Thermal Investigations of Annelated Triazinones—Potential Analgesic and Anticancer Agents
-
Published:2023-09-09
Issue:18
Volume:28
Page:6542
-
ISSN:1420-3049
-
Container-title:Molecules
-
language:en
-
Short-container-title:Molecules
Author:
Sztanke Małgorzata1ORCID, Sztanke Krzysztof2ORCID, Ostasz Agnieszka3ORCID, Głuchowska Halina3, Łyszczek Renata3
Affiliation:
1. Department of Medical Chemistry, Medical University of Lublin, 4A Chodźki Street, 20-093 Lublin, Poland 2. Laboratory of Bioorganic Compounds Synthesis and Analysis, Medical University of Lublin, 4A Chodźki Street, 20-093 Lublin, Poland 3. Department of General and Coordination Chemistry and Crystallography, Faculty of Chemistry, Institute of Chemical Sciences, Maria Curie-Skłodowska University, M.C. Skłodowskiej Sq. 2, 20-031 Lublin, Poland
Abstract
In this article, for the first time, TG-DSC and TG-FTIR investigations of potential pharmaceutics, i.e., analgesic and anticancer active annelated triazinones (1–9) have been presented. The thermal behaviour of these molecules was established in oxidative and inert conditions. The solid–liquid phase transition for each compound (1–9) was documented by one sharp DSC peak confirming the high purity of each sample studied. All the molecules were characterised in terms of calorimetric changes and mass changes during their heating. They revealed high thermal stability in oxidative and inert conditions. The observed tendency in thermal stability changes in relation to a substituent present at the phenyl moiety was found to be similar in air and nitrogen. It was confirmed that annelated triazinones 1–9 were stable up to a temperature range of 241–296 °C in air, and their decomposition process proceeded in two stages under oxidative conditions. In addition, it was established that their thermal stability in air decreased in the following order of R at the phenyl moiety: 4-Cl > 3,4-Cl2 > H > 3-Cl > 4-CH3 > 2-CH3 > 3-CH3 > 2-Cl > 2-OCH3. The volatile decomposition products of the investigated molecules were proposed by comparing the FTIR spectra collected during their thermogravimetric analysis in nitrogen with the spectra from the database of reference compounds. None of annelated triazinones 1–9 underwent any polymorphic transformation during thermal studies. All the compounds proved to be safe for erythrocytes. In turn, molecules 3, 6, and 9 protected red blood cells from oxidative damage, and therefore may be helpful in the prevention of free radical-mediated diseases.
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science
Reference31 articles.
1. Sztanke, K. (2008). Inventor, Medical University of Lublin, Assignee. New 8-Aryl-3-phenyl-6,7-dihydro-4H-imidazo[2,1-c][1,2,4]triazine-4-ones and Methods for Their Manufacture. (PL 199750), Polish Patent. 2. Crystal structure, antitumour and antimetastatic activities of disubstituted fused 1,2,4-triazinones;Sztanke;Bioorg. Med. Chem. Lett.,2009 3. Reversed-phase liquid chromatography with octadecylsilyl, immobilized artificial membrane and cholesterol columns in correlation studies with in silico biological descriptors of newly synthesized antiproliferative and analgesic active compounds;Janicka;J. Chromatogr. A,2013 4. Janicka, M., Sztanke, M., and Sztanke, K. (2020). Predicting the blood-brain barrier permeability of new drug-like compounds via HPLC with various stationary phases. Molecules, 25. 5. Kozak, J., Tyszczuk-Rotko, K., Sadok, I., Sztanke, K., and Sztanke, M. (2022). Application of a Screen-Printed Sensor Modified with Carbon Nanofibers for the Voltammetric Analysis of an Anticancer Disubstituted Fused Triazinone. Int. J. Mol. Sci., 23.
|
|