2-Alkyl(aryl)-quinazolin-4(3H)-thiones, 2-R-(quinazolin-4(3H)-ylthio)carboxylic acids and amides: synthesis,molecular docking,antimicrobial and anticancer properties |
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| Authors: | Lyudmyla Antypenko Sergiy Kovalenko Yulia Posylkina Vladyslav Nikitin Natalia Fedyunina Vitalii Ivchuk |
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| Affiliation: | 1. Department of Organic and Bioorganic Chemistry, Zaporizhzya State Medical University, Zaporizhzhya, Ukraine, antypenkol@gmail.com;3. Department of Organic and Bioorganic Chemistry, Zaporizhzya State Medical University, Zaporizhzhya, Ukraine,;4. Enamine Ltd., Kyiv, Ukraine,;5. Bacterial Laboratory, Zaporizhzhya Regional Hospital, Zaporizhzhya, Ukraine, and;6. Department of Chemistry, Kryvyi Rih National University, Kryvyi Rih, Ukraine |
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| Abstract: | In this study, a series of novel 2-alkyl(aryl)-quinazolin-4(3H)-thiones, 2-R-(quinazolin-4(3H)-ylthio)carboxylic acids and amides were synthesized and evaluated for antimicrobial and anticancer activities. Their structure was confirmed by elemental analysis and spectral data (FT-IR, LC-MS, 1H-NMR). Antimicrobial activity was tested in vitro against Staphylococcus aureus, Enterococcus faecalis, Enterobacter aerogenes, Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumonia, Candida albicans and NCI in vitro preliminary anticancer activity against nine different cancer types. The most active antibacterial and antifungal compounds were: 2.1, 2.2 and 2.4. The introduction of the carboxylic acid or amide residue into the fourth position of quinazolin-4(3H)-thione resulted in the absence of antimicrobial activity. Substance 3.8 inhibited renal cancer UO-31 line and 2.18 – leukemia CCRF-CEM. The results of in silico molecular docking for DHFR and CK2 kinase had no correlation with in vitro properties, proposing the presence of other biological activity pathways. |
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| Keywords: | 2-Alkyl(aryl)-quinazolin-4(3H)-thiones antibiotic anticancer antifungal molecular docking |
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