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Molecules 2010, 15(9), 6502-6511; doi:10.3390/molecules15096502
Article

Synthesis and Antitumor Activity of Diterpenylhydroquinone Derivatives of Natural Ent-Labdanes

1,* , 1,3, 1, 1, 2, 3 and 4,*
1 Departamento de Química, Universidad Técnica Federico Santa María, Av. España N 1680, Valparaíso, Chile 2 Departamento de Ciencias Químicas, Universidad Andrés Bello, Campus Viña del Mar, Los Fresnos N 52, Viña del Mar, Chile 3 Facultad de Farmacia, Universidad de Valparaíso, Av. Gran Bretaña N 1093, Valparaíso, Chile 4 Facultad de Medicina, Universidad de Valparaíso, Av. Hontaneda N 2664, Centro Regional de Estudios en Alimentos Saludables (CREAS), Valparaíso, Chile
* Authors to whom correspondence should be addressed.
Received: 28 August 2010 / Revised: 8 September 2010 / Accepted: 15 September 2010 / Published: 17 September 2010
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Abstract

Two new compounds 2β-acetoxy-15-phenyl-(22,25-acetoxy)-ent-labda-8(17), 13(E)-diene (9) and 2β-hydroxy-15-phenyl-(22,24,26-trimethoxy)-ent-labda-8(17),13(E)-diene (10) have been prepared by an Electrophilic Aromatic Substitution (EAS) reaction between diterpenyl allylic alcohols and 1,4-hydroquinone or 1,3,5-trimethoxybenzene using BF3.Et2O as a catalyst. These compounds, along with a series of natural ent-labdanes 3-8, have been evaluated for their in vitro cytotoxic activities against cultured human cancer cells of PC-3 and DU-145 human prostate cancer, MCF-7 and MDA-MB-231 breast carcinoma and dermal human fibroblasts (DHF). Some compounds displayed inhibition at µM IC50 values.
Keywords: diterpenylhydroquinones; ent-labdanes; antitumoral activity diterpenylhydroquinones; ent-labdanes; antitumoral activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Catalán, L.E.; Maturana, E.B.; Marín, K.C.; Olivares, M.O.; Altamirano, H.C.; Fritis, M.C.; García, J.V. Synthesis and Antitumor Activity of Diterpenylhydroquinone Derivatives of Natural Ent-Labdanes. Molecules 2010, 15, 6502-6511.

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