Synthesis and Cytotoxic Activity of Chiral Sulfonamides Based on the 2-Azabicycloalkane Skeleton
A series of chiral sulfonamides containing the 2-azabicycloalkane scaffold were prepared from <i>aza</i>-Diels–Alder cycloadducts through their conversion to amines based on 2-azanorbornane or the bridged azepane skeleton, followed by the reaction with sulfonyl chlorides. The cytotoxic a...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/10/2355 |
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| author | Mahzeiar Samadaei Matthias Pinter Daniel Senfter Sibylle Madlener Nataliya Rohr-Udilova Dominika Iwan Karolina Kamińska Elżbieta Wojaczyńska Jacek Wojaczyński Andrzej Kochel |
| author_facet | Mahzeiar Samadaei Matthias Pinter Daniel Senfter Sibylle Madlener Nataliya Rohr-Udilova Dominika Iwan Karolina Kamińska Elżbieta Wojaczyńska Jacek Wojaczyński Andrzej Kochel |
| author_sort | Mahzeiar Samadaei |
| collection | DOAJ |
| description | A series of chiral sulfonamides containing the 2-azabicycloalkane scaffold were prepared from <i>aza</i>-Diels–Alder cycloadducts through their conversion to amines based on 2-azanorbornane or the bridged azepane skeleton, followed by the reaction with sulfonyl chlorides. The cytotoxic activity of the obtained bicyclic derivatives was evaluated using human hepatocellular carcinoma (HCC), medulloblastoma (MB), and glioblastoma (GBM) cell lines. Chosen compounds were shown to notably reduce cell viability as compared to nonmalignant cells. |
| first_indexed | 2024-03-10T19:44:51Z |
| format | Article |
| id | doaj.art-7843616b6b864dabb356826046da066c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T19:44:51Z |
| publishDate | 2020-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-7843616b6b864dabb356826046da066c2023-11-20T00:53:02ZengMDPI AGMolecules1420-30492020-05-012510235510.3390/molecules25102355Synthesis and Cytotoxic Activity of Chiral Sulfonamides Based on the 2-Azabicycloalkane SkeletonMahzeiar Samadaei0Matthias Pinter1Daniel Senfter2Sibylle Madlener3Nataliya Rohr-Udilova4Dominika Iwan5Karolina Kamińska6Elżbieta Wojaczyńska7Jacek Wojaczyński8Andrzej Kochel9Department of Internal Medicine III, Medical University of Vienna, AKH Vienna Währinger Gürtel 18-20, 1090 Vienna, AustriaDepartment of Internal Medicine III, Medical University of Vienna, AKH Vienna Währinger Gürtel 18-20, 1090 Vienna, AustriaDepartment of Internal Medicine III, Medical University of Vienna, AKH Vienna Währinger Gürtel 18-20, 1090 Vienna, AustriaDepartment of Internal Medicine III, Medical University of Vienna, AKH Vienna Währinger Gürtel 18-20, 1090 Vienna, AustriaDepartment of Internal Medicine III, Medical University of Vienna, AKH Vienna Währinger Gürtel 18-20, 1090 Vienna, AustriaFaculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, PolandFaculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, PolandFaculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, PolandFaculty of Chemistry, University of Wrocław, F. Joliot-Curie St. 14, 50-383 Wrocław, PolandFaculty of Chemistry, University of Wrocław, F. Joliot-Curie St. 14, 50-383 Wrocław, PolandA series of chiral sulfonamides containing the 2-azabicycloalkane scaffold were prepared from <i>aza</i>-Diels–Alder cycloadducts through their conversion to amines based on 2-azanorbornane or the bridged azepane skeleton, followed by the reaction with sulfonyl chlorides. The cytotoxic activity of the obtained bicyclic derivatives was evaluated using human hepatocellular carcinoma (HCC), medulloblastoma (MB), and glioblastoma (GBM) cell lines. Chosen compounds were shown to notably reduce cell viability as compared to nonmalignant cells.https://www.mdpi.com/1420-3049/25/10/23552-azabicycloalkanechiral sulfonamidecytotoxic activity |
| spellingShingle | Mahzeiar Samadaei Matthias Pinter Daniel Senfter Sibylle Madlener Nataliya Rohr-Udilova Dominika Iwan Karolina Kamińska Elżbieta Wojaczyńska Jacek Wojaczyński Andrzej Kochel Synthesis and Cytotoxic Activity of Chiral Sulfonamides Based on the 2-Azabicycloalkane Skeleton Molecules 2-azabicycloalkane chiral sulfonamide cytotoxic activity |
| title | Synthesis and Cytotoxic Activity of Chiral Sulfonamides Based on the 2-Azabicycloalkane Skeleton |
| title_full | Synthesis and Cytotoxic Activity of Chiral Sulfonamides Based on the 2-Azabicycloalkane Skeleton |
| title_fullStr | Synthesis and Cytotoxic Activity of Chiral Sulfonamides Based on the 2-Azabicycloalkane Skeleton |
| title_full_unstemmed | Synthesis and Cytotoxic Activity of Chiral Sulfonamides Based on the 2-Azabicycloalkane Skeleton |
| title_short | Synthesis and Cytotoxic Activity of Chiral Sulfonamides Based on the 2-Azabicycloalkane Skeleton |
| title_sort | synthesis and cytotoxic activity of chiral sulfonamides based on the 2 azabicycloalkane skeleton |
| topic | 2-azabicycloalkane chiral sulfonamide cytotoxic activity |
| url | https://www.mdpi.com/1420-3049/25/10/2355 |
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