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dc.contributor.authorCheng Sánchez, Iván
dc.contributor.authorSarabia, Francisco
dc.date.accessioned2017-07-20T09:44:46Z
dc.date.available2017-07-20T09:44:46Z
dc.date.created2017
dc.date.issued2017-07-20
dc.identifier.urihttp://hdl.handle.net/10630/14280
dc.description.abstract(-)-Depudecin (1), isolated from the culture broths of the fungus Alternaria brassicicola [1], has been identified as a selective inhibitor of histone deacetylases (HDAC) with an IC50 in the low μM range. In contrast to representative HDAC inhibitors, depudecin represents a unique inhibitor of these enzymes by virtue of its molecular structure, featuring the presence of two oxirane rings separated by a trans double bond. Originally discovered as part of a biological screen directed towards the identification of antitumour agents with detransforming activity [2], depudecin was identified as a bioactive metabolite capable of reverting the transformed morphology of tumor cells. Depudecin induced cell cycle arrest and cellular differentiation [3], and also exhibited anti-angiogenesis activity [4]. Prompted by its striking biological properties and enticing structure, we decided to initiate a research program directed towards the synthesis of natural depudecin which has recently culminated with a linear total synthesis [5]. In order to develop an improved access to natural depudecin and analogues for further biological screenings, we explored a synthetic alternative as a shorter and more convergent approach. In this communication we report a new total synthesis of the natural product (-)-depudecin. A key feature of the synthesis is the utilization of an olefin cross-metathesis strategy, which provides for an efficient and improved access to natural depudecin. This strategy was applied to the preparation of the 10-epi and (+)-depudecin, which represent interesting stereoisomeric analogues for SAR studies.es_ES
dc.description.sponsorshipUniversidad de Málaga. Campus de Excelencia Internacional Andalucía Tech.es_ES
dc.language.isoenges_ES
dc.rightsinfo:eu-repo/semantics/openAccesses_ES
dc.subjectAntineoplásicoses_ES
dc.subject.otherTotal synthesises_ES
dc.subject.otherNatural productses_ES
dc.subject.otherAntitumor Agentses_ES
dc.subject.otherDepudecines_ES
dc.titleTotal synthesis of depudecin and analogues via an olefin cross-metathesis based strategyes_ES
dc.typeinfo:eu-repo/semantics/conferenceObjectes_ES
dc.centroFacultad de Cienciases_ES
dc.relation.eventtitle20th European Symposium on Organic Chemistry (ESOC 17)es_ES
dc.relation.eventplaceColonia, Alemaniaes_ES
dc.relation.eventdateJulio, 2017es_ES
dc.identifier.orcidhttp://orcid.org/X0000-0002-5149-3576es_ES
dc.cclicenseby-nc-ndes_ES


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