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.

Legnani, L., Colombo, D., Venuti, A., Pastori, C., Lopalco, L., Toma, L., et al. (2017). Diazabicyclo analogues of maraviroc: synthesis, modeling, NMR studies and antiviral activity. MEDCHEMCOMM, 8(2), 422-433 [10.1039/c6md00575f].

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

Legnani L.;
2017

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.
Articolo in rivista - Articolo scientifico
DFT;
English
422
433
12
Legnani, L., Colombo, D., Venuti, A., Pastori, C., Lopalco, L., Toma, L., et al. (2017). Diazabicyclo analogues of maraviroc: synthesis, modeling, NMR studies and antiviral activity. MEDCHEMCOMM, 8(2), 422-433 [10.1039/c6md00575f].
Legnani, L; Colombo, D; Venuti, A; Pastori, C; Lopalco, L; Toma, L; Mori, M; Grazioso, G; Villa, S
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/352051
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