Hamayne

Hamayne
Names
Systematic IUPAC name
(3α,11R,13β)-1,2-Didehydrocrinan-3,11-diol
Other names
Bulbispermine
Identifiers
CAS Number
  • 61948-11-6 ☒N[EPA]
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:31667
ChEMBL
  • ChEMBL3916492
ChemSpider
  • 23327027
KEGG
  • C12164
PubChem CID
  • 443670
CompTox Dashboard (EPA)
  • DTXSID90332125
InChI
  • 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
Chemical formula
 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
Chemical compound

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]

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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