Diazabicyclo analogues of maraviroc: synthesis, modeling, NMR studies and antiviral activity.
Medchemcomm
; 8(2): 422-433, 2017 Feb 01.
Article
em En
| MEDLINE
| ID: mdl-30108760
ABSTRACT
Two diazabicyclo analogues of maraviroc, in which the azabicyclooctane moiety is replaced by diazabicyclooctane or diazabicyclononane, were synthesized and tested, through a viral neutralization assay, on a panel of six pseudoviruses. The diazabicyclooctane derivative maintained a significant infectivity reduction power, whereas the diazabicyclononane was less effective. Biological data were rationalized through a computational study that allowed the conformational preferences of the compounds to be determined and a correlation between the inhibitory activity, the bridge length of the bicycle, and the rotational barrier around dihedral angle τ7 to be hypothesized. A high-field NMR analysis supported the modeling results.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Medchemcomm
Ano de publicação:
2017
Tipo de documento:
Article
País de afiliação:
Itália