Theoretical study on the origins of sildenafil tautomers’ relative stability
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Dariusz Pajka
Abstract
Tautomers of sildenafil (5-{2-Ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one), a drug commonly used for treating the erectile dysfunction and pulmonary arterial hypertension were studied computationally at the DFT (B3LYP/6-311++G**) level. Four possible structures of sildenafil tautomers structures were considered. The geometries and chemical shifts of carbon and nitrogen nuclei were calculated and compared with available experimental data. The theoretical calculations proved to be consistent with experimental data and indicate the same lowest energy sildenafil structure. The energies of the all considered sildenafil tautomers were determined and ranked according to their energy values. This article presents calculations of several properties (aromaticity, atomic charges, atomic energies, intramolecular hydrogen bonding) and discusses their influence on the relative energies of sildenafil tautomers.
Acknowledgments
This research was carried out with the support of the Interdisciplinary Centre for Mathematical and Computational Modelling at the University of Warsaw (ICM UW).
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Author contribution: This paper in a journal version of the BSc work of Dariusz Pajka entitled “Równowagi tautomeryczne sildenafilu” (in Polish). Dariusz Pajka performed calculations and elaborated data under supervision of Krzysztof K. Zborowski. Both authors interpreted data and prepared the draft of the manuscript. Urszula Lelek-Borkowska helped in preparation of the final manuscript version.
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Research funding: None declared.
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Conflict of interest statement: No potential conflict of interest was reported by the authors.
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© 2022 Walter de Gruyter GmbH, Berlin/Boston
Artikel in diesem Heft
- Frontmatter
- Original Papers
- Suppression of steel corrosion via some gemini cationic surfactant-based Schiff base: experimental and theoretical investigations
- Synthesis of poly (N-isopropyl acrylamide-co-2-acrylamido methylpropane sulfonic acid) hydrogel containing copper and nickel nanoparticles with easy recycling and efficient catalytic potential
- Eco-benign preparation of biosorbent using Momordica Charantia for the efficient removal of Cr(VI) ions from wastewater
- Oil mediated green synthesis of nano silver in the presence of surfactants for catalytic and food preservation application
- Adsorption properties of metal functionalized fullerene (C59Au, C59Hf, C59Ag, and C59Ir) nanoclusters for application as a biosensor for hydroxyurea (HXU): insight from theoretical computation
- Evaluation of diethylenetriaminepentaacetic acid modified chitosan immobilized in amino-carbmated alginate matrix as a low cost adsorbent for effective Cu(II) recovery
- Screening of four accelerated synthesized techniques in green fabrication of ZnO nanoparticles using Willow leaf extract
- Preparation and comparative evaluation of PVC/PbO and PVC/PbO/graphite based conductive nanocomposites
- Optical and topographic characteristics of silver films deposited from a colloidal solution on polyelectrolytes for IgG-FITC fluorescence analysis
- The three pyridazines, three naphthyridines and two azoles: effect of the position of the second heteroatom on pKaH of their eight conjugate acids
- Theoretical study on the origins of sildenafil tautomers’ relative stability
- Application of the Lennard-Jones potential for calculating the surface tension and the formation enthalpy of a binary solution
- Ultrasonic supported dye removal by a novel biomass
- A novel synthesis of graphene oxide-titanium dioxide (GO-TiO2) and graphene oxide-zinc oxide (GO-ZnO) nanocomposites and their application as effective, reusable photocatalysts for degradation of methylene blue (MB) dye
- Review Article
- Photocatalytic hydrogen generation using TiO2: a state-of-the-art review
Artikel in diesem Heft
- Frontmatter
- Original Papers
- Suppression of steel corrosion via some gemini cationic surfactant-based Schiff base: experimental and theoretical investigations
- Synthesis of poly (N-isopropyl acrylamide-co-2-acrylamido methylpropane sulfonic acid) hydrogel containing copper and nickel nanoparticles with easy recycling and efficient catalytic potential
- Eco-benign preparation of biosorbent using Momordica Charantia for the efficient removal of Cr(VI) ions from wastewater
- Oil mediated green synthesis of nano silver in the presence of surfactants for catalytic and food preservation application
- Adsorption properties of metal functionalized fullerene (C59Au, C59Hf, C59Ag, and C59Ir) nanoclusters for application as a biosensor for hydroxyurea (HXU): insight from theoretical computation
- Evaluation of diethylenetriaminepentaacetic acid modified chitosan immobilized in amino-carbmated alginate matrix as a low cost adsorbent for effective Cu(II) recovery
- Screening of four accelerated synthesized techniques in green fabrication of ZnO nanoparticles using Willow leaf extract
- Preparation and comparative evaluation of PVC/PbO and PVC/PbO/graphite based conductive nanocomposites
- Optical and topographic characteristics of silver films deposited from a colloidal solution on polyelectrolytes for IgG-FITC fluorescence analysis
- The three pyridazines, three naphthyridines and two azoles: effect of the position of the second heteroatom on pKaH of their eight conjugate acids
- Theoretical study on the origins of sildenafil tautomers’ relative stability
- Application of the Lennard-Jones potential for calculating the surface tension and the formation enthalpy of a binary solution
- Ultrasonic supported dye removal by a novel biomass
- A novel synthesis of graphene oxide-titanium dioxide (GO-TiO2) and graphene oxide-zinc oxide (GO-ZnO) nanocomposites and their application as effective, reusable photocatalysts for degradation of methylene blue (MB) dye
- Review Article
- Photocatalytic hydrogen generation using TiO2: a state-of-the-art review
