Document Report Card

ID: ALA4138064

Journal: Medchemcomm

Title: Diazabicyclo analogues of maraviroc: synthesis, modeling, NMR studies and antiviral activity.

Authors: Legnani L, Colombo D, Venuti A, Pastori C, Lopalco L, Toma L, Mori M, Grazioso G, Villa S.

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.

CiteXplore: 30108760

DOI: 10.1039/C6MD00575F