Synthesis, X-Ray Crystal Structures, and Preliminary Antiproliferative Activities of New s-Triazine-hydroxybenzylidene Hydrazone Derivatives
We herein report a new small library of Schiff-base compounds that encompasses s-triazine and (2 or 4)-hydroxylbenzylidene derivatives. These compounds were synthesized through a hydrazone linkage connecting both the s-triazine and hydroxybenzylidene derivatives. The synthetic strategy adopted allow...
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| Format: | Article |
| Language: | English |
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Wiley
2019-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2019/9403908 |
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| author | Assem Barakat Fardous F. El-Senduny Zainab Almarhoon Hessa H. Al-Rasheed Farid A. Badria Abdullah Mohammed Al-Majid Hazem A. Ghabbour Ayman El-Faham |
| author_facet | Assem Barakat Fardous F. El-Senduny Zainab Almarhoon Hessa H. Al-Rasheed Farid A. Badria Abdullah Mohammed Al-Majid Hazem A. Ghabbour Ayman El-Faham |
| author_sort | Assem Barakat |
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| description | We herein report a new small library of Schiff-base compounds that encompasses s-triazine and (2 or 4)-hydroxylbenzylidene derivatives. These compounds were synthesized through a hydrazone linkage connecting both the s-triazine and hydroxybenzylidene derivatives. The synthetic strategy adopted allowed the synthesis of the target compounds with excellent yields and purities as observed from their NMR (1H and 13C) and elemental analysis. Furthermore, 4f, 5b, and 5f were further confirmed by X-ray single crystal diffraction technique. The preliminary antiproliferative activities for the synthesized compounds were tested against two different cancer cell lines including breast cancer (MCF-7) and colon cancer (HCT-116). From the eighteen compounds, which have been examined, only two derivatives having piperidine moiety showed more selectivity against the two cell lines MCF-7 and HCT-116, while the others showed very weak activity. The position of the hydroxyl group in the benzylidine ring and the substituent on the s-triazine moiety has great effect on the activity of the prepared compounds. The IC50 values for the two derivatives 4a and 5a evaluated against breast cancer cells, very close to those for the chemotherapeutic drug cisplatin, are 27 µM (13.3 µg/mL), 17 µM (8.4 µg/mL), and 20 µM (6 µg/mL) for 4a, 5a, and cisplatin, respectively. These results propose the preliminary antiproliferative activity of these two derivatives may deserve further consideration for development of new derivatives as potent anticancer agents. |
| format | Article |
| id | doaj-art-c3a06a5ba8e04f049d578eb81988d903 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2019-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-c3a06a5ba8e04f049d578eb81988d9032025-02-03T06:42:18ZengWileyJournal of Chemistry2090-90632090-90712019-01-01201910.1155/2019/94039089403908Synthesis, X-Ray Crystal Structures, and Preliminary Antiproliferative Activities of New s-Triazine-hydroxybenzylidene Hydrazone DerivativesAssem Barakat0Fardous F. El-Senduny1Zainab Almarhoon2Hessa H. Al-Rasheed3Farid A. Badria4Abdullah Mohammed Al-Majid5Hazem A. Ghabbour6Ayman El-Faham7Chemistry Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Mansura University, Mansura 35516, EgyptChemistry Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaChemistry Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Pharmacognosy, Faculty of Pharmacy, Mansura University, Mansura 35516, EgyptChemistry Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Medicinal Chemistry, Faculty of Pharmacy, Mansura University, Mansoura 35516, EgyptChemistry Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaWe herein report a new small library of Schiff-base compounds that encompasses s-triazine and (2 or 4)-hydroxylbenzylidene derivatives. These compounds were synthesized through a hydrazone linkage connecting both the s-triazine and hydroxybenzylidene derivatives. The synthetic strategy adopted allowed the synthesis of the target compounds with excellent yields and purities as observed from their NMR (1H and 13C) and elemental analysis. Furthermore, 4f, 5b, and 5f were further confirmed by X-ray single crystal diffraction technique. The preliminary antiproliferative activities for the synthesized compounds were tested against two different cancer cell lines including breast cancer (MCF-7) and colon cancer (HCT-116). From the eighteen compounds, which have been examined, only two derivatives having piperidine moiety showed more selectivity against the two cell lines MCF-7 and HCT-116, while the others showed very weak activity. The position of the hydroxyl group in the benzylidine ring and the substituent on the s-triazine moiety has great effect on the activity of the prepared compounds. The IC50 values for the two derivatives 4a and 5a evaluated against breast cancer cells, very close to those for the chemotherapeutic drug cisplatin, are 27 µM (13.3 µg/mL), 17 µM (8.4 µg/mL), and 20 µM (6 µg/mL) for 4a, 5a, and cisplatin, respectively. These results propose the preliminary antiproliferative activity of these two derivatives may deserve further consideration for development of new derivatives as potent anticancer agents.http://dx.doi.org/10.1155/2019/9403908 |
| spellingShingle | Assem Barakat Fardous F. El-Senduny Zainab Almarhoon Hessa H. Al-Rasheed Farid A. Badria Abdullah Mohammed Al-Majid Hazem A. Ghabbour Ayman El-Faham Synthesis, X-Ray Crystal Structures, and Preliminary Antiproliferative Activities of New s-Triazine-hydroxybenzylidene Hydrazone Derivatives Journal of Chemistry |
| title | Synthesis, X-Ray Crystal Structures, and Preliminary Antiproliferative Activities of New s-Triazine-hydroxybenzylidene Hydrazone Derivatives |
| title_full | Synthesis, X-Ray Crystal Structures, and Preliminary Antiproliferative Activities of New s-Triazine-hydroxybenzylidene Hydrazone Derivatives |
| title_fullStr | Synthesis, X-Ray Crystal Structures, and Preliminary Antiproliferative Activities of New s-Triazine-hydroxybenzylidene Hydrazone Derivatives |
| title_full_unstemmed | Synthesis, X-Ray Crystal Structures, and Preliminary Antiproliferative Activities of New s-Triazine-hydroxybenzylidene Hydrazone Derivatives |
| title_short | Synthesis, X-Ray Crystal Structures, and Preliminary Antiproliferative Activities of New s-Triazine-hydroxybenzylidene Hydrazone Derivatives |
| title_sort | synthesis x ray crystal structures and preliminary antiproliferative activities of new s triazine hydroxybenzylidene hydrazone derivatives |
| url | http://dx.doi.org/10.1155/2019/9403908 |
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