Preparation and investigation of vitamin B6-derived aminopyridinol antioxidants.
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, α-tocopherol. We report here high-yielding, large-scale syntheses of mono- and bicyclic aminopyridinols from pyridoxine hydrochloride (i.e., vitamin B(6)). 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.
Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, USA.
Remigiusz
R
Serwa
Tae-gyu
TG
Nam
Luca
L
Valgimigli
Sean
S
Culbertson
Christopher L
CL
Rector
Byeong-Seon
BS
Jeong
Derek A
DA
Pratt
Ned A
NA
Porter
D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry*; D000631:Aminopyridines / Q000138:chemical synthesis* / Q000737:chemistry*; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry*; D016166:Free Radical Scavengers / Q000737:chemistry*; D006801:Humans; D015227:Lipid Peroxidation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D025101:Vitamin B 6 / Q000737:chemistry*; D024502:alpha-Tocopherol / Q000737:chemistry*
D000605:Amino Alcohols; D000631:Aminopyridines; D000975:Antioxidants; D016166:Free Radical Scavengers; D025101:Vitamin B 6; D024502:alpha-Tocopherol