Funct. Mater. 2022; 29 (4): 611-620.
Stress testing of 2,5-dihydro-1H-pyrrol-3-yl substituted acetic acid
1Division of Functional Materials Chemistry, State Scientific Institution "Institute for Single Crystals", National Academy of Sciences of Ukraine, 60 Nauky Ave., 61072 Kharkiv, Ukraine
2Chemistry Faculty, V.N.Karazin Kharkiv National University, 4 Svobody Sq., 61022 Kharkiv, Ukraine
Stress testing was performed on 2-(2-(4-bromophenyl)-4-hydroxy-1-(5-methylisoxazol-3-yl)-5-oxo-2,5-dihydro-1H-pyrrol-3-yl) acetic acid, Bropa, to determine the weaknesses of pyrrolone-type heterocycles to various stressors, establish the degradation pathways and found the possible approaches to overcome potential stability problems. Since other pyrrolone derivatives had previously shown high activity against influenza A/H1N1 virus and low cytotoxicity, this class was considered a promising source of the new active substances. The influence of temperature, alkaline and acidic media, daylight, UV irradiation and hydrogen peroxide on the stability of Bropa was studied. Several analytical procedures using HPLC, FTIR, and UV-vis spectroscopy were developed for the qualitative and quantitative analysis of Bropa and the impurities in the test solutions. Bropa was found to be resistant to daylight, temperature, alkaline and acidic media, with impurity levels increasing by only 0.3-0.7 %. However, the compound proved unstable in UV tests and tests with hydrogen peroxide (30 % and 3 %), as the content of the Bropa decreased to 11.7 %, 8.3 %, and 41.2 %, respectively, with many new impurities formed, showing the susceptibility of the 5-oxo-2,5-dihydro-1H-pyrrol-3-yl fragment to oxidation and photoinduced chemical reactions. The results indicated that the photochemical and oxidative stability properties of pyrrolone-type heterocycles need to be improved to significantly reduce the number of degradation products.
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