Literature DB >> 16870439

Synthesis and SAR of conformationally restricted inhibitors of soluble epoxide hydrolase.

Paul D Jones1, Hsing-Ju Tsai, Zung N Do, Christophe Morisseau, Bruce D Hammock.   

Abstract

A series of conformationally restricted inhibitors of human soluble epoxide hydrolase (sEH) has been developed. Inhibition potency of the described compounds ranges from 4.2 microM to 1.1 nM against recombinant sEH. N-(1-Acetylpiperidin-4-yl)-N'-(adamant-1-yl) urea (5a) was found to be a potent inhibitor (IC(50) = 7.0 nM) that was also orally bioavailable in canines.

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Year:  2006        PMID： 16870439      PMCID： PMC1904344          DOI： 10.1016/j.bmcl.2006.07.009

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


  19 in total

Review 1.  Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings.

Authors:  C A Lipinski; F Lombardo; B W Dominy; P J Feeney
Journal:  Adv Drug Deliv Rev       Date:  2001-03-01       Impact factor: 15.470

2.  Soluble epoxide hydrolase regulates hydrolysis of vasoactive epoxyeicosatrienoic acids.

Authors:  Z Yu; F Xu; L M Huse; C Morisseau; A J Draper; J W Newman; C Parker; L Graham; M M Engler; B D Hammock; D C Zeldin; D L Kroetz
Journal:  Circ Res       Date:  2000-11-24       Impact factor: 17.367

3.  Structure of human epoxide hydrolase reveals mechanistic inferences on bifunctional catalysis in epoxide and phosphate ester hydrolysis.

Authors:  German A Gomez; Christophe Morisseau; Bruce D Hammock; David W Christianson
Journal:  Biochemistry       Date:  2004-04-27       Impact factor: 3.162

4.  Soluble epoxide hydrolase inhibition lowers arterial blood pressure in angiotensin II hypertension.

Authors:  John D Imig; Xueying Zhao; Jorge H Capdevila; Christophe Morisseau; Bruce D Hammock
Journal:  Hypertension       Date:  2002-02       Impact factor: 10.190

5.  QSAR and classification of murine and human soluble epoxide hydrolase inhibition by urea-like compounds.

Authors:  Nathan R McElroy; Peter C Jurs; Christophe Morisseau; Bruce D Hammock
Journal:  J Med Chem       Date:  2003-03-13       Impact factor: 7.446

Review 6.  Mammalian epoxide hydrases: inducible enzymes catalysing the inactivation of carcinogenic and cytotoxic metabolites derived from aromatic and olefinic compounds.

Authors:  F Oesch
Journal:  Xenobiotica       Date:  1973-05       Impact factor: 1.908

7.  Molecular properties that influence the oral bioavailability of drug candidates.

Authors:  Daniel F Veber; Stephen R Johnson; Hung-Yuan Cheng; Brian R Smith; Keith W Ward; Kenneth D Kopple
Journal:  J Med Chem       Date:  2002-06-06       Impact factor: 7.446

8.  Design, synthesis, and biological activity of 1,3-disubstituted ureas as potent inhibitors of the soluble epoxide hydrolase of increased water solubility.

Authors:  In-Hae Kim; Christophe Morisseau; Takaho Watanabe; Bruce D Hammock
Journal:  J Med Chem       Date:  2004-04-08       Impact factor: 7.446

Review 9.  Epoxyeicosatrienoic acids (EETs): metabolism and biochemical function.

Authors:  Arthur A Spector; Xiang Fang; Gary D Snyder; Neal L Weintraub
Journal:  Prog Lipid Res       Date:  2004-01       Impact factor: 16.195

10.  Design and synthesis of orally active benzamide derivatives as potent serotonin 4 receptor agonist.

Authors:  Shuji Sonda; Toshio Kawahara; Takahiro Murozono; Noriko Sato; Kiyoshi Asano; Keiichiro Haga
Journal:  Bioorg Med Chem       Date:  2003-09-15       Impact factor: 3.641
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  54 in total

Review 1.  Discovery of inhibitors of soluble epoxide hydrolase: a target with multiple potential therapeutic indications.

Authors:  Hong C Shen; Bruce D Hammock
Journal:  J Med Chem       Date:  2012-01-17       Impact factor: 7.446

2.  Design, synthesis and evaluation of non-urea inhibitors of soluble epoxide hydrolase.

Authors:  Stevan Pecic; Shi-Xian Deng; Christophe Morisseau; Bruce D Hammock; Donald W Landry
Journal:  Bioorg Med Chem Lett       Date:  2011-10-28       Impact factor: 2.823

3.  Inhibition of soluble epoxide hydrolase limits niacin-induced vasodilation in mice.

Authors:  Ahmet B Inceoglu; Heather L Clifton; Jun Yang; Christine Hegedus; Bruce D Hammock; Saul Schaefer
Journal:  J Cardiovasc Pharmacol       Date:  2012-07       Impact factor: 3.105

4.  Incorporation of piperazino functionality into 1,3-disubstituted urea as the tertiary pharmacophore affording potent inhibitors of soluble epoxide hydrolase with improved pharmacokinetic properties.

Authors:  Shao-Xu Huang; Hui-Yuan Li; Jun-Yan Liu; Christophe Morisseau; Bruce D Hammock; Ya-Qiu Long
Journal:  J Med Chem       Date:  2010-11-11       Impact factor: 7.446

5.  Solid-phase combinatorial approach for the optimization of soluble epoxide hydrolase inhibitors.

Authors:  Sung Hee Hwang; Christophe Morisseau; Zung Do; Bruce D Hammock
Journal:  Bioorg Med Chem Lett       Date:  2006-09-01       Impact factor: 2.823

6.  Cardioprotective effect of a dual acting epoxyeicosatrienoic acid analogue towards ischaemia reperfusion injury.

Authors:  S N Batchu; S B Lee; R S Qadhi; K R Chaudhary; H El-Sikhry; R Kodela; J R Falck; J M Seubert
Journal:  Br J Pharmacol       Date:  2011-02       Impact factor: 8.739

7.  Salicylate-urea-based soluble epoxide hydrolase inhibitors with high metabolic and chemical stabilities.

Authors:  Takeo Kasagami; In-Hae Kim; Hsing-Ju Tsai; Kosuke Nishi; Bruce D Hammock; Christophe Morisseau
Journal:  Bioorg Med Chem Lett       Date:  2009-01-27       Impact factor: 2.823

8.  Bioisosteric substitution of adamantane with bicyclic lipophilic groups improves water solubility of human soluble epoxide hydrolase inhibitors.

Authors:  Vladimir Burmistrov; Christophe Morisseau; Dmitry Karlov; Dmitry Pitushkin; Andrey Vernigora; Elena Rasskazova; Gennady M Butov; Bruce D Hammock
Journal:  Bioorg Med Chem Lett       Date:  2020-07-24       Impact factor: 2.823

9.  Structure-activity relationships of substituted oxyoxalamides as inhibitors of the human soluble epoxide hydrolase.

Authors:  In-Hae Kim; In-Hee Lee; Hisashi Nishiwaki; Bruce D Hammock; Kosuke Nishi
Journal:  Bioorg Med Chem       Date:  2014-01-03       Impact factor: 3.641

Review 10.  The 2014 Bernard B. Brodie award lecture-epoxide hydrolases: drug metabolism to therapeutics for chronic pain.

Authors:  Sean D Kodani; Bruce D Hammock
Journal:  Drug Metab Dispos       Date:  2015-03-11       Impact factor: 3.922
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