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The Synthesis and Characterization of Masked Iron Chelators
- Abstract:
The synthesis of arylboronic esters was investigated to find masked iron chelators suitable for potential neurodegenerative disease treatment. A known iron chelator is ‘masked’ by a boronic ester functionality, allowing selective chelation of iron under oxidative conditions. Arylboronates were synthesized in low yields by a palladium catalyzed reaction of aryl-halides or -triflates with bis(pinacolatodiboron) or pinacolborane (HBpin). Target molecules BHPA (3-boronic acid-4-pyridinone) and BHQ (8-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-quinoline) require further study for increased yields. BHQA (8-quinolineboronic acid) has been used to demonstrate H2O2 promoted oxidation of the B-C bond, and subsequent iron binding by the resulting HQ (8-hydroxyquinoline).
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