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]
Quick Facts Names, Identifiers ...
Horsfiline
|
Names |
Preferred IUPAC name
(3R)-5-Methoxy-1′-methylspiro[indole-3,3′-pyrrolidin]-2(1H)-one |
Identifiers |
|
|
|
|
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 YKey: RVOLLKGLJIUGLG-ZDUSSCGKSA-N YInChI=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).
|
Close
It is a member of the spiroindolone class. Elacomine has a similar chemical structure.
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.
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.
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.
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.
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.
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.