Literature DB >> 19386497

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

Douglas S Johnson1, Kay Ahn, Suzanne Kesten, Scott E Lazerwith, Yuntao Song, Mark Morris, Lorraine Fay, Tracy Gregory, Cory Stiff, James B Dunbar, Marya Liimatta, David Beidler, Sarah Smith, Tyzoon K Nomanbhoy, Benjamin F Cravatt.   

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.

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Year:  2009        PMID： 19386497      PMCID： PMC3150822          DOI： 10.1016/j.bmcl.2009.03.080

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  30 in total

1.  Activity-based protein profiling: the serine hydrolases.

Authors:  Y Liu; M P Patricelli; B F Cravatt
Journal:  Proc Natl Acad Sci U S A       Date:  1999-12-21       Impact factor: 11.205

2.  Modulation of anxiety through blockade of anandamide hydrolysis.

Authors:  Satish Kathuria; Silvana Gaetani; Darren Fegley; Fernando Valiño; Andrea Duranti; Andrea Tontini; Marco Mor; Giorgio Tarzia; Giovanna La Rana; Antonio Calignano; Arcangela Giustino; Maria Tattoli; Maura Palmery; Vincenzo Cuomo; Daniele Piomelli
Journal:  Nat Med       Date:  2002-12-02       Impact factor: 53.440

Review 3.  The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications.

Authors:  Didier M Lambert; Christopher J Fowler
Journal:  J Med Chem       Date:  2005-08-11       Impact factor: 7.446

Review 4.  Discovery and development of fatty acid amide hydrolase (FAAH) inhibitors.

Authors:  Mark Seierstad; J Guy Breitenbucher
Journal:  J Med Chem       Date:  2008-12-11       Impact factor: 7.446

Review 5.  Activity-based protein profiling: from enzyme chemistry to proteomic chemistry.

Authors:  Benjamin F Cravatt; Aaron T Wright; John W Kozarich
Journal:  Annu Rev Biochem       Date:  2008       Impact factor: 23.643

6.  Synthesis and structure-activity relationships of FAAH inhibitors: cyclohexylcarbamic acid biphenyl esters with chemical modulation at the proximal phenyl ring.

Authors:  Giorgio Tarzia; Andrea Duranti; Giuseppe Gatti; Giovanni Piersanti; Andrea Tontini; Silvia Rivara; Alessio Lodola; Pier Vincenzo Plazzi; Marco Mor; Satish Kathuria; Daniele Piomelli
Journal:  ChemMedChem       Date:  2006-01       Impact factor: 3.466

7.  Supersensitivity to anandamide and enhanced endogenous cannabinoid signaling in mice lacking fatty acid amide hydrolase.

Authors:  B F Cravatt; K Demarest; M P Patricelli; M H Bracey; D K Giang; B R Martin; A H Lichtman
Journal:  Proc Natl Acad Sci U S A       Date:  2001-07-24       Impact factor: 11.205

8.  Cyclohexylcarbamic acid 3'- or 4'-substituted biphenyl-3-yl esters as fatty acid amide hydrolase inhibitors: synthesis, quantitative structure-activity relationships, and molecular modeling studies.

Authors:  Marco Mor; Silvia Rivara; Alessio Lodola; Pier Vincenzo Plazzi; Giorgio Tarzia; Andrea Duranti; Andrea Tontini; Giovanni Piersanti; Satish Kathuria; Daniele Piomelli
Journal:  J Med Chem       Date:  2004-10-07       Impact factor: 7.446

Review 9.  Fatty acid amide hydrolase: an emerging therapeutic target in the endocannabinoid system.

Authors:  Benjamin F Cravatt; Aron H Lichtman
Journal:  Curr Opin Chem Biol       Date:  2003-08       Impact factor: 8.822

10.  Optimization of the central heterocycle of alpha-ketoheterocycle inhibitors of fatty acid amide hydrolase.

Authors:  Joie Garfunkle; Cyrine Ezzili; Thomas J Rayl; Dustin G Hochstatter; Inkyu Hwang; Dale L Boger
Journal:  J Med Chem       Date:  2008-07-16       Impact factor: 7.446
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  25 in total

1.  Covalent inhibitors of fatty acid amide hydrolase: a rationale for the activity of piperidine and piperazine aryl ureas.

