Ascorbate analogs for use in medical imaging: synthesis and radical scavenging activity of 5-O-(4'-iodobenzyl)-L-ascorbic acid.
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.
Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan.
Hiroharu
H
Kato
Tomohiro
T
Kino
Fumihiko
F
Yamamoto
Tetsuo
T
Kaneshiro
Takahiro
T
Mukai
Minoru
M
Maeda
D000478:Alkylation; D001205:Ascorbic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D001713:Biphenyl Compounds; D003952:Diagnostic Imaging; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000494:pharmacology*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010851:Picrates / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared
C525972:5-O-(4'-iodobenzyl)-L-ascorbic acid; D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D007202:Indicators and Reagents; D010851:Picrates; C004931:1,1-diphenyl-2-picrylhydrazyl; D001205:Ascorbic Acid