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,

Colombo, D., Villa, S., Solano, L., Legnani, L., Marinone, F., Toma, L. (2009). An exhaustive conformational evaluation of the HIV-1 inhibitor BMS-378806 through theoretical calculations and nuclear magnetic resonance spectroscopy. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009(19), 3178-3183 [10.1002/ejoc.200900178].

An exhaustive conformational evaluation of the HIV-1 inhibitor BMS-378806 through theoretical calculations and nuclear magnetic resonance spectroscopy

LEGNANI, LAURA;
2009

Abstract

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,
Articolo in rivista - Articolo scientifico
Antiviral agents; Density functional calculations; Molecular modeling; Nitrogen heterocycles; NMR spectroscopy;
English
3178
3183
6
Colombo, D., Villa, S., Solano, L., Legnani, L., Marinone, F., Toma, L. (2009). An exhaustive conformational evaluation of the HIV-1 inhibitor BMS-378806 through theoretical calculations and nuclear magnetic resonance spectroscopy. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009(19), 3178-3183 [10.1002/ejoc.200900178].
Colombo, D; Villa, S; Solano, L; Legnani, L; Marinone, F; Toma, L
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/351954
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