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An Exhaustive Conformational Evaluation of the HIV‐1 Inhibitor BMS‐378806 through Theoretical Calculations and Nuclear Magnetic Resonance Spectroscopy
Author(s) -
Colombo Diego,
Villa Stefania,
Solano Lucrezia,
Legnani Laura,
Mari Albini Franca,
Toma Lucio
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900178
Subject(s) - chemistry , nuclear magnetic resonance spectroscopy , envelope (radar) , derivative (finance) , spectroscopy , human immunodeficiency virus (hiv) , stereochemistry , nuclear magnetic resonance , computational chemistry , crystallography , physics , medicine , telecommunications , radar , family medicine , quantum mechanics , computer science , financial economics , economics
BMS‐378806 ( 1 ) is an azaindole derivative known to interfere with the HIV‐1 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 1 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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)