Síntesis de nuevos derivados del eugenol con actividad dual para el tratamiento de la enfermedad de alzheimer

Abstract

In this research chemical modification of eugenol, coming from clove essential oil (Eugenia caryophyllus), was studied in order to generate new compounds with potential antioxidant activity and acetylcholinesterase inhibitory activity. Because of their dual activities, these compounds are presented here as promising for pharmacological studies related to Alzheimer’s disease treatment. The essential oil Eugenia caryophyllus was extracted from clove, acquired in the local market, by means of a conventional distillation method for increased extraction. The characterization of this oil revealed that it contains 11 compounds, where eugenol occurred as the major component, this is 71%. Eugenol was isolated from the essential oil for its subsequent chemical modification. For the synthesis of the 9 new compounds 3 starting compounds were used: Eugenol, isoeugenol and hydrogenated eugenol which were subjected to O-alkylation reactions, by using bromides of ethyl, butyl and octyl as alkylating compounds. Each one was characterized physically (m.p., Rf) and spectrometrically (IR, CG-MS, RMN 1H and 13C). For testing their pharmacological activities, two assays of antioxidant and acetylcholinesterase inhibitory activity were made. For antioxidant activity, it was calculated the TEAC value for each synthesized compound using Trolox® as a reference compound, and Vitamin E (α-tocopherol), butylhydroxyanisole and butylhydroxytoluene as control compounds. The values of TEAC are in the range of 6.93x10-8-3.26x10-7. In the inhibitory activity of the enzyme, values of IC50 to 21.29-57.19 μg/mL were found. The obtained results of this investigation were released to the scientific community by presenting a paper at the Latinamerican Congress of Chemistry CLAQ 2014.