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Affinisine

Affinisine
Affinisine.svg
Names
IUPAC name
((6S,7R,10R,11R,11aS,E)-9-ethylidene-5-methyl-5,6,8,9,10,11,11a,12-octahydro-6,10-methanoindolo[3,2-b]quinolizin-11-yl)methanol
Other names
1-Methylsarpagan-17-ol, De(hydroxymethyl)voachalotinol
Identifiers
3D model (JSmol)
ChemSpider
Properties
C20H24N2O
Molar mass 308.43 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

Affinisine is a monoterpenoid indole alkaloid which can be isolated from plants of the genus Tabernaemontana.[1][2] Structurally it can be considered a member of the sarpagine alkaloid family and may be synthesized from tryptophan via a Pictet-Spengler reaction.[3][4] Limited pharmacological testing has indicated that it may be an effective inhibitor of both acetylcholinesterase and butyrylcholinesterase.[1][5]

See also

References

  1. ^ a b Andrade, Marcelo T.; Lima, Josélia A.; Pinto, Angelo C.; Rezende, Claudia M.; Carvalho, Meriane P.; Epifanio, Rosângela A. (June 2005). "Indole alkaloids from Tabernaemontana australis (Müell. Arg) Miers that inhibit acetylcholinesterase enzyme". Bioorganic & Medicinal Chemistry. 13 (12): 4092–4095. doi:10.1016/j.bmc.2005.03.045. PMID 15911323.
  2. ^ Clivio, Pascale; Richard, Bernard; Deverre, Jean-Robert; Sevenet, Thierry; Zeches, Monique; Le Men-Oliver, Louisette (January 1991). "Alkaloids from leaves and root bark ofErvatamia hirta". Phytochemistry. 30 (11): 3785–3792. doi:10.1016/0031-9422(91)80111-D.
  3. ^ Liu, Xiaoxiang; Wang, Tao; Xu, Qingge; Ma, Chunrong; Cook, James M (August 2000). "Enantiospecific total synthesis of the enantiomer of the indole alkaloid affinisine". Tetrahedron Letters. 41 (33): 6299–6303. doi:10.1016/S0040-4039(00)01061-3.
  4. ^ Liao, Xuebin; Zhou, Hao; Yu, Jianming; Cook, James M. (November 2006). "An Improved Total Synthesis of (+)-Macroline and Alstonerine as Well as the Formal Total Synthesis of (−)-Talcarpine and (−)-Anhydromacrosalhine−methine". The Journal of Organic Chemistry. 71 (23): 8884–8890. doi:10.1021/jo061652u. PMID 17081019.
  5. ^ Vieira, Ivo J.C.; Medeiros, Walter L.B.; Monnerat, Cecilia S.; Souza, Jucimar J.; Mathias, Leda; Braz-Filho, Raimundo; Pinto, Angelo C.; Sousa, Priscila M.; Rezende, Claudia M.; Epifanio, Rosângela De A. (September 2008). "Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures". Anais da Academia Brasileira de Ciências. 80 (3): 419–426. doi:10.1590/S0001-37652008000300003.