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Identifier uch.chemistry.msc//2004hatzakis
Title Σύνθεση πολικών/υδατοδιαλυτών παραγώγων της ανθελονοσιακής ένωσης ασκαριδόλη
Alternative Title Synthesis of polar/water soluble derivatives of the antimalarial ascaridol
Creator Hatzakis, Manolis
Abstract Ascaridole a monoterpene natural product (endoperoxide of α-terpinene) has weak antimalarial properties against malaria parasites. However, its reactivity in vitro is comparable to the currently used drug artemisinin. This may be attributed to is high lipophilicity. We attempted to develop a new methodology for the synthesis of polar ascaridole derivatives for in vivo antimalarial studies. By using as a “key-step” the selective rearrangement of the natural products nopol, methyl nopoate, perillyl aldehyde and methyl perillate, promoted by zeolite Na-Y, we prepared a series of polar conjugated 1,3-cyclohexadienes, which are precursors to the endoperoxides. The rearrangement protocol is a novel methodoly and is moderate to highly selective depending on the substate. The polar cyclohexadienes were photooxygenated (reaction with 1Ο2) to produce nearly quantitatively a series of ascaridole-type endoperoxides. The structure-biological activity relationship will shed new light to the synthesis of new antimalarial compounds.
Issue date 2004-07-01
Date available 2004-07-27
Collection   School/Department--School of Sciences and Engineering--Department of Chemistry--Post-graduate theses
  Type of Work--Post-graduate theses
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