Literature DB >> 21392988

Identification of potent, noncovalent fatty acid amide hydrolase (FAAH) inhibitors.

Darin J Gustin1, Zhihua Ma, Xiaoshan Min, Yihong Li, Christine Hedberg, Cris Guimaraes, Amy C Porter, Michelle Lindstrom, Dianna Lester-Zeiner, Guifen Xu, Timothy J Carlson, Shouhua Xiao, Cesar Meleza, Richard Connors, Zhulun Wang, Frank Kayser.   

Abstract

Starting from a series of ureas that were determined to be mechanism-based inhibitors of FAAH, several spirocyclic ureas and lactams were designed and synthesized. These efforts identified a series of novel, noncovalent FAAH inhibitors with in vitro potency comparable to known covalent FAAH inhibitors. The mechanism of action for these compounds was determined through a combination of SAR and co-crystallography with rat FAAH.
Copyright © 2011 Elsevier Ltd. All rights reserved.

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Year:  2011        PMID: 21392988     DOI: 10.1016/j.bmcl.2011.02.052

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


  11 in total

1.  Transition-metal-free C-H amidation and chlorination: synthesis of N/N'-mono-substituted imidazopyridin-2-ones from N-pyridyl-N-hydroxylamine intermediates.

Authors:  Katarzyna N Lee; Dominique N Spiegowski; Johnny W Lee; Sanghyun Lim; Fuhua Zhao; Ming-Yu Ngai
Journal:  Chem Commun (Camb)       Date:  2018-06-19       Impact factor: 6.222

2.  Biphenyl-3-yl alkylcarbamates as fatty acid amide hydrolase (FAAH) inhibitors: steric effects of N-alkyl chain on rat plasma and liver stability.

Authors:  Federica Vacondio; Claudia Silva; Alessio Lodola; Caterina Carmi; Silvia Rivara; Andrea Duranti; Andrea Tontini; Silvano Sanchini; Jason R Clapper; Daniele Piomelli; Giorgio Tarzia; Marco Mor
Journal:  Eur J Med Chem       Date:  2011-07-21       Impact factor: 6.514

Review 3.  The discovery and development of inhibitors of fatty acid amide hydrolase (FAAH).

Authors:  Katerina Otrubova; Cyrine Ezzili; Dale L Boger
Journal:  Bioorg Med Chem Lett       Date:  2011-06-28       Impact factor: 2.823

4.  Preclinical Characterization of the FAAH Inhibitor JNJ-42165279.

Authors:  John M Keith; William M Jones; Mark Tichenor; Jing Liu; Mark Seierstad; James A Palmer; Michael Webb; Mark Karbarz; Brian P Scott; Sandy J Wilson; Lin Luo; Michelle L Wennerholm; Leon Chang; Michele Rizzolio; Raymond Rynberg; Sandra R Chaplan; J Guy Breitenbucher
Journal:  ACS Med Chem Lett       Date:  2015-11-02       Impact factor: 4.345

5.  Discovery and molecular basis of potent noncovalent inhibitors of fatty acid amide hydrolase (FAAH).

Authors:  Xiaoshan Min; Stephen T Thibault; Amy C Porter; Darin J Gustin; Timothy J Carlson; Haoda Xu; Michelle Lindstrom; Guifen Xu; Craig Uyeda; Zhihua Ma; Yihong Li; Frank Kayser; Nigel P C Walker; Zhulun Wang
Journal:  Proc Natl Acad Sci U S A       Date:  2011-04-18       Impact factor: 11.205

6.  Optimization of 1,2,5-thiadiazole carbamates as potent and selective ABHD6 inhibitors.

Authors:  Jayendra Z Patel; Tapio J Nevalainen; Juha R Savinainen; Yahaya Adams; Tuomo Laitinen; Robert S Runyon; Miia Vaara; Stephen Ahenkorah; Agnieszka A Kaczor; Dina Navia-Paldanius; Mikko Gynther; Niina Aaltonen; Amit A Joharapurkar; Mukul R Jain; Abigail S Haka; Frederick R Maxfield; Jarmo T Laitinen; Teija Parkkari
Journal:  ChemMedChem       Date:  2014-12-11       Impact factor: 3.466

7.  Discovery of MK-4409, a Novel Oxazole FAAH Inhibitor for the Treatment of Inflammatory and Neuropathic Pain.

Authors:  Harry R Chobanian; Yan Guo; Ping Liu; Marc D Chioda; Selena Fung; Thomas J Lanza; Linda Chang; Raman K Bakshi; James P Dellureficio; Qingmei Hong; Mark McLaughlin; Kevin M Belyk; Shane W Krska; Amanda K Makarewicz; Elliot J Martel; Joseph F Leone; Lisa Frey; Bindhu Karanam; Maria Madeira; Raul Alvaro; Joyce Shuman; Gino Salituro; Jenna L Terebetski; Nina Jochnowitz; Shruti Mistry; Erin McGowan; Richard Hajdu; Mark Rosenbach; Catherine Abbadie; Jessica P Alexander; Lin-Lin Shiao; Kathleen M Sullivan; Ravi P Nargund; Matthew J Wyvratt; Linus S Lin; Robert J DeVita
Journal:  ACS Med Chem Lett       Date:  2014-04-10       Impact factor: 4.345

8.  Design, synthesis, and characterization of α-ketoheterocycles that additionally target the cytosolic port Cys269 of fatty acid amide hydrolase.

Authors:  Katerina Otrubova; Benjamin F Cravatt; Dale L Boger
Journal:  J Med Chem       Date:  2014-01-23       Impact factor: 7.446

9.  Interaction of the N-(3-Methylpyridin-2-yl)amide Derivatives of Flurbiprofen and Ibuprofen with FAAH: Enantiomeric Selectivity and Binding Mode.

Authors:  Jessica Karlsson; Carmine M Morgillo; Alessandro Deplano; Giovanni Smaldone; Emilia Pedone; F Javier Luque; Mona Svensson; Ettore Novellino; Cenzo Congiu; Valentina Onnis; Bruno Catalanotti; Christopher J Fowler
Journal:  PLoS One       Date:  2015-11-13       Impact factor: 3.240

10.  Benzylamides and piperazinoarylamides of ibuprofen as fatty acid amide hydrolase inhibitors.

Authors:  Alessandro Deplano; Mariateresa Cipriano; Federica Moraca; Ettore Novellino; Bruno Catalanotti; Christopher J Fowler; Valentina Onnis
Journal:  J Enzyme Inhib Med Chem       Date:  2019-12       Impact factor: 5.051

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