britt-Marie Swahn, Odd-Geir Berge. Spirooxindole derivatives that act as analgesics. US Patent 6774132
