Next Article in Journal
Statistical Optimization of Medium for Pullulan Production by Aureobasidium pullulans NCPS2016 Using Fructose and Soybean Meal Hydrolysates
Next Article in Special Issue
Ferrocenes as Building Blocks in Molecular Rectifiers and Diodes
Previous Article in Journal
Aromaticity as a Guiding Concept for Spectroscopic Features and Nonlinear Optical Properties of Porphyrinoids
Previous Article in Special Issue
Enantiomerically Enriched 1,2-P,N-Bidentate Ferrocenyl Ligands for 1,3-Dipolar Cycloaddition and Transfer Hydrogenation Reactions
Article Menu
Issue 6 (June) cover image

Export Article

Open AccessArticle
Molecules 2018, 23(6), 1335; https://doi.org/10.3390/molecules23061335

Trapping para-Quinone Methide Intermediates with Ferrocene: Synthesis and Preliminary Biological Evaluation of New Phenol-Ferrocene Conjugates

1
Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo, Julián Clavería 8, 33006 Oviedo, Spain
2
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
3
Departamento de Química Física y Analítica, Universidad de Oviedo, Julián Clavería 8, 33006 Oviedo, Spain
*
Author to whom correspondence should be addressed.
Received: 9 May 2018 / Revised: 29 May 2018 / Accepted: 29 May 2018 / Published: 1 June 2018
(This article belongs to the Special Issue Ferrocene and Ferrocene-Containing Compounds)
Full-Text   |   PDF [2273 KB, uploaded 2 June 2018]   |  

Abstract

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. View Full-Text
Keywords: ferrocene; phenol; para-quinone methides; cytotoxic activity ferrocene; phenol; para-quinone methides; cytotoxic activity
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary material

SciFeed

Share & Cite This Article

MDPI and ACS Style

González-Pelayo, S.; López, E.; Borge, J.; de-los-Santos-Álvarez, N.; López, L.A. Trapping para-Quinone Methide Intermediates with Ferrocene: Synthesis and Preliminary Biological Evaluation of New Phenol-Ferrocene Conjugates. Molecules 2018, 23, 1335.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top