Literature DB >> 23237835

Synthesis and structure-activity relationship of piperidine-derived non-urea soluble epoxide hydrolase inhibitors.

Stevan Pecic1, Svetlana Pakhomova, Marcia E Newcomer, Christophe Morisseau, Bruce D Hammock, Zhengxiang Zhu, Alison Rinderspacher, Shi-Xian Deng.   

Abstract

A series of potent amide non-urea inhibitors of soluble epoxide hydrolase (sEH) is disclosed. The inhibition of soluble epoxide hydrolase leads to elevated levels of epoxyeicosatrienoic acids (EETs), and thus inhibitors of sEH represent one of a novel approach to the development of vasodilatory and anti-inflammatory drugs. Structure-activities studies guided optimization of a lead compound, identified through high-throughput screening, gave rise to sub-nanomolar inhibitors of human sEH with stability in human liver microsomal assay suitable for preclinical development. Published by Elsevier Ltd.

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Year:  2012        PMID： 23237835      PMCID： PMC3541548          DOI： 10.1016/j.bmcl.2012.11.084

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


  19 in total

1.  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

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

Review 3.  Emerging role of epoxyeicosatrienoic acids in coronary vascular function.

Authors:  B T Larsen; D D Gutterman; O A Hatoum
Journal:  Eur J Clin Invest       Date:  2006-05       Impact factor: 4.686

4.  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

5.  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

6.  Novel epoxides formed during the liver cytochrome P-450 oxidation of arachidonic acid.

Authors:  N Chacos; J R Falck; C Wixtrom; J Capdevila
Journal:  Biochem Biophys Res Commun       Date:  1982-02-11       Impact factor: 3.575

Review 7.  Soluble epoxide hydrolase inhibitors: a patent review.

Authors:  Hong C Shen
Journal:  Expert Opin Ther Pat       Date:  2010-07       Impact factor: 6.674

Review 8.  Soluble epoxide hydrolase, a target with multiple opportunities for cardiovascular drug discovery.

Authors:  Joseph P Marino
Journal:  Curr Top Med Chem       Date:  2009       Impact factor: 3.295

Review 9.  Soluble epoxide hydrolase as a therapeutic target for cardiovascular diseases.

Authors:  John D Imig; Bruce D Hammock
Journal:  Nat Rev Drug Discov       Date:  2009-10       Impact factor: 84.694

10.  Discovery of potent non-urea inhibitors of soluble epoxide hydrolase.

Authors:  Yuli Xie; Yidong Liu; Gangli Gong; Deborah H Smith; Fang Yan; Alison Rinderspacher; Yan Feng; Zhengxiang Zhu; Xiangpo Li; Shi-Xian Deng; Lars Branden; Dusica Vidović; Caty Chung; Stephan Schürer; Christophe Morisseau; Bruce D Hammock; Donald W Landry
Journal:  Bioorg Med Chem Lett       Date:  2008-09-20       Impact factor: 2.823
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  11 in total

1.  Symmetric adamantyl-diureas as soluble epoxide hydrolase inhibitors.

Authors:  Vladimir Burmistrov; Christophe Morisseau; Kin Sing Stephen Lee; Diyala S Shihadih; Todd R Harris; Gennady M Butov; Bruce D Hammock
Journal:  Bioorg Med Chem Lett       Date:  2014-03-20       Impact factor: 2.823

2.  Investigation of the binding mode of 1, 3, 4-oxadiazole derivatives as amide-based inhibitors for soluble epoxide hydrolase (sEH) by molecular docking and MM-GBSA.

Authors:  Leila Karami; Ali Akbar Saboury; Elham Rezaee; Sayyed Abbas Tabatabai
Journal:  Eur Biophys J       Date:  2016-12-07       Impact factor: 1.733

3.  Stacking with No Planarity?

Authors:  Hakan Gunaydin; Michael D Bartberger
Journal:  ACS Med Chem Lett       Date:  2016-04-06       Impact factor: 4.345

4.  Novel piperidine-derived amide sEH inhibitors as mediators of lipid metabolism with improved stability.

Authors:  Stevan Pecic; Amir A Zeki; Xiaoming Xu; Gina Y Jin; Shuwei Zhang; Sean Kodani; Marlin Halim; Christophe Morisseau; Bruce D Hammock; Shi-Xian Deng
Journal:  Prostaglandins Other Lipid Mediat       Date:  2018-03-20       Impact factor: 3.072

5.  Further exploration of the structure-activity relationship of dual soluble epoxide hydrolase/fatty acid amide hydrolase inhibitors.

Authors:  Stephanie Wilt; Sean Kodani; Leah Valencia; Paula K Hudson; Stephanie Sanchez; Taylor Quintana; Christophe Morisseau; Bruce D Hammock; Ram Kandasamy; Stevan Pecic
Journal:  Bioorg Med Chem       Date:  2021-11-11       Impact factor: 3.641

6.  Repositioning of Quinazolinedione-Based Compounds on Soluble Epoxide Hydrolase (sEH) through 3D Structure-Based Pharmacophore Model-Driven Investigation.

Authors:  Erica Gazzillo; Stefania Terracciano; Dafne Ruggiero; Marianna Potenza; Maria Giovanna Chini; Gianluigi Lauro; Katrin Fischer; Robert Klaus Hofstetter; Assunta Giordano; Oliver Werz; Ines Bruno; Giuseppe Bifulco
Journal:  Molecules       Date:  2022-06-16       Impact factor: 4.927

7.  Mutation of an atypical oxirane oxyanion hole improves regioselectivity of the α/β-fold epoxide hydrolase Alp1U.

Authors:  Liping Zhang; Bidhan Chandra De; Wenjun Zhang; Attila Mándi; Zhuangjie Fang; Chunfang Yang; Yiguang Zhu; Tibor Kurtán; Changsheng Zhang
Journal:  J Biol Chem       Date:  2020-10-01       Impact factor: 5.157

8.  Design, synthesis and biological evaluation of 4-benzamidobenzoic Acid hydrazide derivatives as novel soluble epoxide hydrolase inhibitors.

Authors:  Elham Rezaee Zavareh; Mahdi Hedayati; Laleh Hoghooghi Rad; Soraya Shahhosseini; Mehrdad Faizi; Sayyed Abbas Tabatabai
Journal:  Iran J Pharm Res       Date:  2014       Impact factor: 1.696

9.  Discovery of Novel Soluble Epoxide Hydrolase Inhibitors as Potent Vasodilators.

Authors:  Neetika Tripathi; Sarvesh Paliwal; Swapnil Sharma; Kanika Verma; Ritika Gururani; Akanksha Tiwari; Amrita Verma; Monika Chauhan; Aarti Singh; Dipak Kumar; Aditya Pant
Journal:  Sci Rep       Date:  2018-10-02       Impact factor: 4.379

10.  Dual Farnesoid X Receptor/Soluble Epoxide Hydrolase Modulators Derived from Zafirlukast.

Authors:  Simone Schierle; Moritz Helmstädter; Jurema Schmidt; Markus Hartmann; Maximiliane Horz; Astrid Kaiser; Lilia Weizel; Pascal Heitel; Anna Proschak; Victor Hernandez-Olmos; Ewgenij Proschak; Daniel Merk
Journal:  ChemMedChem       Date:  2019-11-19       Impact factor: 3.466
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