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dc.contributor.authorBermejo, Almudena
dc.contributor.authorBarrachina, Isabel
dc.contributor.authorEl Aouad, Noureddine
dc.contributor.authorFranck, Xavier
dc.contributor.authorChahboune, Nadia
dc.contributor.authorAndreu, Inmaculada
dc.contributor.authorFigadère, Bruno
dc.contributor.authorVila, Laura
dc.contributor.authorhennuyer, Nathalie
dc.contributor.authorStaels, Bart
dc.contributor.authorDacquet, Catherine
dc.contributor.authorCaignard, Daniel H.
dc.contributor.authorSanz, María-Jesús
dc.contributor.authorCortés, Diego
dc.contributor.authorCabedo, Nuria
dc.date.accessioned2020-05-25T17:14:10Z
dc.date.available2020-05-25T17:14:10Z
dc.date.issued2019
dc.identifier.citationBermejo, A., Barrachina, I., El Aouad, N., Franck, X., Chahboune, N., Andreu, I., ... & Dacquet, C. (2019). Synthesis of benzopyran derivatives as PPARα and/or PPARγ activators. Bioorganic & medicinal chemistry, 27(24), 115162.
dc.identifier.issn0968-0896
dc.identifier.urihttp://hdl.handle.net/20.500.11939/6461
dc.description.abstractWe describe the synthesis of 26 compounds, small polycerasoidol analogs, that are Lipinski’s rule-of-five compliant. In order to confirm key structural features to activate PPARα and/or PPARγ, we have adopted structural modifications in the following parts: (i) the benzopyran core (hydrophobic nucleus) by benzopyran-4-one, dihydrobenzopyran or benzopyran-4-ol; (ii) the side chain at 2-position by shortening to C3, C4 and C5-carbons versus C-9-carbons of polycerasoidol; (iii) the carboxylic group (polar head) by oxygenated groups (hydroxyl, acetoxy, epoxide, ester, aldehyde) or non-oxygenated motifs (allyl and alkyl). Benzopyran-4-ones 6, 12, 13 and 17 as well as dihydrobenzopyrans 22, 24 and 25 were able to activate hPPARα, whereas benzopyran-4-one (7) with C5-carbons in the side chain exhibited hPPARγ agonism. According to our previous docking studies, SAR confirm that the hydrophobic nucleus (benzopyran-4-one or dihydrobenzopyran) is essential to activate PPARα and/or PPARγ, and the flexible linker (side alkyl chain) should containg at least C5-carbon atoms to activate PPARγ. By contrast, the polar head (“carboxylic group”) tolerated several oxygenated groups but also non-oxygenated motifs. Taking into account these key structural features, small polycerasoidol analogs might provide potential active molecules useful in the treatment of dyslipidemia and/or type 2 diabetes.es
dc.language.isoenes
dc.publisherElsevieres
dc.rightsAtribución-NoComercial-SinDerivadas 3.0 España*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/es/*
dc.subjectPolycerasoidoles
dc.subjectPPARα agonismes
dc.subjectPPARγ agonismes
dc.titleSynthesis of benzopyran derivatives as PPARα and/or PPARγ activatorses
dc.typearticlees
dc.authorAddressInstituto Valenciano de Investigaciones Agrarias (IVIA), Carretera CV-315, Km. 10’7, 46113 Moncada (Valencia), Españaes
dc.entidadIVIACentro de Citricultura y Producción Vegetales
dc.identifier.doi10.1016/j.bmc.2019.115162es
dc.identifier.urlhttps://www.sciencedirect.com/science/article/pii/S0968089619316505es
dc.journal.issueNumber24es
dc.journal.titleBioorganic & Medicinal Chemistryes
dc.journal.volumeNumber27es
dc.page.final115162es
dc.page.initial115162es
dc.source.typeelectronicoes
dc.subject.agrisF60 Plant physiology and biochemistryes
dc.subject.agrovocBenzopyrenees
dc.type.hasVersiondraftes


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