2-Aryl-2,2-difluoroacetamide FKBP12 Ligands: Synthesis and X-ray Structural Studies
Organic Letters2001Vol. 3(25), pp. 3987–3990
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Gene M. Dubowchik, Vivekananda M. Vrudhula, Bireshwar Dasgupta, Jonathan L. Ditta, Ti Chen, S. Sheriff, Karin Sipman, Mark R. Witmer, Jeffrey Tredup, Dolatrai M. Vyas, Todd A. Verdoorn, Sagarika Bollini, Alexander Vinitsky
Abstract
[structure: see text] 2-Aryl-2,2-difluoroacetamido-proline and pipecolate esters are high affinity FKBP12 ligands whose rotamase inhibitory activity is comparable to that seen for the corresponding ketoamides. X-ray structural studies suggest that the fluorine atoms participate in discrete interactions with the Phe36 phenyl ring and the Tyr26 hydroxyl group, with the latter resembling a moderate-to-weak hydrogen bond.
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