Photorearrangement of Quinoline-Protected Dialkylanilines and the Photorelease of Aniline-Containing Biological Effectors.
J Org Chem
; 84(11): 7342-7353, 2019 06 07.
Article
em En
| MEDLINE
| ID: mdl-31095378
ABSTRACT
The direct release of dialkylanilines was achieved by controlling the outcome of a photorearrangement reaction promoted by the (8-cyano-7-hydroxyquinolin-2-yl)methyl (CyHQ) photoremovable protecting group. The substrate scope was investigated to obtain structure-activity relationships and to propose a reaction mechanism. Introducing a methyl substituent at the 2-methyl position of the CyHQ core enabled the bypass of the photorearrangement and significantly improved the aniline release efficiency. We successfully applied the strategy to the photoactivation of mifepristone (RU-486), an antiprogestin drug that is also used to induce the LexPR gene expression system in zebrafish and the gene-switch regulatory system based on the pGL-VP chimeric regulator in mammals.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Quinolinas
/
Compostos de Anilina
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2019
Tipo de documento:
Article
País de afiliação:
Emirados Árabes Unidos