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Diversificación desconstructiva de las aminas cíclicas

Jose B Roque¹, Yusuke Kuroda¹, Lucas T Göttemann¹

¹Department of Chemistry, University of California, Berkeley, CA, USA.

|November 2, 2018

Resumen

Este estudio introduce un nuevo método de funcionalización deconstructiva para los heterociclos de nitrógeno saturado. Permite la remodelación esquelética de aminas cíclicas en haloaminas acíclicas versátiles, útiles para el descubrimiento de fármacos.

Área de la Ciencia:

Química orgánica
Química sintética
Química medicinal

Sus antecedentes:

La funcionalización deconstructiva generalmente implica la escisión de los enlaces dobles carbono-carbono.
Los métodos para la escisión y la funcionalización de enlaces únicos carbono-carbono, especialmente en sistemas cíclicos, son limitados.
Los heterociclos de nitrógeno son andamios cruciales en muchas moléculas bioactivas.

Objetivo del estudio:

Desarrollar una estrategia de deconstrucción para los heterociclos de nitrógeno saturado.
Para lograr la escisión y la funcionalidad de enlace único C(sp3) -N y C(sp3) -C(sp3).
Para generar versátiles derivados de aminas acíclicas que contienen halógenos.

Principales métodos:

Secuencia de clivado de enlace único de los heterociclos de nitrógeno C ((sp3) -N y C ((sp3) -C ((sp3)).
Funcionalización a través de la formación de enlaces halógenos C ((sp3).
Aplicación a la diversificación en fase avanzada de los péptidos que contienen prolina.

Principales resultados:

Transformación exitosa de las piperidinas y pirrolidinas en haloaminas acíclicas.
Demostración de la remodelación esquelética de las aminas cíclicas (salto de andamio).
Generación de productos intermedios versátiles para otras modificaciones sintéticas.

Conclusiones:

El método desarrollado proporciona una nueva vía para la funcionalización de los heterociclos de nitrógeno saturado.
Las haloaminas acíclicas sirven como bloques de construcción valiosos para diversas estructuras moleculares.
Esta estrategia facilita la diversificación en las últimas etapas del descubrimiento y desarrollo de fármacos.

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