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Isovoacangine

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Isovoacangine
Identifiers
  • methyl 17-ethyl-6-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC22H28N2O3
Molar mass368.477 g·mol−1
3D model (JSmol)
  • CCC1CC2CC3(C1N(C2)CCc4c3[nH]c5c4ccc(c5)OC)C(=O)OC
  • InChI=1S/C22H28N2O3/c1-4-14-9-13-11-22(21(25)27-3)19-17(7-8-24(12-13)20(14)22)16-6-5-15(26-2)10-18(16)23-19/h5-6,10,13-14,20,23H,4,7-9,11-12H2,1-3H3
  • Key:FPUHKQMDWMVBRI-UHFFFAOYSA-N

Isovoacangine is a naturally occurring substance related to voacangine. It showed negative chronotropic and negative inotropic activity.[1]

Chemistry

Synthesis

Derivatives

3-Hydroxyisovoacangine and 3-(2'-oxopropyl)isovoacangine are derivates of isovoacangine.[2]

Natural occurrence

It occurs naturally in many Tabernaemontana (milkwood) species such as Tabernaemontana pachysiphon and Tabernaemontana_divaricata.[3][4]

See also

References

  1. ^ Pratchayasakul W, Pongchaidecha A, Chattipakorn N, Chattipakorn S (April 2008). "Ethnobotany & ethnopharmacology of Tabernaemontana divaricata" (PDF). The Indian Journal of Medical Research. 127 (4): 317–35. PMID 18577786. S2CID 1119874.
  2. ^ Danieli B, Palmisano G (January 1987). "Alkaloids from Tabernaemontana.". In Brossi A (ed.). The alkaloids: Chemistry and Pharmacology. Vol. 27. Academic Press. pp. 1–130 (82). ISBN 978-0-08-086551-5.
  3. ^ "Tabernaemontana undulata - Useful Tropical Plants". tropical.theferns.info.
  4. ^ Kam TS, Loh KY, Wei C (November 1993). "Conophylline and conophyllidine: new dimeric alkaloids from Tabernaemontana divaricata". Journal of Natural Products. 56 (11): 1865–71. doi:10.1021/np50101a001.