Iron overload is a clinical problem which can be prevented by using
iron chelating agents. An alternative method of relieving
iron overload is to reduce
iron absorption from the intestine by administering specific
iron chelating agents, which can bind
iron to form nonabsorbable complexes. Based on this strategy, a series of polymeric
ligands containing the chelating moiety 3-hydroxypyridin-4-ones (
HPOs) were synthesized. The synthetic route involves the benzylation of
hydroxyl group of (2-methyl-3-hydroxypyran-4-one (
maltol) and conversion of benzylated
maltol to 3-benzyloxypyridin-4-one derivatives by using three suitable primary
amines (2,6-diaminohexanoic
acid (
lysine) and 1,6-diaminohexane and 5-aminopentanol). The resulted compounds incorporated into
polymer by copolymerization with
acryloyl chloride using 2, 2'-
azobisisobutyronitrile (
AIBN) as the initiator. Finally, the benzyl groups of
polymers were removed by catalytic hydrogenation (Pd/C). In this work, three final
polymers of HPO derivatives namely poly-2-propylamido-6-(3- hydroxy -1,4-dihydro-2-methy-4-oxopyrid-1-yl)
hexanoic acid, 6-(3-hydroxy-1, 4-dihydro-2-methyl-4-oxopyrid-1-yl) hexyl-1-polypropylamide and 5-(3-hydroxy-1-,4-dihydro-2-methyl-4-oxopyrid-1-yl)-1-polyacrylate
pentane were synthesized. Identification and structural elucidation of compounds were achieved by
proton nuclear magnetic resonance ((1)H NMR),
carbon nuclear magnetic resonance ((13)C NMR) and infrared (IR) spectroscopy.