JavaScript is disabled for your browser. Some features of this site may not work without it.

    Listar

    Todo RIUMAComunidades & ColeccionesPor fecha de publicaciónAutoresTítulosMateriasTipo de publicaciónCentrosEsta colecciónPor fecha de publicaciónAutoresTítulosMateriasTipo de publicaciónCentros

    Mi cuenta

    AccederRegistro

    Estadísticas

    Ver Estadísticas de uso

    DE INTERÉS

    Datos de investigaciónReglamento de ciencia abierta de la UMAPolítica de RIUMAPolitica de datos de investigación en RIUMASHERPA/RoMEODulcinea
    Preguntas frecuentesManual de usoDerechos de autorContacto/Sugerencias
    Ver ítem 
    •   RIUMA Principal
    • Investigación
    • Química Orgánica - (QO)
    • QO - Contribuciones a congresos científicos
    • Ver ítem
    •   RIUMA Principal
    • Investigación
    • Química Orgánica - (QO)
    • QO - Contribuciones a congresos científicos
    • Ver ítem

    Total synthesis of depudecin and analogues via an olefin cross-metathesis based strategy

    • Autor
      Cheng-Sánchez, Iván; Sarabia-García, Francisco RamónAutoridad Universidad de Málaga
    • Fecha
      2017-07-20
    • Palabras clave
      Antineoplásicos
    • Resumen
      (-)-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.
    • URI
      http://hdl.handle.net/10630/14280
    • Compartir
      RefworksMendeley
    Mostrar el registro completo del ítem
    Ficheros
    Abstract_I. Cheng-Sánchez.pdf (61.51Kb)
    Colecciones
    • QO - Contribuciones a congresos científicos

    Estadísticas

    Ver Estadísticas de uso
    Buscar en Dimension
    REPOSITORIO INSTITUCIONAL UNIVERSIDAD DE MÁLAGA
    REPOSITORIO INSTITUCIONAL UNIVERSIDAD DE MÁLAGA
     

     

    REPOSITORIO INSTITUCIONAL UNIVERSIDAD DE MÁLAGA
    REPOSITORIO INSTITUCIONAL UNIVERSIDAD DE MÁLAGA