Synthesis and conformational analysis of leptocarpin derivatives: Influence of modification of the oxirane ringon leptocarpin'S cytotoxic activity

• ROLANDO MARTÍNEZ ^[1] ; VICTOR KESTERNICH ^[2] ; HÉCTOR CARRACSO ^[3] ; CAROLINA ÁLVAREZ-CONTRERAS ^[1] ; CAROLINA MONTENEGRO ^[1] ; RICARDO UGARTE ^[1] ; ELENA GUTIÉRREZ ^[1] ; JOSÉ MORENO ^[1] ; CARLOS GARCÍA ^[1] ; ENRIQUE WERNER ^[1] ; JUAN CÁRCAMOS ^[1]
  1. [1] Universidad Austral de Chile

     Universidad Austral de Chile

     Valdivia, Chile

     
  2. [2] Universidad Católica del Norte

     Universidad Católica del Norte

     Antofagasta, Chile

     
  3. [3] Universidad Andrés Bello

     Universidad Andrés Bello

     Santiago, Chile

     

  Mostrar afiliaciones +
• Localización: Journal of the Chilean Chemical Society (Boletín de la Sociedad Chilena de Química), ISSN-e 0717-6309, ISSN 0366-1644, Vol. 51, Nº. 4, 2006, págs. 1010-1014
• Idioma: inglés
• Enlaces
  • Texto completo
• Resumen

  • The reaction in acidconditions of Leptocarpin 1, a compound with antitumor activity, formed two new isomeric products, 8b-angeloyl-1b,3b-dihydroxy-4,10-dimethyl,-D11(13) methylen-4Z,9Z-dieneheliangol-6,12-olide 2 and 8b-angeloyl-1b,3b-dihydroxy-4-methyl-D11(13),D11(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