Novel tetrahydronaphthalen-1-yl-phenethyl ureas: synthesis and dual antibacterial-anticancer activities
Cancer and antibiotic-resistant bacterial infections are significant global health challenges. The resistance developed in cancer treatments intensifies therapeutic difficulties. In addressing these challenges, this study synthesised a series of N,N′-dialkyl urea derivatives containing methoxy subst...
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| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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Taylor & Francis Group
2024-12-01
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| Series: | Journal of Enzyme Inhibition and Medicinal Chemistry |
| Subjects: | |
| Online Access: | https://www.tandfonline.com/doi/10.1080/14756366.2023.2286925 |
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| author | Yusuf Akbaba Fatma Necmiye Kacı Mehmet Enes Arslan Süleyman Göksü Adil Mardinoğlu Hasan Türkez |
| author_facet | Yusuf Akbaba Fatma Necmiye Kacı Mehmet Enes Arslan Süleyman Göksü Adil Mardinoğlu Hasan Türkez |
| author_sort | Yusuf Akbaba |
| collection | DOAJ |
| description | Cancer and antibiotic-resistant bacterial infections are significant global health challenges. The resistance developed in cancer treatments intensifies therapeutic difficulties. In addressing these challenges, this study synthesised a series of N,N′-dialkyl urea derivatives containing methoxy substituents on phenethylamines. Using isocyanate for the efficient synthesis yielded target products 14–18 in 73–76% returns. Subsequently, their antibacterial and anticancer potentials were assessed. Cytotoxicity tests on cancer cell lines, bacterial strains, and a healthy fibroblast line revealed promising outcomes. All derivatives demonstrated robust antibacterial activity, with MIC values ranging from 0.97 to 15.82 µM. Notably, compounds 14 and 16 were particularly effective against the HeLa cell line, while compounds 14, 15, and 17 showed significant activity against the SH-SY5Y cell line. Importantly, these compounds had reduced toxicity to healthy fibroblast cells than to cancer cells, suggesting their potential as dual-functioning agents targeting both cancer and bacterial infections. |
| format | Article |
| id | doaj-art-0c37fa8d10d0402b84cadf89b95d45a7 |
| institution | Kabale University |
| issn | 1475-6366 1475-6374 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Journal of Enzyme Inhibition and Medicinal Chemistry |
| spelling | doaj-art-0c37fa8d10d0402b84cadf89b95d45a72024-12-26T09:30:44ZengTaylor & Francis GroupJournal of Enzyme Inhibition and Medicinal Chemistry1475-63661475-63742024-12-0139110.1080/14756366.2023.2286925Novel tetrahydronaphthalen-1-yl-phenethyl ureas: synthesis and dual antibacterial-anticancer activitiesYusuf Akbaba0Fatma Necmiye Kacı1Mehmet Enes Arslan2Süleyman Göksü3Adil Mardinoğlu4Hasan Türkez5Department of Basic Sciences, Faculty of Science, Erzurum Technical University, Erzurum, TurkeyDepartment of Molecular Biology & Genetics, Faculty of Science, Erzurum Technical University, Erzurum, TurkeyDepartment of Molecular Biology and Genetics, Faculty of Science, Erzurum Technical University, Erzurum, TurkeyDepartment of Chemistry, Faculty of Science, Atatürk University, Erzurum, TurkeyScience for Life Laboratory, KTH-Royal Institute of Technology, Stockholm, SwedenDepartment of Medical Biology, Faculty of Medicine, Atatürk University, Erzurum, TurkeyCancer and antibiotic-resistant bacterial infections are significant global health challenges. The resistance developed in cancer treatments intensifies therapeutic difficulties. In addressing these challenges, this study synthesised a series of N,N′-dialkyl urea derivatives containing methoxy substituents on phenethylamines. Using isocyanate for the efficient synthesis yielded target products 14–18 in 73–76% returns. Subsequently, their antibacterial and anticancer potentials were assessed. Cytotoxicity tests on cancer cell lines, bacterial strains, and a healthy fibroblast line revealed promising outcomes. All derivatives demonstrated robust antibacterial activity, with MIC values ranging from 0.97 to 15.82 µM. Notably, compounds 14 and 16 were particularly effective against the HeLa cell line, while compounds 14, 15, and 17 showed significant activity against the SH-SY5Y cell line. Importantly, these compounds had reduced toxicity to healthy fibroblast cells than to cancer cells, suggesting their potential as dual-functioning agents targeting both cancer and bacterial infections.https://www.tandfonline.com/doi/10.1080/14756366.2023.2286925Antibacterial activityanticancer activityisocyanatesN,N′-dialkyl ureaphenethylamine |
| spellingShingle | Yusuf Akbaba Fatma Necmiye Kacı Mehmet Enes Arslan Süleyman Göksü Adil Mardinoğlu Hasan Türkez Novel tetrahydronaphthalen-1-yl-phenethyl ureas: synthesis and dual antibacterial-anticancer activities Journal of Enzyme Inhibition and Medicinal Chemistry Antibacterial activity anticancer activity isocyanates N,N′-dialkyl urea phenethylamine |
| title | Novel tetrahydronaphthalen-1-yl-phenethyl ureas: synthesis and dual antibacterial-anticancer activities |
| title_full | Novel tetrahydronaphthalen-1-yl-phenethyl ureas: synthesis and dual antibacterial-anticancer activities |
| title_fullStr | Novel tetrahydronaphthalen-1-yl-phenethyl ureas: synthesis and dual antibacterial-anticancer activities |
| title_full_unstemmed | Novel tetrahydronaphthalen-1-yl-phenethyl ureas: synthesis and dual antibacterial-anticancer activities |
| title_short | Novel tetrahydronaphthalen-1-yl-phenethyl ureas: synthesis and dual antibacterial-anticancer activities |
| title_sort | novel tetrahydronaphthalen 1 yl phenethyl ureas synthesis and dual antibacterial anticancer activities |
| topic | Antibacterial activity anticancer activity isocyanates N,N′-dialkyl urea phenethylamine |
| url | https://www.tandfonline.com/doi/10.1080/14756366.2023.2286925 |
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