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Acceso escalable a las arilomicinas a través de la lógica de funcionalización C-H
David S Peters1, Floyd E Romesberg1, Phil S Baran1
1Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Journal of the American Chemical Society
|January 31, 2018
Resumen
Los investigadores desarrollaron una nueva síntesis simplificada para los antibióticos de arilomicina. Este método utiliza el acoplamiento de fenol oxidativo mediado por cobre para una macrociclado eficiente, lo que permite un acceso más fácil a estos agentes antibacterianos prometedores.
Área de la Ciencia:
- Química medicinal
- Síntesis orgánica
- Productos naturales
Sus antecedentes:
- Las arilomicinas son potentes productos naturales antibacterianos en desarrollo preclínico.
- Las rutas de síntesis existentes son complejas, costosas y requieren mucho tiempo para escalar.
- El acceso simplificado a los análogos de la arilomicina es crucial para la investigación futura.
Objetivo del estudio:
- Desarrollar una ruta sintética simplificada para los análogos de la arilomicina.
- Para permitir la producción escalable de estos agentes antibacterianos prometedores.
- Sintetizar y evaluar nuevos análogos de la arilomicina.
Principales métodos:
- Acoplamiento de fenol oxidativo mediado por cobre para la macrociclización.
- Logía de funcionalización C-H para una síntesis simplificada.
- Síntesis a escala de gramos y síntesis total formal de las arilomicinas.
Principales resultados:
- Se estableció una ruta sintética novedosa, operacionalmente simple y escalable.
- Se logró la mayor macrociclización de su tipo.
- Se sintetizó y evaluó biológicamente una colección de nuevos análogos de la arilomicina.
Conclusiones:
- La nueva estrategia sintética simplifica significativamente la producción de análogos de arilomicina.
- Este enfoque facilita el desarrollo de nuevos agentes antibacterianos.
- El método es susceptible de síntesis a gran escala para el desarrollo preclínico.
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