Reacción de acoplamiento de Suzuki-Miyaura entre iminas halogenadas y ácidos borónicos
Fecha
2024-09-06
Autores
Título de la revista
ISSN de la revista
Título del volumen
Editor
Resumen
La hiperoxaluria primaria tipo 1 (PH-1) es una enfermedad rara causada por la mutación del gen AGXT que trae como consecuencia la sobreproducción nociva de oxalato en el organismo. Una posible terapia consiste en el empleo de inhibidores de la enzima lactato deshidrogenasa (LDH). En este TFG se pretende iniciar la ruta sintética de una familia de potenciales inhibidores de LDH, llevando a cabo la reacción de acoplamiento de Suzuki-Miyaura entre varios haloarenos (conteniendo un grupo imino) y un ácido fenilborónico (4). Los haloarenos de partida (3a-3d) se han preparado eficazmente a partir de una anilina sustituida (1) y varios halo-aldehídos (2a-2d), y la reacción de acoplamiento, conducente al compuesto 5, se ha dado aceptablemente bien cuando el halógeno del haloareno es bromo o yodo. Los compuestos sintetizados se han purificado por recristalización o por cromatografía flash y se han caracterizado por RMN. Dos de los compuestos sintetizados (3d, 5) se describen por primera vez en este TFG.
Primary hyperoxaluria type 1 (PH-1) is a rare disease caused by a mutation in the AGXT gene, resulting in harmful overproduction of oxalate in the human body. A possible therapy involves the use of lactate dehydrogenase (LDH) enzyme inhibitors. This Final Degree Project aims to initiate the synthetic route of family of potential LDH inhibitors by carrying out the Suzuki-Miyaura coupling reaction between various haloarenes (containing an imino group) and a phenylboronic acid (4). The starting haloarenes (3a-3d) have been effectively prepared from a substituted aniline (1) and several halo-aldehydes (2a-2d), and the coupling reaction leading to compound 5 has been reasonably successful when the halogen in the haloarene is bromine or iodine. The synthesized compounds have been purified by recrystallization or flash chromatography and characterized by NMR. Two of the synthesized compounds (3d, 5) are described for the first time in this Final Degree Project.
Primary hyperoxaluria type 1 (PH-1) is a rare disease caused by a mutation in the AGXT gene, resulting in harmful overproduction of oxalate in the human body. A possible therapy involves the use of lactate dehydrogenase (LDH) enzyme inhibitors. This Final Degree Project aims to initiate the synthetic route of family of potential LDH inhibitors by carrying out the Suzuki-Miyaura coupling reaction between various haloarenes (containing an imino group) and a phenylboronic acid (4). The starting haloarenes (3a-3d) have been effectively prepared from a substituted aniline (1) and several halo-aldehydes (2a-2d), and the coupling reaction leading to compound 5 has been reasonably successful when the halogen in the haloarene is bromine or iodine. The synthesized compounds have been purified by recrystallization or flash chromatography and characterized by NMR. Two of the synthesized compounds (3d, 5) are described for the first time in this Final Degree Project.