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Delineation of a fundamental alpha-ketoheterocycle substituent effect for use in the design of enzyme inhibitors

Academic Article
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Overview

authors

  • Romero, F. A.
  • Hwang, I.
  • Boger, Dale

publication date

  • November 2006

journal

  • Journal of the American Chemical Society  Journal

abstract

  • The synthesis and examination of a systematic series of 5-substituted 2-keto oxazoles as inhibitors of fatty acid amide hydrolase (FAAH) defined a fundamental substituent effect that led to the discovery of inhibitors with Ki's as low as 400 pM. The intrinsic basis of the relationship (-log Ki vs sigmap), which relates Ki with the Hammett sigmap constant of the substituent, the magnitude of the effect (rho = 3.01), and its predictive value (R2 = 0.91) suggest a widespread applicability in studies beyond FAAH.

subject areas

  • Drug Design
  • Enzyme Inhibitors
  • Heterocyclic Compounds
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Identity

PubMed Central ID

  • PMC2501112

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja064522b

PubMed ID

  • 17061864
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Additional Document Info

start page

  • 14004

end page

  • 14005

volume

  • 128

issue

  • 43

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