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Identifier 000397565
Title Σύνθεση και μελέτη δομής – δραστικότητας παραγώγων του κοστικού οξέος κατά της δράσης της VARROA DESTRUCTOR στην ευρωπαϊκή μέλισσα APIS MELLIFERA
Alternative Title Synthesis and structure - activity relationship studies of costic acid derivatives against the action of VARROA DESTRUCTOR on the european bee APIS MELLIFERA
Author Γεωργιλαδάκη, Σοφία Α.
Thesis advisor Κατερινόπουλος, Χαράλαμπος Ε.
Reviewer Παπαχατζής, Δημήτριος
Βασιλικογιαννάκης, Γεώργιος
Ορφανόπουλος, Μιχαήλ
Στρατάκης, Εμμανουήλ
Σμόνου, Ιουλία
Σπύρος, Απόστολος
Abstract In this thesis, the design, synthesis and biological activity studies of a series of costic acid analogs is described. Costic acid is a sesquiterpene-type monocarboxylic acid which has been isolated from the plant Dittrichia Viscosa, known to the local population by the common name ‘Ακονιζα’ (Aconiza). Recent studies have shown that costic acid acts as an acaricide against a bee parasite known as Varroa Destructor. In an effort to synthesize costic acid analogs with activity greater than that of the parent compound and considering the information that some diacids such as oxalic acid act as acaricides against V. Destructor, a series of costic acid congeners were designed, synthesized and studied for biological activiy. These compounds contain the costic acid decalin carbon framework connected to dicarboxylic side chains. The first synthetic approach is focused on the synthesis of malonic acid derivatives using the of malonic synthesis methodology. The synthetic routes that were selected using as starting materials beta-tetralone or decalone systems were not particularly successful, giving either side products or the desired analogs in very small yields. The second synthetic approach includes the synthesis of of succinic acid derivatives that were connected to the decalin skeleton under Stobbe reaction conditions. This methodology proved to be particularly successful, yielding a number of analogs and resulting in the preparation of 2-[(2R,4aR,8aR)-4a-methyldecahydro-2-naphthalenyl]butanedioic acid, wherein the desired enantioselectivity was achieved in the construction of the three stereogenic centres in the decalin skeleton of the molecule. In order to define the pharmacophore part of costic acid, the synthesized analogs were tested for acaricidal activity against the V. destructor. The results are analyzed in terms of the structure-activity relationship studies of these analogs.
Language Greek
Subject Aντίδραση Stobbe
Dittrichia viscosa
Stobbe reaction
Κοστικό οξύ
Issue date 2015-11-09
Collection   Faculty/Department--Faculty of Sciences and Engineering--Department of Chemistry--Doctoral theses
  Type of Work--Doctoral theses
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