Synthesis, cytotoxicity and antioxidant activity of new 1,3-dimethyl-8-(chromon-3-yl)-xanthine derivatives containing 2,6-di-tert-butylphenol fragments
| Autor: | Elizaveta K. Melnikova, Gleb S. Denisov, Stanislav S. Shatokhin, Alina A. Markova, Boris M. Bulychev, S.C. Gagieva, Vladislav A. Tuskaev, Eduard T. Oganesyan, Dmitry I. Pozdnyakov |
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| Rok vydání: | 2022 |
| Předmět: | |
| Zdroj: | New Journal of Chemistry. 46:621-631 |
| ISSN: | 1369-9261 1144-0546 |
| Popis: | The condensation of 3-formylchromones and 6-amino-5-((3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)amino)-1,3-dimethyl-pyrimidine-2,4(1H,3H)-dione allowed us to synthesize chromone based hybrids containing additional pharmacophores - xanthine and sterically hindered phenol fragments. Novel compounds have been characterized by 1H and 13C NMR spectroscopy, mass spectrometry and elemental analysis. The molecular structure of compound 2 was determined by single crystal X-ray diffraction studies. Compounds 2-9, 11, 12 exhibit cytotoxic activity against human colon carcinoma cells HCT116 and breast carcinoma cells MCF7 at submicromolar concentrations. Compound 11 containing 6,8-dimethylchromone core has the highest cytotoxicity against tumor cells and lowest at non-tumor fibroblasts - this is leader compound of the obtained series with acceptable in vitro selectivity. Synthesized compounds exhibit antioxidant activity comparable to the reference drug Trolox. Combination of promising antioxidant activity and a selective antitumor cytotoxicity in vitro determines the prospects of these compounds as chemotherapy agents. |
| Databáze: | OpenAIRE |
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