Synthesis and cytotoxic activity of geranylmethoxyhydroquinone derivatives

• Evelyn Baeza Maturana ^[3] ; Karen Catalán Marín ^[3] ; Joan Villena García ^[1] ; Héctor Carrasco Altamirano ^[2] ; Mauricio Cuellar Fritis ^[1] ; Luis Espinoza Catalán ^[3]
  1. [1] Universidad de Valparaíso

     Universidad de Valparaíso

     Valparaíso, Chile

     
  2. [2] Universidad Andrés Bello

     Universidad Andrés Bello

     Santiago, Chile

     
  3. [3] Universidad Técnica Federico Santa María Departamento de Química

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• Localización: Journal of the Chilean Chemical Society (Boletín de la Sociedad Chilena de Química), ISSN-e 0717-6309, ISSN 0366-1644, Vol. 57, Nº. 3, 2012, págs. 1219-1223
• Idioma: inglés
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• Resumen

  • The new synthetic geranyl-2,4-methoxyhydroquinone 1 and the known geranyl-4,5-methoxyhydroquinone 2 were prepared by Electrophilic Aromatic Substitution (EAS) reactions between geraniol and 1,3,5-trimethoxyphenol using BF3·Et2O as a catalyst. Furthermore, the new geranylmethoxyhydroquinones derivatives (3-6) were obtained by chemical transformations of 1 and 2. The compounds have been evaluated for their cytotoxic activities against PC-3 human prostate cancer cell line, MCF-7 and MDA-MB-231 human breast cancer cells lines and dermal human fibroblasts DHF. IC50 values for compounds 1 and 5 ranged in the 80 µM level.