Literature DB >> 18983140

Discovery of boronic acids as novel and potent inhibitors of fatty acid amide hydrolase.

Anna Minkkilä1, Susanna M Saario, Heikki Käsnänen, Jukka Leppänen, Antti Poso, Tapio Nevalainen.   

Abstract

A series of commercial phenyl-, heteroaryl-, alkyl-, and alkenylboronic acids were evaluated for their FAAH and MGL inhibitory activities. The compounds were generally selective for FAAH, with IC50 in the nanomolar or low-micromolar range. Eight of these compounds inhibited MGL with IC50 in the micromolar range. The most potent compound, phenylboronic acid with para-nonyl substituent (13), inhibited FAAH and MGL with IC50 of 0.0091 and 7.9 microM, respectively.

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Year:  2008        PMID: 18983140     DOI: 10.1021/jm801051t

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  13 in total

1.  A second generation of carbamate-based fatty acid amide hydrolase inhibitors with improved activity in vivo.

Authors:  Jason R Clapper; Federica Vacondio; Alvin R King; Andrea Duranti; Andrea Tontini; Claudia Silva; Silvano Sanchini; Giorgio Tarzia; Marco Mor; Daniele Piomelli
Journal:  ChemMedChem       Date:  2009-09       Impact factor: 3.466

2.  A methodology for radiolabeling of the endocannabinoid 2-arachidonoylglycerol (2-AG).

Authors:  Richard I Duclos; Meghan Johnston; Subramanian K Vadivel; Alexandros Makriyannis; Sherrye T Glaser; S John Gatley
Journal:  J Org Chem       Date:  2011-03-03       Impact factor: 4.354

3.  Boronic acids as tools to study (plant) developmental processes?

Authors:  Michaela Matthes; Ramón A Torres-Ruiz
Journal:  Plant Signal Behav       Date:  2017-04-27

Review 4.  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

5.  Fatty acid amide hydrolase as a potential therapeutic target for the treatment of pain and CNS disorders.

Authors:  Kay Ahn; Douglas S Johnson; Benjamin F Cravatt
Journal:  Expert Opin Drug Discov       Date:  2009-07       Impact factor: 6.098

6.  Fluoride-mediated capture of a noncovalent bound state of a reversible covalent enzyme inhibitor: X-ray crystallographic analysis of an exceptionally potent α-ketoheterocycle inhibitor of fatty acid amide hydrolase.

Authors:  Mauro Mileni; Joie Garfunkle; Cyrine Ezzili; Benjamin F Cravatt; Raymond C Stevens; Dale L Boger
Journal:  J Am Chem Soc       Date:  2011-02-28       Impact factor: 15.419

7.  Carborane clusters in computational drug design: a comparative docking evaluation using AutoDock, FlexX, Glide, and Surflex.

Authors:  Rohit Tiwari; Kiran Mahasenan; Ryan Pavlovicz; Chenglong Li; Werner Tjarks
Journal:  J Chem Inf Model       Date:  2009-06       Impact factor: 4.956

8.  Synthesis and evaluation of 4-(substituted styryl/alkenyl)-3,5-bis(4-hydroxyphenyl)-isoxazoles as ligands for the estrogen receptor.

Authors:  Terra Haddad; Rachel Gershman; Robert Dilis; David Labaree; Richard B Hochberg; Robert N Hanson
Journal:  Bioorg Med Chem Lett       Date:  2012-07-15       Impact factor: 2.823

9.  (4-Carbamoylphen-yl)boronic acid.

Authors:  Margarita D Apostolova; Rositsa P Nikolova; Boris L Shivachev
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-05-08

10.  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

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