Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Symmetric adamantyl-diureas as soluble epoxide hydrolase inhibitors.

Literature DB >> 24685540

Symmetric adamantyl-diureas as soluble epoxide hydrolase inhibitors.

Vladimir Burmistrov¹, Christophe Morisseau², Kin Sing Stephen Lee², Diyala S Shihadih², Todd R Harris², Gennady M Butov¹, Bruce D Hammock³.

Abstract

A series of inhibitors of the soluble epoxide hydrolase (sEH) containing two urea groups has been developed. Inhibition potency of the described compounds ranges from 2.0 μM to 0.4 nM. 1,6-(Hexamethylene)bis[(adamant-1-yl)urea] (3b) was found to be a potent slow tight binding inhibitor (IC50=0.5 nM) with a strong binding to sEH (Ki=3.1 nM) and a moderately long residence time on the enzyme (koff=1.05 × 10(-3) s(-1); t1/2=11 min).

Entities: Chemical Disease Gene Species

Keywords: Adamantane; Diurea; Inhibitor; Isocyanate; Soluble epoxide hydrolase

Mesh：

Substances：

Year: 2014 PMID： 24685540 PMCID： PMC4019751 DOI： 10.1016/j.bmcl.2014.03.016

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

26 in total

1. A common mechanism underlying promiscuous inhibitors from virtual and high-throughput screening.

Authors: Susan L McGovern; Emilia Caselli; Nikolaus Grigorieff; Brian K Shoichet
Journal: J Med Chem Date: 2002-04-11 Impact factor: 7.446

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. An orally active epoxide hydrolase inhibitor lowers blood pressure and provides renal protection in salt-sensitive hypertension.

Authors: John D Imig; Xueying Zhao; Constantine Z Zaharis; Jeffrey J Olearczyk; David M Pollock; John W Newman; In-Hae Kim; Takaho Watanabe; Bruce D Hammock
Journal: Hypertension Date: 2005-09-12 Impact factor: 10.190

4. Fluorescent substrates for soluble epoxide hydrolase and application to inhibition studies.

Authors: Paul D Jones; Nicola M Wolf; Christophe Morisseau; Paul Whetstone; Bertold Hock; Bruce D Hammock
Journal: Anal Biochem Date: 2005-08-01 Impact factor: 3.365

5. 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

6. Structural refinement of inhibitors of urea-based soluble epoxide hydrolases.

Authors: Christophe Morisseau; Marvin H Goodrow; John W Newman; Craig E Wheelock; Deanna L Dowdy; Bruce D Hammock
Journal: Biochem Pharmacol Date: 2002-05-01 Impact factor: 5.858

Review 7. Vascular protective effects of cytochrome p450 epoxygenase-derived eicosanoids.

Authors: Martin Spiecker; James K Liao
Journal: Arch Biochem Biophys Date: 2005-01-15 Impact factor: 4.013

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

9. Discovery of 2,8-diazaspiro[4.5]decane-based trisubstituted urea derivatives as highly potent soluble epoxide hydrolase inhibitors and orally active drug candidates for treating hypertension.

Authors: Yuko Kato; Nobuhiro Fuchi; Hajime Saburi; Yutaka Nishimura; Ayano Watanabe; Mai Yagi; Yasuhito Nakadera; Eriko Higashi; Masateru Yamada; Takumi Aoki
Journal: Bioorg Med Chem Lett Date: 2013-08-20 Impact factor: 2.823

Review 10. Eicosanoids and renal damage in cardiometabolic syndrome.

Authors: John D Imig
Journal: Expert Opin Drug Metab Toxicol Date: 2008-02 Impact factor: 4.481

8 in total

1. Effects of adamantane alterations on soluble epoxide hydrolase inhibition potency, physical properties and metabolic stability.

Authors: Vladimir Burmistrov; Christophe Morisseau; Todd R Harris; Gennady Butov; Bruce D Hammock
Journal: Bioorg Chem Date: 2017-12-30 Impact factor: 5.275

2. Imidazolidine-2,4,5- and pirimidine-2,4,6-triones - New primary pharmacophore for soluble epoxide hydrolase inhibitors with enhanced water solubility.

Authors: Vladimir Burmistrov; Christophe Morisseau; Vladimir D'yachenko; Dmitry Karlov; Gennady M Butov; Bruce D Hammock
Journal: Bioorg Med Chem Lett Date: 2019-12-18 Impact factor: 2.823

3. Exploring the size of the lipophilic unit of the soluble epoxide hydrolase inhibitors.

Authors: Sandra Codony; Elena Valverde; Rosana Leiva; José Brea; M Isabel Loza; Christophe Morisseau; Bruce D Hammock; Santiago Vázquez
Journal: Bioorg Med Chem Date: 2019-08-26 Impact factor: 3.641

4. Identification of potent inhibitors of the chicken soluble epoxide hydrolase.

Authors: Diyala S Shihadih; Todd R Harris; Jun Yang; Oleg Merzlikin; Kin Sing S Lee; Bruce D Hammock; Christophe Morisseau
Journal: Bioorg Med Chem Lett Date: 2014-11-26 Impact factor: 2.823

5. 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