TY - JOUR
T1 - An exhaustive conformational evaluation of the HIV-I inhibitor BMS-378806 through theoretical calculations and nuclear magnetic resonance spectroscopy
AU - Colombo, Diego
AU - Villa, Stefania
AU - Solano, Lucrezia
AU - Legnani, Laura
AU - Albini, Franca Marinone
AU - Toma, Lucio
PY - 2009/7
Y1 - 2009/7
N2 - BMS-378806 (1) is an azaindole derivative known to interfere with the HIV-I entry process by targeting the viral gp120 envelope glycoprotein and inhibiting its interaction to cellular CD4 receptors. To give a detailed comprehension of its conformational features, a theoretical study of 1 was performed at the B3LYP/6-31G(d) level of calculation. Tenths of populated conformations were located and grouped, into four families corresponding to the possible arrangements at the two planar amido functions. In agreement with these results, the high-field H NMR spectrum, of 1, recorded at 248 K, showed four distinct series of signals easily attributable to each family, thus confirming on experimental grounds the very high degree of conformational mobility of the compound,
AB - BMS-378806 (1) is an azaindole derivative known to interfere with the HIV-I entry process by targeting the viral gp120 envelope glycoprotein and inhibiting its interaction to cellular CD4 receptors. To give a detailed comprehension of its conformational features, a theoretical study of 1 was performed at the B3LYP/6-31G(d) level of calculation. Tenths of populated conformations were located and grouped, into four families corresponding to the possible arrangements at the two planar amido functions. In agreement with these results, the high-field H NMR spectrum, of 1, recorded at 248 K, showed four distinct series of signals easily attributable to each family, thus confirming on experimental grounds the very high degree of conformational mobility of the compound,
KW - Antiviral agents
KW - Density functional calculations
KW - Molecular modeling
KW - Nitrogen heterocycles
KW - NMR spectroscopy
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U2 - 10.1002/ejoc.200900178
DO - 10.1002/ejoc.200900178
M3 - Article
AN - SCOPUS:67650872918
SP - 3178
EP - 3183
JO - Justus Liebigs Annalen der Chemie
JF - Justus Liebigs Annalen der Chemie
SN - 0075-4617
IS - 19
ER -