Hamayne

Hamayne is an alkaloid present in plants of the family Amaryllidaceae, including Iberian Narcissus species and two Nigerian Crinum species, reported to have acetylcholinesterase inhibitory activity.[1] The product has been made via total synthesis as well.[2]

Hamayne
Names
Systematic IUPAC name
(3α,11R,13β)-1,2-Didehydrocrinan-3,11-diol
Other names
Bulbispermine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
  • InChI=1S/C16H17NO4/c18-10-1-2-16-11-5-13-12(20-8-21-13)3-9(11)6-17(7-15(16)19)14(16)4-10/h1-3,5,10,14-15,18-19H,4,6-8H2/t10-,14-,15-,16+/m0/s1
    Key: KWAOMPWGIIXDPH-BLQKSXIESA-N
  • InChI=1/C16H17NO4/c18-10-1-2-16-11-5-13-12(20-8-21-13)3-9(11)6-17(7-15(16)19)14(16)4-10/h1-3,5,10,14-15,18-19H,4,6-8H2/t10-,14-,15-,16+/m0/s1
    Key: KWAOMPWGIIXDPH-BLQKSXIEBO
  • C1[C@H](C=C[C@@]23[C@H]1N(C[C@@H]2O)CC4=CC5=C(C=C34)OCO5)O
Properties
C16H17NO4
Molar mass 287.315 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

References
  1. López, Susana; Bastida, Jaume; Viladomat, Francesc; Codina, Carles (2002). "Acetylcholinesterase inhibitory activity of some Amaryllidaceae alkaloids and Narcissus extracts". Life Sciences. 71 (21): 2521–2529. doi:10.1016/S0024-3205(02)02034-9. PMID 12270757.
  2. Petit, Laurent; Banwell, Martin G.; Willis, Anthony C. (2011). "The Total Synthesis of the Crinine Alkaloid Hamayne via a Pd[0]-Catalyzed Intramolecular Alder-Ene Reaction". Organic Letters. 13 (21): 5800–5803. doi:10.1021/ol2023938. PMID 21970722.


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