Synthesis of a des-B-ring bryostatin analogue leads to an unexpected ring expansion of the bryolactone core.
J Am Chem Soc
; 136(38): 13202-8, 2014 Sep 24.
Article
en En
| MEDLINE
| ID: mdl-25207434
ABSTRACT
A convergent synthesis of a des-B-ring bryostatin analogue is described. This analogue was found to undergo an unexpected ring expansion of the bryolactone core to generate the corresponding 21-membered macrocycle. The parent analogue and the ring-expanded product both displayed nanomolar binding affinity for PKC. Despite containing A-ring substitution identical to that of bryostatin 1 and displaying bryostatin-like biological function, the des-B-ring analogues displayed a phorbol-like biological function in cells. These studies shed new light on the role of the bryostatin B-ring in conferring bryo-like biological function to bryostatin analogues.
Texto completo:
1
Banco de datos:
MEDLINE
Asunto principal:
Productos Biológicos
/
Briozoos
/
Brioestatinas
/
Antineoplásicos
Límite:
Animals
/
Humans
Idioma:
En
Revista:
J Am Chem Soc
Año:
2014
Tipo del documento:
Article
País de afiliación:
Estados Unidos