Сибирский федеральный университет

Тип публикации: статья из журнала

Год издания: 2024

Идентификатор DOI: 10.1515/zpch-2023-0436

Ключевые слова: 1-Phenylpiperazine, fumaric acid, single-crystal X-ray diffraction, Hirshfeld surfaces, quantum chemical calculations, molecular docking

Аннотация: <jats:title>Abstract</jats:title> <jats:p>The complexation between fumaric acid (FA) and 1-phenylpiperazine (1 PP) is a fruitful cooperation that allowed the preparation of a new organic crystal entitled (4-phenylpiperazin-1-ium) hydrogenfumarate denoted by 4PPHFUM, which is reported in the present manuscript. This new substance is created by the slow evaporation that occurs when 1-phenylpiperazine and fumaric acid are combined in a stoichiometric 1:1 ratio. The stacking of the crystal is provided by O–H⋯O, N–H⋯O and C–H⋯O hydrogen bonds, also supported by C–H⋯π interactions between the organic cations. The importance of these interactions in the formation of this new crystal is confirmed by the Hirshfeld surface analysis which showed that H-bonds and supramolecular C–H⋯π interactions account for about half of the non-covalent interactions existing in this compound. These non-covalent bonds that encompass the synthesis and design of this supramolecule have also been analyzed in detail using a quantum chemical computational study. Using the docking – based drug design strategy, we investigated the therapeutic effect of this cooperative outcome between fumaric acid and 1-phenylpiperazine to demonstrate the improved therapeutic property of this novel non-covalent compound as a tyrosinase inhibitor. 4PPHFUM was found to be a potent tyrosinase inhibitor with high interaction energy with its protein, higher than that of the most potent tyrosinase inhibitors (thiamidol, hydroquinone, resorcinol, hexylresorcinol and kojic acid).</jats:p>

Журнал: Zeitschrift fur Physikalische Chemie

Выпуск журнала: Т.238, №3

Номера страниц: 509-529

ISSN журнала: 09429352

Место издания: Munich

Издатель: Oldenbourg Wissenschaftsverlag GmbH

• Jemai Mahdi (Laboratory of Material Chemistry, Faculty of Sciences of Bizerte, University of Carthage)
• Issaoui Noureddine (Quantum Physics Laboratory, Faculty of Sciences, University of Monastir)
• Roisnel Thierry (Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes))
• Kazachenko Aleksandr S. (Siberian Federal University)
• Marouani Houda (Laboratory of Material Chemistry, Faculty of Sciences of Bizerte, University of Carthage)
• Al-Dossary Omar M. (Department of Physics and Astronomy, College of Science, King Saud University)

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