Title

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

Authors

Bede, Lucie Affoue; Koffi, Alain Kouassi; Beke, Fred-Lawson Ekozias Digre; Semmeq, Abderrahmane; Badawi, Michael

Abstract

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.

Publication

Journal of Molecular Modeling, 2021, Vol 27, Issue 5, p1

ISSN

1610-2940

Publication type

Academic Journal

DOI

10.1007/s00894-021-04774-5