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.
Serwa
Remigiusz
R
Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, USA.
Nam
Tae-gyu
TG
Valgimigli
Luca
L
Culbertson
Sean
S
Rector
Christopher L
CL
Jeong
Byeong-Seon
BS
Pratt
Derek A
DA
Porter
Ned A
NA
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