Preparation and Investigation of Vitamin B-6-Derived Aminopyridinol Antioxidants

Abstract

3-Pyridinols bearing amine substitution para to the hydroxylic moiety have previously been shown to inhibit lipid peroxidation more effectively than typical phenolic antioxidants, for example, alpha-tocopherol. We report here high-yielding, large-scale syntheses of mono- and bicyclic amino-pyridinols from pyridoxine hydrochloride (i.e., vitamin B6). This approach provides straightforward, scaleable access to novel, potent, molecular scaffolds whose antioxidant properties have been investigated in homogeneous solutions and in liposomal vesicles. These molecular aggregates mimic cell membranes that are the targets of oxidative damage in vivo.