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New Catechol Derivatives of Safrole and Their Antiproliferative Activity towards Breast Cancer Cells
Departamento de Química, Universidad Técnica Federico Santa María, Av. España N° 1680, Valparaíso, Chile
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
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; in revised form: 31 May 2011 / Accepted: 2 June 2011 / Published: 3 June 2011
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
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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.
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(6):4632-4641.
Madrid Villegas, Alejandro; Espinoza Catalán, Luis; Montenegro Venegas, Iván; Villena García, Joan; Carrasco Altamirano, Héctor. 2011. "New Catechol Derivatives of Safrole and Their Antiproliferative Activity towards Breast Cancer Cells." Molecules 16, no. 6: 4632-4641.