Authors:  Giulia Palermo; Davide Branduardi; Matteo Masetti; Alessio Lodola; Marco Mor; Daniele Piomelli; Andrea Cavalli; Marco De Vivo
Journal:  J Med Chem       Date:  2011-09-08       Impact factor: 7.446

2.  Strategies for discovering and derisking covalent, irreversible enzyme inhibitors.

Authors:  Douglas S Johnson; Eranthie Weerapana; Benjamin F Cravatt
Journal:  Future Med Chem       Date:  2010-06       Impact factor: 3.808

3.  O-(triazolyl)methyl carbamates as a novel and potent class of fatty acid amide hydrolase (FAAH) inhibitors.

Authors:  Giampiero Colombano; Clara Albani; Giuliana Ottonello; Alison Ribeiro; Rita Scarpelli; Glauco Tarozzo; Jennifer Daglian; Kwang-Mook Jung; Daniele Piomelli; Tiziano Bandiera
Journal:  ChemMedChem       Date:  2014-10-22       Impact factor: 3.466

4.  Identification and optimization of soluble epoxide hydrolase inhibitors with dual potency towards fatty acid amide hydrolase.

Authors:  Sean D Kodani; Saavan Bhakta; Sung Hee Hwang; Svetlana Pakhomova; Marcia E Newcomer; Christophe Morisseau; Bruce D Hammock
Journal:  Bioorg Med Chem Lett       Date:  2018-01-04       Impact factor: 2.823

5.  Discovery of PF-04457845: A Highly Potent, Orally Bioavailable, and Selective Urea FAAH Inhibitor.

Authors:  Douglas S Johnson; Cory Stiff; Scott E Lazerwith; Suzanne R Kesten; Lorraine K Fay; Mark Morris; David Beidler; Marya B Liimatta; Sarah E Smith; David T Dudley; Nalini Sadagopan; Shobha N Bhattachar; Stephen J Kesten; Tyzoon K Nomanbhoy; Benjamin F Cravatt; Kay Ahn
Journal:  ACS Med Chem Lett       Date:  2011-02-10       Impact factor: 4.345

6.  Rational design of fatty acid amide hydrolase inhibitors that act by covalently bonding to two active site residues.

Authors:  Katerina Otrubova; Monica Brown; Michael S McCormick; Gye W Han; Scott T O'Neal; Benjamin F Cravatt; Raymond C Stevens; Aron H Lichtman; Dale L Boger
Journal:  J Am Chem Soc       Date:  2013-04-12       Impact factor: 15.419

7.  Evaluation of phenoxybenzamine in the CFA model of pain following gene expression studies and connectivity mapping.

Authors:  Meiping Chang; Sarah Smith; Andrew Thorpe; Michael J Barratt; Farzana Karim
Journal:  Mol Pain       Date:  2010-09-16       Impact factor: 3.395

8.  Piperidinyl thiazole isoxazolines: A new series of highly potent, slowly reversible FAAH inhibitors with analgesic properties.

Authors:  Stephen O Pember; Galo L Mejia; Theodore J Price; Robert J Pasteris
Journal:  Bioorg Med Chem Lett       Date:  2016-02-22       Impact factor: 2.823

9.  X-ray crystallographic analysis of alpha-ketoheterocycle inhibitors bound to a humanized variant of fatty acid amide hydrolase.

Authors:  Mauro Mileni; Joie Garfunkle; Cyrine Ezzili; F Scott Kimball; Benjamin F Cravatt; Raymond C Stevens; Dale L Boger
Journal:  J Med Chem       Date:  2010-01-14       Impact factor: 7.446

10.  Discovery libraries targeting the major enzyme classes: the serine hydrolases.

Authors:  Katerina Otrubova; Venkat Srinivasan; Dale L Boger
Journal:  Bioorg Med Chem Lett       Date:  2014-06-27       Impact factor: 2.823
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