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Los cannabinoides axialmente quirales: diseño, síntesis y afinidad con el receptor cannabinoide

Sara E Kearney¹, Anghelo J Gangano¹, Daniel G Barrus²

¹Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.

Journal of the American Chemical Society

|June 14, 2023

Resumen

Los investigadores desarrollaron nuevos canabinolos axialmente quirales (axCBNs) y cannabidiolos (axCBDs) mediante la modificación de la estructura cannabinoide. Estos nuevos compuestos son prometedores para mejorar las propiedades terapéuticas y el desarrollo de fármacos dirigidos al sistema endocannabinoide.

Área de la Ciencia:

Química medicinal
Síntesis orgánica
Farmacología

Sus antecedentes:

El andamio resorcinol-terpeno es clave para desarrollar terapias dirigidas al sistema endocannabinoide.
Los canabinolos axialmente quirales (axCBN) son análogos no naturales con propiedades físicas y biológicas mejoradas.
Los cannabidiolos axialmente quirales (axCBD) son una nueva clase inspirada en el cannabidiol (CBD).

Objetivo del estudio:

Explorar la filosofía de diseño y las estrategias sintéticas para los cannabinoides axialmente quirales (axCBN y axCBD).
Para analizar el atropisomerismo de los axCannabinoides.
Evaluar la afinidad y la actividad funcional de axCannabinoids en los receptores cannabinoides.

Principales métodos:

Diseño y síntesis de los canabinolos axialmente quirales (axCBN) y los cannabidiolos (axCBD).
Análisis del atropisomerismo en los cannabinoides ax.
Evaluación de la afinidad de unión al receptor y la actividad funcional en los receptores cannabinoides.

Principales resultados:

Síntesis exitosa de nuevos axCBNs y axCBDs.
Caracterización del atropisomerismo axCannabinoide (clase 1 y 3).
Se ha demostrado la retención y, en algunos casos, el fortalecimiento de la afinidad y la actividad en los receptores cannabinoides.

Conclusiones:

Los cannabinoides axialmente quirales representan una nueva dirección prometedora para el diseño de nuevos ligandos cannabinoides.
Estos compuestos ofrecen potencial para el descubrimiento de fármacos y la exploración del sistema endocannabinoide.
Las modificaciones estructurales únicas mejoran las propiedades del ligando para aplicaciones terapéuticas.

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