Synthesis and conformational analysis of leptocarpin derivatives. Influence of modification of the oxirane ringon leptocarpin's cytotoxic activity

Rolando Martínez, Victor Kesternich, Héctor Carracso, Carolina Álvarez-Contreras, Carolina Montenegro, Ricardo Ugarte, Elena Gutiérrez, José Moreno, Carlos García, Enrique Werner, Juan Cárcamos

Resultado de la investigación: Contribución a una revistaArtículo

6 Citas (Scopus)

Resumen

The reaction in acidconditions of Leptocarpin 1, a compound with antitumor activity, formed two new isomeric products, 8β-angeloyl-1β,3β- dihydroxy-4,10-dimethyl,-Δ11(13) methylen-4Z,9Z-dieneheliangol- 6,12-olide 2 and 8β-angeloyl-1β,3β-dihydroxy-4-methyl- Δ11(13)11(14)-dimethylen-4Z-eneheliangol-6, 12-olide 3, whose structures reported in this study were established by spectroscopy (1H-NMR, 13C-NMR, MS and IR) and confirmedthrough ROESY experiments and theoretical studies by molecular mechanics. The in vitro cytotoxicity of these isomeric compounds was less active than leptocarpin, showing the importance of the oxirane ring in the biological activity. Cytotoxic activity was measured in six cancer cell lines.

Idioma originalInglés
Páginas (desde-hasta)1010-1014
Número de páginas5
PublicaciónJournal of the Chilean Chemical Society
Volumen51
N.º4
DOI
EstadoPublicada - dic 2006

Áreas temáticas de ASJC Scopus

  • Química (todo)

Huella Profundice en los temas de investigación de 'Synthesis and conformational analysis of leptocarpin derivatives. Influence of modification of the oxirane ringon leptocarpin's cytotoxic activity'. En conjunto forman una huella única.

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    Martínez, R., Kesternich, V., Carracso, H., Álvarez-Contreras, C., Montenegro, C., Ugarte, R., Gutiérrez, E., Moreno, J., García, C., Werner, E., & Cárcamos, J. (2006). Synthesis and conformational analysis of leptocarpin derivatives. Influence of modification of the oxirane ringon leptocarpin's cytotoxic activity. Journal of the Chilean Chemical Society, 51(4), 1010-1014. https://doi.org/10.4067/S0717-97072006000400003