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Investigation of tautomerism of 1,3,5-triazine derivative, stability, and acidity of its tautomers from density functional theory.

Lucie Affoue BedeAlain Kouassi KoffiFred-Lawson Ekozias Digre BekeAbderrahmane SemmeqMichaël Badawi
Published in: Journal of molecular modeling (2021)
Recent studies have identified N2,N4-bis(4-fluorophenethyl)-N6-(3-(dimethylamino)propyl)-1,3,5-triazine-2,4,6-triamine (1TZ(7,8,9)) as a potent, pure antagonist that inhibits thermosensory transient receptor potential vanilloid 1 channel (TRPV1) channel activity. This study provides theoretical data on the stability and acidity of the tautomers of this molecule. We show that this triazine can exist as three predominant tautomers (2TZ(5,7,8), 4TZ(3,7,9), 7TZ(1,8,9)). In the aqueous phase, equilibrium constants calculations show that only the tautomeric equilibria between 1TZ(7,8,9) and the three most stable triazines can be present which suggests that these three tautomeric equilibria would be the basis of 1TZ(7,8,9)'s biological activity.
Keyphrases
  • density functional theory
  • molecular dynamics
  • ionic liquid
  • molecular dynamics simulations
  • electronic health record
  • risk assessment
  • big data
  • deep learning
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  • high resolution
  • cerebral ischemia