Horsfiline

Horsfiline
IUPAC name

(3R)-5-methoxy-1'-methylspiro[1H-indole-3,3'-pyrrolidine]-2-one
Identifiers
CAS number 136247-72-8 Y
PubChem 11042617
ChemSpider 9217785 Y
Jmol-3D images Image 1
Properties
Molecular formula C13H16N2O2
Molar mass 232.278
Melting point

125-126 °C
 Y (verify) (what is: Y/N?)
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

  1. ^ Jossang, A; Jossang, P; Hadi, HA; Sevenet, T; Horsfiline, Bodo B. (1991). "An oxindole alkaloid from Horsfieldia superba". Journal of Organic Chemistry 56 (23): 6527–6530. doi:10.1021/jo00023a016. 
  2. ^ Lakshmaiah, G; Kawabata, T; Shang, M; Fuji, K (1999). "Total Synthesis of (-)-Horsfiline via Asymmetric Nitroolefination.". The Journal of organic chemistry 64 (5): 1699–1704. doi:10.1021/jo981577q. PMID 11674239. 
  3. ^ Cravotto, G; Giovenzana, GB; Pilati, T; Sisti, M; Palmisano, G (2001). "Azomethine ylide cycloaddition/reductive heterocyclization approach to oxindole alkaloids: asymmetric synthesis of (-)-horsfiline.". The Journal of organic chemistry 66 (25): 8447–53. doi:10.1021/jo015854w. PMID 11735524. 
  4. ^ Murphy, JA; Tripoli, R; Khan, TA; Mali, UW (2005). "Novel phosphorus radical-based routes to horsfiline.". Organic letters 7 (15): 3287–9. doi:10.1021/ol051095i. PMID 16018642. 
  5. ^ Trost, BM; Brennan, MK (2006). "Palladium Asymmetric Allylic Alkylation of Prochiral Nucleophiles: Horsfiline". Organic letters 8 (10): 2027–30. doi:10.1021/ol060298j. PMC 2565574. PMID 16671773. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2565574. 
  6. ^ Tsai, YC; Liou, JP; Liao, R; Cheng, CY; Tao, PL (1998). "C-alkylated spirobenzofuran-3(2H),4'-1'-methyl-piperidine-7-ols as potent opioids: a conformation-activity study". Bioorganic & medicinal chemistry letters 8 (14): 1813–8. doi:10.1016/S0960-894X(98)00318-7. PMID 9873439. 
  7. ^ Alf Claesson, Britt-Marie Swahn, Odd-Geir Berge. Spirooxindole derivatives that act as analgesics. US Patent 6774132