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Formación de indazol activada por nitrorreductasa

Henrik Terholsen1, Lisa Medema1, Elizaveta Chernyshova1

  • 1Department of Chemical and Pharmaceutical Biology, Groningen Research Institute of Pharmacy, University of Groningen, Groningen, The Netherlands.

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PubMed
Resumen
Este resumen es generado por máquina.

La síntesis enzimática de indazol ahora es posible utilizando enzimas nitrorreductasas. Este método biocatalítico convierte eficientemente derivados de nitrobenzilamina en valiosos compuestos de indazol, avanzando en la química sostenible.

Palabras clave:
biocatálisissíntesis orgánicaquímica medicinalindazolesnitrorreductasaquímica sostenible

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Área de la Ciencia:

  • Biocatálisis
  • Síntesis Orgánica
  • Química Medicinal

Sus antecedentes:

  • La biocatálisis ofrece rutas sintéticas sostenibles, pero carece de vías enzimáticas para muchas clases de compuestos, incluidos los indazoles.
  • Los indazoles son andamios importantes en el diseño de fármacos, sin embargo, las rutas de síntesis enzimática siguen estando poco desarrolladas.

Objetivo del estudio:

  • Desarrollar una nueva ruta enzimática para la formación de indazol utilizando enzimas nitrorreductasas.
  • Explorar el alcance y las limitaciones de este enfoque biocatalítico para la síntesis de diversos derivados de indazol.

Principales métodos:

  • Se utilizaron dos enzimas nitrorreductasas específicas para catalizar la conversión de derivados de 2-nitrobenzilamina.
  • Se investigó la formación de 1H- y 2H-indazoles en función de los patrones de N-sustitución.
  • Se demostró la utilidad sintética a través de una reacción en cascada secuencial con una inmonorreductasa.

Principales resultados:

  • Se lograron excelentes conversiones (hasta >99%) de derivados de 2-nitrobenzilamina a indazoles.
  • Se sintetizaron con éxito 2H-indazoles a partir de intermedios N-sustituidos y 1H-indazoles a partir de otros derivados.
  • Se demostró una reacción en cascada escalable (escala de 50 mg) que arrojó hasta un 68% de producto aislado.

Conclusiones:

  • Se estableció un método biocatalítico novedoso y eficiente activado por nitrorreductasa para la síntesis de indazol.
  • La reacción en cascada desarrollada proporciona una ruta sostenible a los 2H-indazoles a partir de materiales de partida fácilmente disponibles.
  • Este trabajo amplía el conjunto de herramientas de transformaciones enzimáticas para acceder a compuestos heterocíclicos valiosos en el descubrimiento de fármacos.