Synthesis of Novel Biaryl Derivatives of Sesamol (5-Benzodioxolol) and Evaluation of their Antioxidant Activity Against DPPH Radical
Sergio A. Rodríguez A B , Mónica A. Nazareno B C and María T. Baumgartner A C
+ Author Affiliations
- Author Affiliations
A Instituto de Investigaciones en Fisicoquímica de Córdoba – CONICET, Departamento Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, Córdoba 5000, Argentina.
B Centro de Investigación y Transferencia de Santiago del Estero – CONICET, Instituto de Ciencias Químicas, Facultad de Agronomía y Agroindustrias, Universidad Nacional de Santiago del Estero, Avenida Belgrano (S) 1912, 4200, Santiago del Estero, Argentina.
C Corresponding authors. Email: manazar2004@yahoo.com; tere@fcq.unc.edu.ar
Australian Journal of Chemistry 66(11) 1334-1341 https://doi.org/10.1071/CH13108
Submitted: 6 March 2013 Accepted: 22 June 2013 Published: 7 August 2013
Abstract
A simple and direct arylation of sesamol with aryl halides by a photoinduced reaction is reported. Five 6-arylsesamol derivatives were synthesized in order to evaluate possible changes in their antioxidant properties as a function of the C6 aryl substituent nature. Extension of the procedure to the reaction with o-dihalobenzenes leads to the synthesis of ring-closure products bearing a tetracyclic aromatic condensed ring system, although in lower overall yields (~45 %). The antioxidant activity of the synthetic derivatives towards 1,1-diphenyl-2-picrylhydrazyl radical was determined taking sesamol as the reference compound. In addition, the relationship between the antiradical activities of these molecules against this radical and the bond dissociation energies of their phenolic O–H group was calculated using computational chemistry methods.
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