Horsfiline

Horsfiline
Names
Preferred IUPAC name
(3R)-5-Methoxy-1′-methylspiro[indole-3,3′-pyrrolidin]-2(1H)-one
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C13H16N2O2/c1-15-6-5-13(8-15)10-7-9(17-2)3-4-11(10)14-12(13)16/h3-4,7H,5-6,8H2,1-2H3,(H,14,16)/t13-/m0/s1 checkY
    Key: RVOLLKGLJIUGLG-ZDUSSCGKSA-N checkY
  • InChI=1/C13H16N2O2/c1-15-6-5-13(8-15)10-7-9(17-2)3-4-11(10)14-12(13)16/h3-4,7H,5-6,8H2,1-2H3,(H,14,16)/t13-/m0/s1
    Key: RVOLLKGLJIUGLG-ZDUSSCGKBT
  • O=C2Nc1c(cc(OC)cc1)[C@]23CN(C)CC3
Properties
C13H16N2O2
Molar mass 232.283 g·mol−1
Melting point 125 to 126 °C (257 to 259 °F; 398 to 399 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Horsfiline is an oxindole alkaloid found in the plant Horsfieldia superba,[1] which is used in traditional herbal medicine. It has analgesic effects[medical citation needed] and has been the subject of research both to produce it synthetically by convenient routes[2][3][4][5][6][7][8] and to develop analogues and derivatives which may have improved analgesic effects.[9][10]

It is a member of the spiroindolone class. Elacomine has a similar chemical structure.

References

[edit]
  1. ^ Jossang A, Jossang P, Hadi HA, Sevenet T, 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 (March 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 (December 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 (July 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 (May 2006). "Palladium asymmetric allylic alkylation of prochiral nucleophiles: horsfiline". Organic Letters. 8 (10): 2027–30. doi:10.1021/ol060298j. PMC 2565574. PMID 16671773.
  6. ^ Hong S, Jung M, Park Y, Ha MW, Park C, Lee M, Park HG (July 2013). "Efficient enantioselective total synthesis of (-)-horsfiline". Chemistry: A European Journal. 19 (29): 9599–605. doi:10.1002/chem.201301008. PMID 23836402.
  7. ^ Mukaiyama T, Ogata K, Sato I, Hayashi Y (October 2014). "Asymmetric organocatalyzed Michael addition of nitromethane to a 2-oxoindoline-3-ylidene acetaldehyde and the three one-pot sequential synthesis of (-)-horsfiline and (-)-coerulescine". Chemistry: A European Journal. 20 (42): 13583–8. doi:10.1002/chem.201403932. PMID 25155110.
  8. ^ Buev EM, Moshkin VS, Sosnovskikh VY (December 2017). "Nonstabilized Azomethine Ylides in the Mannich Reaction: Synthesis of 3,3-Disubstituted Pyrrolidines, Including Oxindole Alkaloids". The Journal of Organic Chemistry. 82 (23): 12827–12833. doi:10.1021/acs.joc.7b02193. PMID 29048900.
  9. ^ Tsai YC, Liou JP, Liao R, Cheng CY, Tao PL (July 1998). "C-alkylated spiro[benzofuran-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.
  10. ^ Alf Claesson, Britt-Marie Swahn, Odd-Geir Berge. Spirooxindole derivatives that act as analgesics. US Patent 6774132
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