Wydział Chemii

Iwona Bryndal

Marcin Stolarczyk

Aleksandra Mikołajczyk

Magdalena Krupińska

Anna Pyra

Marcin Mączyński

Agnieszka Matera-Witkiewicz

2024

International Journal of Molecular Sciences

25

2076/1-2076/27

10.3390/ijms25042076

Naukowa

Angielski

Artykuł

Recently, 5-[(4-ethoxyphenyl)imino]methyl-N-(4-fluorophenyl)-6-methyl-2-phenylpyrimidin-4-amine has been synthesized, characterized, and evaluated for its antibacterial activity against Enterococcus faecalis in combination with antineoplastic activity against gastric adenocarcinoma. In this study, new 5-iminomethylpyrimidine compounds were synthesized which differ in the substituent(s) of the aromatic ring attached to the imine group. The structures of newly obtained pyrimidine Schiff bases were established by spectroscopy techniques (ESI-MS, FTIR and ¹H NMR). To extend the current knowledge about the features responsible for the biological activity of the new 5-iminomethylpyrimidine derivatives, low-temperature single-crystal X-ray analyses were carried out. For all studied crystals, intramolecular N–H∙∙∙N hydrogen bonds and intermolecular C–H∙∙∙F interactions were observed and seemed to play an essential role in the formation of the structures. Simultaneously, their biological properties based on their cytotoxic features were compared with the activities of the Schiff base (III) published previously. Moreover, computational investigations, such as ADME prediction analysis and molecular docking, were also performed on the most active new Schiff base (compound 4b). These results were compared with the highest active compound III.

anticancer activity, cytotoxic activity, pyrimidine Schiff bases, X-ray structures, ADME prediction analysis

CC-BY

https://dx.doi.org/10.3390/ijms25042076

http://www.mdpi.com/journal/metals