Horsfiline

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ImageFile=Horsfiline.pngImageSize=250px
IUPACName=(3R)-5-methoxy-1'-methylspiro [1H-indole-3,3'-pyrrolidine] -2-one
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PubChem=11042617
SMILES=CN1CC [C@] 2(C1)C3=C(C=CC(=C3)OC)NC2=O
Section2= Chembox Properties
Formula=C₁₃H₁₆N₂O₂
MolarMass=232.278
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MeltingPt=125-126 °C
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Horsfiline is an oxindole alkaloid found in the plant "Horsfieldia superba", [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] 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, [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] and to develop analogues and derivatives which may have improved analgesic effects. [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] [ [http://www.google.com/patents?id=4ooRAAAAEBAJ&dq=6774132 Alf Claesson, Britt-Marie Swahn, Odd-Geir Berge. Spirooxindole derivatives that act as analgesics. US Patent 6774132] ]

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