Ascorbate Analogs for Use in Medical Imaging: Synthesis and Radical Scavenging Activity of 5-O-(4′-Iodobenzyl)-L-ascorbic Acid

Abstract

As part of our program to develop potential imaging agents for ascorbate bioactivity in the brain, 5-O-(4′-iodobenzyl)-L-ascorbic acid was prepared through a seven-step sequence which involved C₅-O-alkylation with p-iodobenzyl bromide in the presence of Ag₂O and CaSO₄ as the key step, starting from L-ascorbic acid. The scavenging activity of the p-iodobenzylated analog against 2,2-diphenyl-1-picrylhyrazyl (DPPH) radical was almost the same as that of L-ascorbic acid itself.