Novel functionalized thiazoles were prepared by the Hantzsch reaction from 3-[(4hydroxyphenyl)carbamothioylamino]-2-methylpropanoic acid and the corresponding α-halocarbonyl compounds in good yields. A series of chemical transformations of the obtained products were carried out, and new functionalized thiazole derivatives with aliphatic, aromatic and heterocyclic substituents were synthesized. 4-Phenyl-substituted N-(4-hydroxyphenyl)-N-carboxyalkylaminothiazoles were used as precursors for the synthesis of bis(thiazol-5-yl)methane derivatives, which then were screened for their antibacterial, antioxidant activities.
Non-small cell lung cancer (NSCLC) remains a leading cause of cancer-associated mortalities worldwide. Therefore, it is crucial to develop a novel therapeutic option targeting localized and metastatic NSCLC. In this paper, we describe the synthesis and biological activity characterization of naphthoquinone derivatives bearing selective anticancer activity to NSCLC via a COX-2 mediated pathway. The biological evaluation of compounds 9–16 showed promising structure-dependent anticancer activity on A549 cells in 2D and 3D models. Compounds were able to significantly (p < 0.05) reduce the A549 viability after 24 h of treatment in comparison to treated control. Compounds 9 and 16 bearing phenylamino and 4-hydroxyphenylamino substituents demonstrated the most promising anticancer activity and were able to induce mitochondrial damage and ROS formation. Furthermore, most promising compounds showed significantly lower cytotoxicity to non-cancerous Vero cells. The in silico ADMET properties revealed promising drug-like properties of compounds 9 and 16. Both compounds demonstrated favorable predicted GI absorption values, while only 16 was predicted to be permeable through the blood–brain barrier. Molecular modeling studies identified that compound 16 is able to interact with COX-2 in arachidonic acid site. Further studies are needed to better understand the safety and in vivo efficacy of compounds 9 and 16.
A series of novel 1,2‐bissubstituted disulfanes bearing beta‐amino acid, dihydropyrimidine‐2,4‐(1H,3H)‐dione, hydrazide, hydrazone and azole moieties were synthesized. The antibacterial activity was evaluated by determining minimum inhibition (by broth microdilution) and minimum bactericidal (by growth on agar) concentrations. The assessment revealed that MIC values for L. monocytogenes varied between 3.9 and 62.5 μg/mL as well as for S. aureus ranged between 7.8 and 250 μg/mL, with the exception of one compound with much weaker MIC of 500 μg/mL. The MBC values for L. monocytogenes have been found to be of 7.8–250 μg/mL, while S. aureus demonstrated the higher resistance and MBCs varied in the range of 7.8–500 μg/mL. The determined MBC/MIC ratios showed that eleven compounds were classified bactericidal agents for all tested bacteria.
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