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Molecules 2011, 16(6), 4632-4641; doi:10.3390/molecules16064632

New Catechol Derivatives of Safrole and Their Antiproliferative Activity towards Breast Cancer Cells

1
Departamento de Química, Universidad Técnica Federico Santa María, Av. España N° 1680, Valparaíso, Chile
2
Centro de Investigaciones Biomedicas (CIB), Centro Regional de Estudios en Alimentos Saludables, Escuela de Medicina, Universidad de Valparaíso, Creas, Av. Hontaneda N° 2664, Valparaíso, Chile
3
Departamento de Ciencias Químicas, Universidad Andrés Bello, Campus Viña del Mar, Los Fresnos N° 52, Viña del Mar, Chile
*
Authors to whom correspondence should be addressed.
Received: 13 April 2011 / Revised: 31 May 2011 / Accepted: 2 June 2011 / Published: 3 June 2011
(This article belongs to the Section Organic Synthesis)
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Abstract

Catechols were synthesized from safrole. Nine derivatives were prepared and assessed for antiproliferative effects using different human cell lines. The in vitro growth inhibition assay was based on the sulphorhodamine dye to quantify cell viability. The derivatives 4-allylbenzene-1,2-diol (3), 4 4-[3-(acetyloxy)propyl]-1,2-phenylene diacetate (6) and 4-[3-(acetyloxy)propyl]-5-nitro-1,2-phenylene diacetate (10) showed higher cytotoxicity than the parent compound 2 in tests performed on two breast cancer cell lines (MCF-7 and MDA-MB-231). The IC50 values of 40.2 ± 6.9 μM, 5.9 ± 0.8 μM and 33.8 ± 4.9 μM, respectively, were obtained without toxicity towards dermal human fibroblast (DHF cells).
Keywords: antiproliferative activity; catechol; synthesis antiproliferative activity; catechol; synthesis
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Madrid Villegas, A.; Espinoza Catalán, L.; Montenegro Venegas, I.; Villena García, J.; Carrasco Altamirano, H. New Catechol Derivatives of Safrole and Their Antiproliferative Activity towards Breast Cancer Cells. Molecules 2011, 16, 4632-4641.

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