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  • About
  • The Global ETD Search service is a free service for researchers to find electronic theses and dissertations. This service is provided by the Networked Digital Library of Theses and Dissertations.
    Our metadata is collected from universities around the world. If you manage a university/consortium/country archive and want to be added, details can be found on the NDLTD website.
1

Síntesis de derivados de ácidos y aminoácidos organoboronatos con potencial actividad inhibitoria hacia arginasas

Agüero Gaete, Francisco Andrés January 2017 (has links)
Memoria para optar al título de Químico / En este trabajo se estudió la síntesis de moléculas de estructura semejante al ácido 2(S)-amino-6-boronohexanoico (ABH), que al igual que este último pudieran tener algún efecto en la inhibición de la enzima arginasa, buscando una ruta sintética que utilice reactivos más económicos. Usando dos materiales de partida distintos, malonato de dietilo y N-(difenilmetilen)glicinato de etilo, se probaron diferentes condiciones para la alquilación con bromuro de alilo y 1- bromo-4-buteno, de modo de obtener ABH racémico, el homólogo inferior de ABH, y ácido 6-boronohexanoico, que no contiene el grupo amino. La hidroboración subsiguiente se ensayó de acuerdo a dos metodologías: reacción directa de adición de catecolborano, y adición de pinacolborano catalizada por una sal de iridio. La síntesis resultó más conveniente por el segundo método. Para acceder al producto final se realizó una hidrólisis y descarboxilación / In this work, the synthesis of a set of molecules with structures similar to that of 2-(S)-amino-6-boronohexanoic acid (ABH), with potentially similar effect in arginase enzyme inhibition, looking for a synthetic route that uses cheaper reagents, was studied. Using two different starting materials, diethyl malonate and ethyl N-(diphenylmethylene)glycinate, several conditions for their alkylation with allyl bromide and 1-bromo-4-butene were tested, in order to obtain racemic ABH, its lower homolog, and 6-boronohexanoic acid, lacking an amino group. The subsequent hydroboration was attempted using two different methods: direct addition of catecholborane, and an iridium salt-catalyzed addition of pinacolborane. The synthesis was more convenient by the second method. In order to obtain the final product, a hydrolysis and decarboxylation was held / FONDEF D11/1098

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