Kopsanone

Kopsanone is an alkaloid isolated from Aspidosperma.[1]

Kopsanone
Names
IUPAC name
5,14-diazaheptacyclo[12.5.3.01,13.04,12.04,18.06,11.012,16]docosa-6,8,10-trien-17-one
Other names
Kopsan-22-one
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C20H22N2O/c23-16-13-10-18-6-3-9-22-11-14(16)20(17(18)22)12-4-1-2-5-15(12)21-19(13,20)8-7-18/h1-2,4-5,13-14,17,21H,3,6-11H2
    Key: RFDVSXYPLPEIGZ-UHFFFAOYSA-N
  • C1CC23CCC45C(C2)C(=O)C6C4(C3N(C1)C6)C7=CC=CC=C7N5
Properties
C20H22N2O
Molar mass 306.409 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. Mitaine, AC; Mesbah, K; Richard, B; Petermann, C; Arrazola, S; Moretti, C; Zèches-Hanrot, M; Men-Olivier, LL (1996). "Alkaloids from Aspidosperma species from Bolivia". Planta Med. 62 (5): 458–61. doi:10.1055/s-2006-957939. PMID 17252481.

Extra reading
  • Klein-Júnior, Lc; Bannwart, G; Kato, L; Oliveira, Cma; Gontijo, B; Silva, Cc; Ferreira, Hd; Vander Heyden, Y; Passos, Cs; Henriques, At; Santin, Smo (25 November 2015). "Kopsanone and N(4)-oxide-kopsanone: two β-carbolinic indole alkaloids with monoamine oxidase A inhibitory activity". Planta Medica. 81 (16): s–0035–1565743. doi:10.1055/s-0035-1565743.
  • Craven, B. M. (1 October 1969). "The crystal structure and absolute configuration of the N ( b )-methiodide of (−)-kopsanone". Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry. 25 (10): 2131–2139. doi:10.1107/S0567740869005243.
  • Leng, Lingying; Zhou, Xiaohan; Liao, Qi; Wang, Falu; Song, Hao; Zhang, Dan; Liu, Xiao-Yu; Qin, Yong (20 March 2017). "Asymmetric Total Syntheses of Kopsia Indole Alkaloids". Angewandte Chemie International Edition. 56 (13): 3703–3707. doi:10.1002/anie.201700831.
  • Layne, Tanya H.; Roach, Joy S.; Tinto, Winston F. (January 2015). "Review of β-carboline Alkaloids from the Genus Aspidosperma". Natural Product Communications. 10 (1): 1934578X1501000. doi:10.1177/1934578X1501000139.open access


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