Horsfiline

Horsfiline
Names
	IUPAC name (3R)-5-methoxy-1'-methylspiro[1H-indole-3,3'-pyrrolidine]-2-one
Identifiers
CAS Number	136247-72-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	9217785 ;
PubChem CID	11042617;
CompTox Dashboard (EPA)	DTXSID40453071 ;
	InChI 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 Key: RVOLLKGLJIUGLG-ZDUSSCGKSA-N ; 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;
	SMILES O=C2Nc1c(cc(OC)cc1)[C@]23CN(C)CC3;
Properties
Chemical formula	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).
	verify (what is ?)
	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 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]

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

References

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.
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.
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.
Alf Claesson, Britt-Marie Swahn, Odd-Geir Berge. Spirooxindole derivatives that act as analgesics. US Patent 6774132

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[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] 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.

[7] Alf Claesson, Britt-Marie Swahn, Odd-Geir Berge. Spirooxindole derivatives that act as analgesics. US Patent 6774132