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Exploration of a fundamental substituent effect of α-ketoheterocycle enzyme inhibitors: Potent and selective inhibitors of fatty acid amide hydrolase

Academic Article
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Overview

related to degree

  • Garfunkle, Joie, Ph.D. in Chemistry, Scripps Research 2004 - 2009
  • DeMartino, Jessica, Ph.D. in Chemistry, Scripps Research 2003 - 2008

authors

  • DeMartino, Jessica
  • Garfunkle, Joie
  • Hochstatter, D. G.
  • Cravatt, Benjamin
  • Boger, Dale

publication date

  • November 2008

journal

  • Bioorganic & Medicinal Chemistry Letters  Journal

abstract

  • A series of C4 substituted alpha-ketooxazoles were examined as inhibitors of the serine hydrolase fatty acid amide hydrolase in efforts that further define and generalize a fundamental substituent effect on enzyme inhibitory potency. Thus, a plot of the Hammett sigma(m) versus -logK(i) provided a linear correlation (R(2)=0.90) with a slope of 3.37 (rho=3.37), that is of a magnitude that indicates that of the electron-withdrawing character of the substituent dominates its effects (a one unit change in sigma(m) provides a >1000-fold change in K(i)).

subject areas

  • Amidohydrolases
  • Amino Acid Sequence
  • Drug Design
  • Molecular Structure
  • Oxazoles
  • Structure-Activity Relationship
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Research

keywords

  • Fatty acid amide hydrolase
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Identity

PubMed Central ID

  • PMC2582052

International Standard Serial Number (ISSN)

  • 0960-894X

Digital Object Identifier (DOI)

  • 10.1016/j.bmcl.2008.06.084

PubMed ID

  • 18639454
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Additional Document Info

start page

  • 5842

end page

  • 5846

volume

  • 18

issue

  • 22

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