Literature DB >> 11412972

alpha-Keto heterocycle inhibitors of fatty acid amide hydrolase: carbonyl group modification and alpha-substitution.

D L Boger1, H Miyauchi, M P Hedrick.   

Abstract

Two sets of novel analogues of the recently disclosed alpha-keto heterocycle inhibitors of fatty acid amide hydrolase (FAAH), the enzyme responsible for regulation of endogenous oleamide and anandamide, were synthesized and evaluated in order to clarify a role of the electrophilic carbonyl group and structural features important for their activity. Both the electrophilic carbonyl and the degree of alpha-substitution markedly affect inhibitor potency.

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Year:  2001        PMID： 11412972     DOI： 10.1016/s0960-894x(01)00211-6

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


  24 in total

1.  Toward an anandamide transporter.

Authors:  Raphael Mechoulam; Dale G Deutsch
Journal:  Proc Natl Acad Sci U S A       Date:  2005-11-28       Impact factor: 11.205

2.  Exploration of a fundamental substituent effect of alpha-ketoheterocycle enzyme inhibitors: Potent and selective inhibitors of fatty acid amide hydrolase.

Authors:  Jessica K DeMartino; Joie Garfunkle; Dustin G Hochstatter; Benjamin F Cravatt; Dale L Boger
Journal:  Bioorg Med Chem Lett       Date:  2008-06-28       Impact factor: 2.823

3.  Potent and selective alpha-ketoheterocycle-based inhibitors of the anandamide and oleamide catabolizing enzyme, fatty acid amide hydrolase.

Authors:  F Anthony Romero; Wu Du; Inkyu Hwang; Thomas J Rayl; F Scott Kimball; Donmienne Leung; Heather S Hoover; Richard L Apodaca; J Guy Breitenbucher; Benjamin F Cravatt; Dale L Boger
Journal:  J Med Chem       Date:  2007-02-06       Impact factor: 7.446

4.  Design of Benzoxathiazin-3-one 1,1-Dioxides as a New Class of Irreversible Serine Hydrolase Inhibitors: Discovery of a Uniquely Selective PNPLA4 Inhibitor.

Authors:  Anne F Kornahrens; Armand B Cognetta; Daniel M Brody; Megan L Matthews; Benjamin F Cravatt; Dale L Boger
Journal:  J Am Chem Soc       Date:  2017-05-12       Impact factor: 15.419

5.  Delineation of a fundamental alpha-ketoheterocycle substituent effect for use in the design of enzyme inhibitors.

Authors:  F Anthony Romero; Inkyu Hwang; Dale L Boger
Journal:  J Am Chem Soc       Date:  2006-11-01       Impact factor: 15.419

Review 6.  Fatty acid amide signaling molecules.

Authors:  Cyrine Ezzili; Katerina Otrubova; Dale L Boger
Journal:  Bioorg Med Chem Lett       Date:  2010-08-13       Impact factor: 2.823

7.  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

8.  A copper-catalyzed, pH-neutral construction of high-enantiopurity peptidyl ketones from peptidic s-acylthiosalicylamides in air at room temperature.

Authors:  Lanny S Liebeskind; Hao Yang; Hao Li
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

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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