Elacomine

Elacomine
Names
	IUPAC name (2'S,3R)-6-hydroxy-2'-(2-methylpropyl)spiro[1H-indole-3,3'-pyrrolidine]-2-one
Identifiers
CAS Number	176300-92-8;
3D model (JSmol)	Interactive image;
ChemSpider	9164226;
PubChem CID	10989031;
	InChI InChI=1S/C15H20N2O2/c1-9(2)7-13-15(5-6-16-13)11-4-3-10(18)8-12(11)17-14(15)19/h3-4,8-9,13,16,18H,5-7H2,1-2H3,(H,17,19)/t13-,15+/m0/s1 Key: HBHCBIIRYVIJGE-DZGCQCFKSA-N;
	SMILES CC(C)C[C@H]1[C@@]2(CCN1)C3=C(C=C(C=C3)O)NC2=O;
Properties
Chemical formula	C15H20N2O2
Molar mass	260.337 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Elacomine is a natural oxindole alkaloid found in the plant species Elaeagnus commutata.^[1]

Synthethic routes for obtaining this compound have been described, based on 2-halotryptamines.^[1] Different approaches, such as regiospecific synthesis, were also mentioned.^[2]

It is a member of the spiroindolone class (specifically, a spirooxindolopyrrolizidine derivative). Horsfiline has a similar chemical structure.

References

^ ^a ^b Miyake, FY, Yakushijin, K, Horne, DA (2004). "Preparation and Synthetic Applications of 2-Halotryptamines: Synthesis of Elacomine and Isoelacomine". Organic Letters. 6 (5): 711–713. doi:10.1021/ol030138x.
^ Thangamani A (2010). "Regiospecific synthesis and biological evaluation of spirooxindolopyrrolizidines via [3+2] cycloaddition of azomethine ylide". European Journal of Medicinal Chemistry. 45 (12): 6120–6126. doi:10.1016/j.ejmech.2010.09.051. PMID 20947223.

[Miyake-1] Miyake, FY, Yakushijin, K, Horne, DA (2004). "Preparation and Synthetic Applications of 2-Halotryptamines: Synthesis of Elacomine and Isoelacomine". Organic Letters. 6 (5): 711–713. doi:10.1021/ol030138x.

[2] Thangamani A (2010). "Regiospecific synthesis and biological evaluation of spirooxindolopyrrolizidines via [3+2] cycloaddition of azomethine ylide". European Journal of Medicinal Chemistry. 45 (12): 6120–6126. doi:10.1016/j.ejmech.2010.09.051. PMID 20947223.

[1]

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