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<p>Guanoxabenz is one of the <i>α</i>2 adrenergic receptor agonist, with a Ki of 4000&#xa0;nM and the fully activated form 40&#xa0;nM for the <i>α</i>2 adrenoceptor. Guanoxabenz is a metabolite of guanabenz. Guanoxabenz (1-(2,6-dichlorobenzylidene-amino)-3-hydroxyguanidinea) and guanabenz (1- (2,6 dichlorobenzylidene-amino)-3-guanidine) are both known as centrally active antihypertensive drugs. In this study, the Guanoxabenz’s tautomers stabilities, geometries data, HOMO &amp; LUMO orbitals (shapes and energy levels), <i>ΔΕ</i><sub><i>HOMO-LUMO</i></sub> gaps, Mulliken charges, dipole moments, the thermodynamic and kinetic stabilities in H<sub>2</sub>O media as an important biological solvent and the selected media (vacuum, Et-OH, DMSO and CH<sub>2</sub>Cl<sub>2</sub>) were studied for the tautomers of Guanoxabenz. Also, the equilibrium constant was applied to investigate the interconversion equilibrium between the different tautomers of Guanoxabenz (GO1, GO2, GO3cis and GO3trans) in the discussed media. We have also investigated the modeling of the oxidation of guanobenz to guanoxabenz in the presence of CYP 450 by DFT-B3LYP/6-31G* method. The two pathways for guanabenz oxidation (N-oxidation and H-abstraction) were also modeled in this study.</p>

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N-oxidation and H-abstraction mechanism of Guanabenz and solvent effects, structural and conformational properties of Guanabenzoxide tautomers; A first principle DFT study

  • 期刊论文

  • 发表日期：

    2025年10月21日

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  • Binazir Fatemimanesh,
  • Avat Arman Taherpour

摘要

Guanoxabenz is one of the α2 adrenergic receptor agonist, with a Ki of 4000 nM and the fully activated form 40 nM for the α2 adrenoceptor. Guanoxabenz is a metabolite of guanabenz. Guanoxabenz (1-(2,6-dichlorobenzylidene-amino)-3-hydroxyguanidinea) and guanabenz (1- (2,6 dichlorobenzylidene-amino)-3-guanidine) are both known as centrally active antihypertensive drugs. In this study, the Guanoxabenz’s tautomers stabilities, geometries data, HOMO & LUMO orbitals (shapes and energy levels), ΔΕHOMO-LUMO gaps, Mulliken charges, dipole moments, the thermodynamic and kinetic stabilities in H2O media as an important biological solvent and the selected media (vacuum, Et-OH, DMSO and CH2Cl2) were studied for the tautomers of Guanoxabenz. Also, the equilibrium constant was applied to investigate the interconversion equilibrium between the different tautomers of Guanoxabenz (GO1, GO2, GO3cis and GO3trans) in the discussed media. We have also investigated the modeling of the oxidation of guanobenz to guanoxabenz in the presence of CYP 450 by DFT-B3LYP/6-31G* method. The two pathways for guanabenz oxidation (N-oxidation and H-abstraction) were also modeled in this study.