The role of hydrogen bonds in protein–ligand interactions. DFT calculations in 1,3-dihydrobenzimidazole-2 thione derivatives with glycinamide as model HIV RT inhibitors
✍ Scribed by Robert Kretschmer; Daniel Kinzel; Leticia González
- Publisher
- John Wiley and Sons
- Year
- 2011
- Tongue
- English
- Weight
- 993 KB
- Volume
- 112
- Category
- Article
- ISSN
- 0020-7608
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✦ Synopsis
Abstract
The structures, redshifts, binding energies, Bader analysis, and shared‐electron numbers (SENs) of 1,3‐dihydrobenzimidazole‐2‐thione (DBS) derivatives hydrogen bonded to glycinamide were calculated by the means of DFT methods. The DBS–glycinamide complex serves as a model for human immunodeficiency virus reverse transcriptase inhibitors of the N‐dimethylallyl‐6‐methyl‐4,5,6,7‐tetrahydroimidazo‐[4,5,1‐jk][1,4]‐benzodiazepin‐2(1H)‐thione family. A correlation between experimental Gibbs free energies, associated biological activities and the energy of the hydrogen bond obtained with the SEN method showed a linear relationship for different substitution patterns. Our results suggest that efficient inhibitors are those substituted in the 8‐position with electron‐withdrawing small substituents. © 2011 Wiley Periodicals, Inc. Int J Quantum Chem 112:1786–1795, 2012