Drug-like properties and complete physicochemical profile of pyrazine‑2‑amidoxime: a combined multi-experimental and computational studies

Agnieszka Chylewska , Małgorzata Biedulska , Angelika Głębocka , Ewa D. Raczyńska , Mariusz Makowski


Pyrazine 2 amidoxime (PAOX) is a prototypical sp2-hybridized amidoxime. Although, we described first time in details PAOX structure in solid state, the profile of PAOX behavior in aqueous solution still needs to be improved. While, acid-base properties of PAOX have been tried to define just once, the presented description was not complete and based only on the results of potentiometry during complexometric studies. The selection of method gives rise problems to observation the protonation or deprotonation processes of compound studied. Due to above, the presented studies show first time the complete description of PAOX acid-base properties by obtaining its pKa, solubility, partition (P) and distribution (D) coefficients using various methods. Among them, experiments: potentiometry; UV spectrophotometry by using Hammett's function and pH-metric titrations; cyclic voltammetry (CV) with glassy carbon electrode (GCE) and with GCE electropolymerized by poly L glycine (PGGCE); 1H NMR and theoretical calculations (DFT). Generally, combined four types of experimental and theoretical methods were used to estimate PAOX macro acidic-dissociation constants values. Moreover, log P and log D were determined spectrophotometrically and calculated also by DFT methods. No previous reports were found in the presented form regarding the complete drug-like properties, including negative together with positive values of pKa. Additionally, we proved by our electrochemical results that the quantitative analysis of PAOX do not need the special conditions of the electrode used in research. Hence, the comparison of our results to those described in the literature about analysis made for others, amidoxime derivatives.
Author Agnieszka Chylewska (FCh/KChBionieorg./LII)
Agnieszka Chylewska,,
- Laboratory of Intermolecular Interactions
, Małgorzata Biedulska (FCh/KChBionieorg./LII)
Małgorzata Biedulska,,
- Laboratory of Intermolecular Interactions
, Angelika Głębocka (FCh/KChBionieorg./LII)
Angelika Głębocka,,
- Laboratory of Intermolecular Interactions
, Ewa D. Raczyńska - [Szkoła Główna Gospodarstwa Wiejskiego]
Ewa D. Raczyńska,,
, Mariusz Makowski (FCh/KChBionieorg./LII)
Mariusz Makowski,,
- Laboratory of Intermolecular Interactions
Journal seriesJournal of Molecular Liquids, ISSN 0167-7322, (N/A 100 pkt)
Issue year2019
Publication size in sheets0.85
Keywords in EnglishPyrazine 2 amidoxime, macro- and micro-pKa, Log P(D) and solubility, potentiometry, spectroscopies and electrochemistry, Hammett acidity function, DFT calculations
ASJC Classification1606 Physical and Theoretical Chemistry; 1607 Spectroscopy; 2504 Electronic, Optical and Magnetic Materials; 2505 Materials Chemistry; 3104 Condensed Matter Physics; 3107 Atomic and Molecular Physics, and Optics
URL https://doi.org/10.1016/j.molliq.2018.11.147
Languageen angielski
Score (nominal)100
Score sourcejournalList
ScoreMinisterial score = 100.0, 03-07-2020, ArticleFromJournal
Publication indicators WoS Citations = 0.000; Scopus Citations = 4.000; Scopus SNIP (Source Normalised Impact per Paper): 2018 = 1.275; WoS Impact Factor: 2018 = 4.561 (2) - 2018=4.136 (5)
Citation count*4 (2020-07-03)
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* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.
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