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Benzothiophene piperazine and piperidine urea inhibitors of fatty acid amide hydrolase (FAAH)

Academic Article
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Overview

authors

  • Johnson, Doug
  • Ahn, K.
  • Kesten, S.
  • Lazerwith, S. E.
  • Song, Y.
  • Morris, M.
  • Fay, L.
  • Gregory, T.
  • Stiff, C.
  • Dunbar, J. B.
  • Liimatta, M.
  • Beidler, D.
  • Smith, S.
  • Nomanbhoy, T. K.
  • Cravatt, Benjamin

publication date

  • May 2009

journal

  • Bioorganic & Medicinal Chemistry Letters  Journal

abstract

  • The synthesis and structure-activity relationships (SAR) of a series of benzothiophene piperazine and piperidine urea FAAH inhibitors is described. These compounds inhibit FAAH by covalently modifying the enzyme's active site serine nucleophile. Activity-based protein profiling (ABPP) revealed that these urea inhibitors were completely selective for FAAH relative to other mammalian serine hydrolases. Several compounds showed in vivo activity in a rat complete Freund's adjuvant (CFA) model of inflammatory pain.

subject areas

  • Amidohydrolases
  • Animals
  • Computer Simulation
  • Enzyme Inhibitors
  • Humans
  • Models, Chemical
  • Piperazines
  • Piperidines
  • Rats
  • Structure-Activity Relationship
  • Thiophenes
  • Urea
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Research

keywords

  • Activity-based protein profiling
  • Covalent inhibitor
  • FAAH inhibitor
  • Fatty acid amide hydrolase
  • Urea
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Identity

PubMed Central ID

  • PMC3150822

International Standard Serial Number (ISSN)

  • 0960-894X

Digital Object Identifier (DOI)

  • 10.1016/j.bmcl.2009.03.080

PubMed ID

  • 19386497
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Additional Document Info

start page

  • 2865

end page

  • 2869

volume

  • 19

issue

  • 10

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