Synthesis of compounds with dioxabicyclo[3.3.1]nonane core
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2017-03-22
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Jaén: Universidad de Jaén
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[ES]En este Trabajo Fin de Grado (TFG) se ha llevado a cabo la síntesis, purificación y caracterización estructural de diez compuestos con esqueleto de 2,8-dioxabiciclo[3.3.1]nonano. Este TFG forma parte de un trabajo de investigación, que está realizándose en la Universidad de Jaén, sobre síntesis de este tipo de biciclos, evaluación de la actividad inhibitoria de LDH y estudio de la relación estructura-actividad. La síntesis de estos compuestos se ha conseguido mediante una reacción de adición nucleofílica de floroglucinol o resorcinol sobre sales de flavilio. Estas sales de flavilio también se han sintetizado en el presente TFG mediante condensación aldólica de 3',4'-diacetilacetofenona y salicilaldehído o derivados. La purificación de los compuestos sintetizados ha requerido el empleo de técnicas como la cromatografía en columna y HPLC semipreparativo. Por último, la determinación estructural se ha realizado haciendo uso de diferentes técnicas espectroscópicas.
[EN]The synthesis, purification and structural characterization of ten compounds with 2,8- dioxabicyclo[3.3.1]nonane core has been carried out in this final degree project. This work is part of a research project that is under development at the University of Jélén, about this kind of bicyclic compounds, their inhibitory activity of LDH and the relationship between the structure and the activity. The synthesis of these bicyclic compounds has been achieved by a nucleophilic attack of phloroglucinol or resorcinol to the flavylium salt. These flavylium salts have been also synthesised by an aldolic condensation of the 3',4'-diacetoxyacetophenone and salicylaldehyde or its derivatives. The purification was achieved by column chromatography or by semipreparative HPLC, and the structural characterization was done by different spectroscopic techniques.
[EN]The synthesis, purification and structural characterization of ten compounds with 2,8- dioxabicyclo[3.3.1]nonane core has been carried out in this final degree project. This work is part of a research project that is under development at the University of Jélén, about this kind of bicyclic compounds, their inhibitory activity of LDH and the relationship between the structure and the activity. The synthesis of these bicyclic compounds has been achieved by a nucleophilic attack of phloroglucinol or resorcinol to the flavylium salt. These flavylium salts have been also synthesised by an aldolic condensation of the 3',4'-diacetoxyacetophenone and salicylaldehyde or its derivatives. The purification was achieved by column chromatography or by semipreparative HPLC, and the structural characterization was done by different spectroscopic techniques.