Literature DB >> 11735566

2-Aryl-2,2-difluoroacetamide FKBP12 ligands: synthesis and X-ray structural studies.

G M Dubowchik1, V M Vrudhula, B Dasgupta, J Ditta, T Chen, S Sheriff, K Sipman, M Witmer, J Tredup, D M Vyas, T A Verdoorn, S Bollini, A 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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Year:  2001        PMID： 11735566     DOI： 10.1021/ol0166909

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  6 in total

1.  Regio- and Enantioselective Bromocyclization of Difluoroalkenes as a Strategy to Access Tetrasubstituted Difluoromethylene-Containing Stereocenters.

Authors:  Edward Miller; Suhong Kim; Katarina Gibson; Jeffrey S Derrick; F Dean Toste
Journal:  J Am Chem Soc       Date:  2020-04-30       Impact factor: 15.419

2.  Synthesis of Aryldifluoroamides by Copper-Catalyzed Cross-Coupling.

Authors:  Sophie I Arlow; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-01       Impact factor: 15.336

3.  Bioluminescent sensor proteins for point-of-care therapeutic drug monitoring.

Authors:  Rudolf Griss; Alberto Schena; Luc Reymond; Luc Patiny; Dominique Werner; Christine E Tinberg; David Baker; Kai Johnsson
Journal:  Nat Chem Biol       Date:  2014-06-08       Impact factor: 15.040

4.  The utility of geometrical and chemical restraint information extracted from predicted ligand-binding sites in protein structure refinement.

Authors:  Michal Brylinski; Seung Yup Lee; Hongyi Zhou; Jeffrey Skolnick
Journal:  J Struct Biol       Date:  2010-09-17       Impact factor: 2.867

5.  Pd-catalyzed α-arylation of trimethylsilyl enolates of α,α-difluoroacetamides.

Authors:  Shaozhong Ge; Sophie I Arlow; Michael G Mormino; John F Hartwig
Journal:  J Am Chem Soc       Date:  2014-10-03       Impact factor: 15.419

6.  Synthesis of Fluorinated Amide Derivatives via a Radical N-Perfluoroalkylation-Defluorination Pathway.

Authors:  Zhiyao Zheng; Angela van der Werf; Marie Deliaval; Nicklas Selander
Journal:  Org Lett       Date:  2020-03-25       Impact factor: 6.005
  6 in total

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