114 Development of Isocyanate Reagents for the Preparation of Carbamate and Urea Linked Hydroxamic Acid and 2,3-Hydroxypyridinone (HOPO) Chelators

Wednesday, November 4, 2009: 9:00 AM
Rio Grande (Camino Real Hotel)
Rasika Fernando , Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, NM
Hollie K. Jacobs , Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, NM
Aravamudan S. Gopalan , Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, NM
Iron chelators play a complex and pivotal role in biological systems. The therapeutic value of iron chelators in the treatment of a variety of diseases has led to much interest in the preparation of synthetic hydroxypyridinone and hydroxamic acid chelators that mimic natural siderophores.  New methods are needed for the tethering of ligand moieties to a variety of structural motifs which in turn will allow the creation of a new generation of hosts to bind iron(III) selectively.  The specific goal of this project is to generate new synthetic methods that would allow the tethering of N-alkyl hydroxamic acids and 3,2-hydroxypyridinones (HOPO) to amines and alcohols through a carbamate or urea linkage.  In this context, two new isocyanate reagents carrying the HOPO and hydroxamic acid moieties have been prepared and their reactivity examined.  This work also has led to the preparation of a novel class of potential iron chelating agents whose binding properties are under evaluation.
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