Literature DB >> 19216074

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

Takeo Kasagami1, In-Hae Kim, Hsing-Ju Tsai, Kosuke Nishi, Bruce D Hammock, Christophe Morisseau.   

Abstract

We investigated N-adamantyl-N'-phenyl urea derivatives as simple sEH inhibitors. Salicylate ester derivatives have high inhibitory activities against human sEH, while the free benzoic acids are less active. The methyl salicylate derivative is a potent sEH inhibitor, which also has high metabolic and chemical stabilities; suggesting that such inhibitors are potential lead molecule for bioactive compounds acting in vivo.

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Year:  2009        PMID: 19216074      PMCID: PMC2900318          DOI: 10.1016/j.bmcl.2009.01.069

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


  30 in total

1.  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

2.  Human soluble epoxide hydrolase: structural basis of inhibition by 4-(3-cyclohexylureido)-carboxylic acids.

Authors:  German A Gomez; Christophe Morisseau; Bruce D Hammock; David W Christianson
Journal:  Protein Sci       Date:  2005-12-01       Impact factor: 6.725

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

Authors:  Paul D Jones; Hsing-Ju Tsai; Zung N Do; Christophe Morisseau; Bruce D Hammock
Journal:  Bioorg Med Chem Lett       Date:  2006-07-25       Impact factor: 2.823

4.  Design of bioavailable derivatives of 12-(3-adamantan-1-yl-ureido)dodecanoic acid, a potent inhibitor of the soluble epoxide hydrolase.

Authors:  In-Hae Kim; Kosuke Nishi; Hsing-Ju Tsai; Tanya Bradford; Yasuko Koda; Takaho Watanabe; Christophe Morisseau; Joanne Blanchfield; Istvan Toth; Bruce D Hammock
Journal:  Bioorg Med Chem       Date:  2006-09-29       Impact factor: 3.641

5.  Substrate specificity of carboxylesterase isozymes and their contribution to hydrolase activity in human liver and small intestine.

Authors:  Teruko Imai; Megumi Taketani; Mayumi Shii; Masakiyo Hosokawa; Kan Chiba
Journal:  Drug Metab Dispos       Date:  2006-07-12       Impact factor: 3.922

6.  Substituted adamantyl-urea inhibitors of the soluble epoxide hydrolase dilate mesenteric resistance vessels.

Authors:  Jeffrey J Olearczyk; Mary B Field; In-Hae Kim; Christophe Morisseau; Bruce D Hammock; John D Imig
Journal:  J Pharmacol Exp Ther       Date:  2006-06-13       Impact factor: 4.030

7.  Enhancement of antinociception by coadministration of nonsteroidal anti-inflammatory drugs and soluble epoxide hydrolase inhibitors.

Authors:  Kara R Schmelzer; Bora Inceoglu; Lukas Kubala; In-Hae Kim; Steven L Jinks; Jason P Eiserich; Bruce D Hammock
Journal:  Proc Natl Acad Sci U S A       Date:  2006-09-01       Impact factor: 11.205

8.  Peptidyl-urea based inhibitors of soluble epoxide hydrolases.

Authors:  Christophe Morisseau; John W Newman; Hsing-Ju Tsai; Preston A Baecker; Bruce D Hammock
Journal:  Bioorg Med Chem Lett       Date:  2006-10-15       Impact factor: 2.823

9.  Orally bioavailable potent soluble epoxide hydrolase inhibitors.

Authors:  Sung Hee Hwang; Hsing-Ju Tsai; Jun-Yan Liu; Christophe Morisseau; Bruce D Hammock
Journal:  J Med Chem       Date:  2007-07-06       Impact factor: 7.446

10.  Increasing or stabilizing renal epoxyeicosatrienoic acid production attenuates abnormal renal function and hypertension in obese rats.

Authors:  Hui Huang; Christophe Morisseau; JingFeng Wang; Tianxin Yang; John R Falck; Bruce D Hammock; Mong-Heng Wang
Journal:  Am J Physiol Renal Physiol       Date:  2007-04-18
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  8 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.  Pharmacokinetic screening of soluble epoxide hydrolase inhibitors in dogs.

Authors:  Hsing-Ju Tsai; Sung Hee Hwang; Christophe Morisseau; Jun Yang; Paul D Jones; Takeo Kasagami; In-Hae Kim; Bruce D Hammock
Journal:  Eur J Pharm Sci       Date:  2010-03-30       Impact factor: 4.384

3.  The structure-activity relationship of urea derivatives as anti-tuberculosis agents.

Authors:  Joshua R Brown; Elton J North; Julian G Hurdle; Christophe Morisseau; Jerrod S Scarborough; Dianqing Sun; Jana Korduláková; Michael S Scherman; Victoria Jones; Anna Grzegorzewicz; Rebecca M Crew; Mary Jackson; Michael R McNeil; Richard E Lee
Journal:  Bioorg Med Chem       Date:  2011-07-24       Impact factor: 3.641

4.  Screening a library of 1600 adamantyl ureas for anti-Mycobacterium tuberculosis activity in vitro and for better physical chemical properties for bioavailability.

Authors:  Michael S Scherman; Elton J North; Victoria Jones; Tamara N Hess; Anna E Grzegorzewicz; Takeo Kasagami; In-Hae Kim; Oleg Merzlikin; Anne J Lenaerts; Richard E Lee; Mary Jackson; Christophe Morisseau; Michael R McNeil
Journal:  Bioorg Med Chem       Date:  2012-03-31       Impact factor: 3.641

5.  Structure-activity relationships of cycloalkylamide derivatives as inhibitors of the soluble epoxide hydrolase.

Authors:  In-Hae Kim; Yong-Kyu Park; Bruce D Hammock; Kosuke Nishi
Journal:  J Med Chem       Date:  2011-02-21       Impact factor: 7.446

6.  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

7.  Biologically active ester derivatives as potent inhibitors of the soluble epoxide hydrolase.

Authors:  In-Hae Kim; Kosuke Nishi; Takeo Kasagami; Christophe Morisseau; Jun-Yan Liu; Hsing-Ju Tsai; Bruce D Hammock
Journal:  Bioorg Med Chem Lett       Date:  2012-08-02       Impact factor: 2.823

8.  Synthesis and biological evaluation of sorafenib- and regorafenib-like sEH inhibitors.

Authors:  Sung Hee Hwang; Aaron T Wecksler; Guodong Zhang; Christophe Morisseau; Long V Nguyen; Samuel H Fu; Bruce D Hammock
Journal:  Bioorg Med Chem Lett       Date:  2013-05-15       Impact factor: 2.823

  8 in total

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