Anti-proliferative and morphological studies of 2-(benzo[d]thiazol-2-yl) derivatives together with their strategy in ionic liquids immobilized reactions
Abstract In this work, an efficient and expeditious synthesis of a series of new benzo[d]thiazole derivatives has been reported starting from the reaction of 2-aminothiophenol with different esters such as ethyl cyanoacetate, diethylmalonate or ethyl acetoacetate to produce benzo[d]thiazole derivatives. The latter compounds underwent multi-component reactions with aromatic aldehydes and cyclohexan-1,3-dione using two different conditions first the use of solvent and regular catalyst and secondly using solvent free ionic liquids immobilized multi-component was studied. Comparison between the yields in the two methods was recorded. The benzo[d]thiazole derivatives were characterized by extensive analytical and spectral studies and were further used as starting materials for some heterocyclic transformations to produce biologically active compounds. Most of the tested compounds exhibited high cytotoxicity except few compounds. All tested compounds exhibited greater inhibitory action than the reference drug Doxorubicin against HeLa cell line except six compounds. The most cytotoxic compounds were 8h, 10e, 12b, 12i, 14b, 14h, 14i and 15i with $ IC_{50} $’s 0.21, 0.26, 0.32, 0.19, 0.32, 0.27, 0.25 and 0.18 µM, respectively against HepG2 cell line. In addition, the majority of the tested compounds emerged as c-MET kinase and PC-3 cell inhibitors which revealed that most of the tested compounds showed from moderate to good inhibitions..
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:21 |
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| Enthalten in: |
Journal of the Iranian Chemical Society - 21(2024), 4 vom: 19. März, Seite 921-942 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Mohareb, Rafat M. [VerfasserIn] |
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| Links: |
Volltext [lizenzpflichtig] |
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| BKL: | |
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| Themen: |
]thiazole |
| Anmerkungen: |
© Iranian Chemical Society 2024. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. |
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| doi: |
10.1007/s13738-023-02956-x |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 520 | |a Abstract In this work, an efficient and expeditious synthesis of a series of new benzo[d]thiazole derivatives has been reported starting from the reaction of 2-aminothiophenol with different esters such as ethyl cyanoacetate, diethylmalonate or ethyl acetoacetate to produce benzo[d]thiazole derivatives. The latter compounds underwent multi-component reactions with aromatic aldehydes and cyclohexan-1,3-dione using two different conditions first the use of solvent and regular catalyst and secondly using solvent free ionic liquids immobilized multi-component was studied. Comparison between the yields in the two methods was recorded. The benzo[d]thiazole derivatives were characterized by extensive analytical and spectral studies and were further used as starting materials for some heterocyclic transformations to produce biologically active compounds. Most of the tested compounds exhibited high cytotoxicity except few compounds. All tested compounds exhibited greater inhibitory action than the reference drug Doxorubicin against HeLa cell line except six compounds. The most cytotoxic compounds were 8h, 10e, 12b, 12i, 14b, 14h, 14i and 15i with $ IC_{50} $’s 0.21, 0.26, 0.32, 0.19, 0.32, 0.27, 0.25 and 0.18 µM, respectively against HepG2 cell line. In addition, the majority of the tested compounds emerged as c-MET kinase and PC-3 cell inhibitors which revealed that most of the tested compounds showed from moderate to good inhibitions. | ||
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| 650 | 4 | |a Ionic liquids immobilized catalyst |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Cytotoxicity |7 (dpeaa)DE-He213 | |
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