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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

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