Trapping para-Quinone Methide Intermediates with Ferrocene: Synthesis and Preliminary Biological Evaluation of New Phenol-Ferrocene Conjugates
Silvia González-Pelayo,
Enol López,
Javier Borge,
Noemí de-los-Santos-Álvarez,
Luis A. López
Affiliations
Silvia González-Pelayo
Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo, Julián Clavería 8, 33006 Oviedo, Spain
Enol López
Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo, Julián Clavería 8, 33006 Oviedo, Spain
Javier Borge
Laboratorio de Compuestos Organometálicos y Catálisis (Unidad Asociada al CSIC), Centro de Innovación en Química Avanzada (ORFEO-CINQA) and Departamento de Química Física y Analítica, Universidad de Oviedo, Julián Clavería 8, 33006 Oviedo, Spain
Noemí de-los-Santos-Álvarez
Departamento de Química Física y Analítica, Universidad de Oviedo, Julián Clavería 8, 33006 Oviedo, Spain
Luis A. López
Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo, Julián Clavería 8, 33006 Oviedo, Spain
The reaction of para-hydroxybenzyl alcohols with ferrocene in the presence of a catalytic amount of InCl3 provided ferrocenyl phenol derivatives, an interesting class of organometallic compounds with potential applications in medicinal chemistry. This transformation exhibited a reasonable substrate scope delivering the desired products in synthetically useful yields. Evidence of involvement of a para-quinone methide intermediate in this coupling process was also provided. Preliminary biological evaluation demonstrated that some of the ferrocene derivatives available by this methodology exhibit significant cytotoxicity against several cancer cell lines with IC50 values within the range of 1.07–4.89 μM.
