Journal
MOLECULES
Volume 28, Issue 4, Pages -Publisher
MDPI
DOI: 10.3390/molecules28041735
Keywords
annelated triazinylacetic acid ethyl esters; anticancer agents; thermal stability; thermal behaviour; thermal degradation course; TG-DSC; TG-FTIR
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To study the thermal behavior and decomposition pathway of a class of potential molecular pharmaceutics, thermal studies were conducted under inert and oxidative atmospheres. It was found that the decomposition pathways of the compounds were different in the two atmospheres, with higher thermal stability observed under a synthetic air atmosphere. The oxidative decomposition process of the studied molecules was found to occur in three stages accompanied by exothermic effects. The compounds exhibited polymorphic behavior, with the meta-chloro derivative showing the most interesting results.
To avoid problems associated with the storage and processing of newly developed potential medicines, there is a need to carry out thermal studies in the preclinical phase of drug development. The thermal behaviour and decomposition pathway of a whole novel class of patented potential molecular pharmaceutics, i.e., ethyl 2-[4-oxo-8-(R-phenyl)-4,6,7,8-tetrahydroimidazo[2,1-c][1,2,4]triazin-3-yl]acetates (1-6) were reported for the first time in inert and oxidative atmospheres. The experiments were conducted with the use of simultaneous thermogravimetry/differential scanning calorimetry (TG-DSC) and simultaneous thermogravimetry coupled with Fourier transform infrared spectroscopy (TG-FTIR). The decomposition pathways of compounds 1-6 were found to be different under oxidative and inert conditions. It was proven that the investigated molecules reveal higher thermal stability under a synthetic air atmosphere than under a nitrogen atmosphere, and their decomposition is preceded by the melting process. Among all the investigated compounds, only the meta-chloro derivative (4) was found to exhibit interesting polymorphic behaviour at a low heating rate (10 degrees C min(-1)). It was proven that the oxidative decomposition process of the studied molecules proceeds in three overlapping stages accompanied by strong exothermic effects. Additionally, it was concluded that the title compounds were stable up to a temperature of 195-216 degrees C in an atmosphere of synthetic air, and their thermal stability decreased in the order of R at the benzene ring: 4-CH3 > 3,4-Cl-2 > 4-Cl > H > 2-OCH3 > 3-Cl.
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