Literature DB >> 18693015

Thiadiazolopiperazinyl ureas as inhibitors of fatty acid amide hydrolase.

John M Keith1, Richard Apodaca, Wei Xiao, Mark Seierstad, Kanaka Pattabiraman, Jiejun Wu, Michael Webb, Mark J Karbarz, Sean Brown, Sandy Wilson, Brian Scott, Chui-Se Tham, Lin Luo, James Palmer, Michelle Wennerholm, Sandra Chaplan, J Guy Breitenbucher.   

Abstract

A series of thiadiazolopiperazinyl aryl urea fatty acid amide hydrolase (FAAH) inhibitors is described. The molecules were found to inhibit the enzyme by acting as mechanism-based substrates, forming a covalent bond with Ser241. SAR and PK properties are presented.

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Year:  2008        PMID： 18693015     DOI： 10.1016/j.bmcl.2008.07.081

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


  31 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.  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

4.  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

5.  Quantum mechanics/molecular mechanics modeling of fatty acid amide hydrolase reactivation distinguishes substrate from irreversible covalent inhibitors.

Authors:  Alessio Lodola; Luigi Capoferri; Silvia Rivara; Giorgio Tarzia; Daniele Piomelli; Adrian Mulholland; Marco Mor
Journal:  J Med Chem       Date:  2013-03-07       Impact factor: 7.446

6.  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

Review 7.  Marijuana, Spice 'herbal high', and early neural development: implications for rescheduling and legalization.

Authors:  Delphine Psychoyos; K Yaragudri Vinod
Journal:  Drug Test Anal       Date:  2012-08-13       Impact factor: 3.345

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

Authors:  Douglas S Johnson; 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
Journal:  Bioorg Med Chem Lett       Date:  2009-03-24       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 and characterization of a highly selective FAAH inhibitor that reduces inflammatory pain.

Authors:  Kay Ahn; Douglas S Johnson; Mauro Mileni; David Beidler; Jonathan Z Long; Michele K McKinney; Eranthie Weerapana; Nalini Sadagopan; Marya Liimatta; Sarah E Smith; Scott Lazerwith; Cory Stiff; Satwik Kamtekar; Keshab Bhattacharya; Yanhua Zhang; Stephen Swaney; Keri Van Becelaere; Raymond C Stevens; Benjamin F Cravatt
Journal:  Chem Biol       Date:  2009-04-24
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