Synthesis, molecular docking, and cytotoxicity of quinazolinone and dihydroquinazolinone derivatives as cytotoxic agents
Abstract Background Cancer is the most cause of morbidity and mortality, and a major public health problem worldwide. In this context, two series of quinazolinone 5a–e and dihydroquinazolinone 10a–f compounds were designed, synthesized as cytotoxic agents. Methodology All derivatives (5a–e and 10a–f...
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| Format: | Article |
| Language: | English |
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BMC
2022-05-01
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| Series: | BMC Chemistry |
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| Online Access: | https://doi.org/10.1186/s13065-022-00825-x |
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| author | Fahimeh Taayoshi Aida Iraji Ali Moazzam Meysam Soleimani Mehdi Asadi Keyvan Pedrood Mosayeb Akbari Hafezeh Salehabadi Bagher Larijani Neda Adibpour Mohammad Mahdavi |
| author_facet | Fahimeh Taayoshi Aida Iraji Ali Moazzam Meysam Soleimani Mehdi Asadi Keyvan Pedrood Mosayeb Akbari Hafezeh Salehabadi Bagher Larijani Neda Adibpour Mohammad Mahdavi |
| author_sort | Fahimeh Taayoshi |
| collection | DOAJ |
| description | Abstract Background Cancer is the most cause of morbidity and mortality, and a major public health problem worldwide. In this context, two series of quinazolinone 5a–e and dihydroquinazolinone 10a–f compounds were designed, synthesized as cytotoxic agents. Methodology All derivatives (5a–e and 10a–f) were synthesized via straightforward pathways and elucidated by FTIR, 1H-NMR, CHNS elemental analysis, as well as the melting point. All the compounds were evaluated for their in vitro cytotoxicity effects using the MTT assay against two human cancer cell lines (MCF-7 and HCT-116) using doxorubicin as the standard drug. The test derivatives were additionally docked into the PARP10 active site using Gold software. Results and discussion Most of the synthesized compounds, especially 5a and 10f were found to be highly potent against both cell lines. Synthesized compounds demonstrated IC50 in the range of 4.87–205.9 μM against HCT-116 cell line and 14.70–98.45 μM against MCF-7 cell line compared with doxorubicin with IC50 values of 1.20 and 1.08 μM after 72 h, respectively, indicated the plausible activities of the synthesized compounds. Conclusion The compounds quinazolinone 5a–e and dihydroquinazolinone 10a–f showed potential activity against cancer cell lines which can lead to rational drug designing of the cytotoxic agents. |
| first_indexed | 2024-04-13T18:37:51Z |
| format | Article |
| id | doaj.art-3eca3a5cd2e94cd8896312810525bfa4 |
| institution | Directory Open Access Journal |
| issn | 2661-801X |
| language | English |
| last_indexed | 2024-04-13T18:37:51Z |
| publishDate | 2022-05-01 |
| publisher | BMC |
| record_format | Article |
| series | BMC Chemistry |
| spelling | doaj.art-3eca3a5cd2e94cd8896312810525bfa42022-12-22T02:34:49ZengBMCBMC Chemistry2661-801X2022-05-0116111210.1186/s13065-022-00825-xSynthesis, molecular docking, and cytotoxicity of quinazolinone and dihydroquinazolinone derivatives as cytotoxic agentsFahimeh Taayoshi0Aida Iraji1Ali Moazzam2Meysam Soleimani3Mehdi Asadi4Keyvan Pedrood5Mosayeb Akbari6Hafezeh Salehabadi7Bagher Larijani8Neda Adibpour9Mohammad Mahdavi10Department of Medicinal Chemistry, School of Pharmacy, Zanjan University of Medical SciencesStem Cells Technology Research Center, Shiraz University of Medical SciencesEndocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical SciencesDepartment of Pharmaceutical Biotechnology, School of Pharmacy, Hamadan University of Medical Science HamadanDepartment of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences, Research Center, Tehran University of Medical SciencesEndocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical SciencesDepartment of Medicinal Chemistry, School of Pharmacy, Zanjan University of Medical SciencesDepartment of Medicinal Chemistry, School of Pharmacy, Zanjan University of Medical SciencesEndocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical SciencesDepartment of Medicinal Chemistry, School of Pharmacy, Zanjan University of Medical SciencesEndocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical SciencesAbstract Background Cancer is the most cause of morbidity and mortality, and a major public health problem worldwide. In this context, two series of quinazolinone 5a–e and dihydroquinazolinone 10a–f compounds were designed, synthesized as cytotoxic agents. Methodology All derivatives (5a–e and 10a–f) were synthesized via straightforward pathways and elucidated by FTIR, 1H-NMR, CHNS elemental analysis, as well as the melting point. All the compounds were evaluated for their in vitro cytotoxicity effects using the MTT assay against two human cancer cell lines (MCF-7 and HCT-116) using doxorubicin as the standard drug. The test derivatives were additionally docked into the PARP10 active site using Gold software. Results and discussion Most of the synthesized compounds, especially 5a and 10f were found to be highly potent against both cell lines. Synthesized compounds demonstrated IC50 in the range of 4.87–205.9 μM against HCT-116 cell line and 14.70–98.45 μM against MCF-7 cell line compared with doxorubicin with IC50 values of 1.20 and 1.08 μM after 72 h, respectively, indicated the plausible activities of the synthesized compounds. Conclusion The compounds quinazolinone 5a–e and dihydroquinazolinone 10a–f showed potential activity against cancer cell lines which can lead to rational drug designing of the cytotoxic agents.https://doi.org/10.1186/s13065-022-00825-xQuinazolinoneDihydroquinazolinone CytotoxicityDockingPARPsSynthesis |
| spellingShingle | Fahimeh Taayoshi Aida Iraji Ali Moazzam Meysam Soleimani Mehdi Asadi Keyvan Pedrood Mosayeb Akbari Hafezeh Salehabadi Bagher Larijani Neda Adibpour Mohammad Mahdavi Synthesis, molecular docking, and cytotoxicity of quinazolinone and dihydroquinazolinone derivatives as cytotoxic agents BMC Chemistry Quinazolinone Dihydroquinazolinone Cytotoxicity Docking PARPs Synthesis |
| title | Synthesis, molecular docking, and cytotoxicity of quinazolinone and dihydroquinazolinone derivatives as cytotoxic agents |
| title_full | Synthesis, molecular docking, and cytotoxicity of quinazolinone and dihydroquinazolinone derivatives as cytotoxic agents |
| title_fullStr | Synthesis, molecular docking, and cytotoxicity of quinazolinone and dihydroquinazolinone derivatives as cytotoxic agents |
| title_full_unstemmed | Synthesis, molecular docking, and cytotoxicity of quinazolinone and dihydroquinazolinone derivatives as cytotoxic agents |
| title_short | Synthesis, molecular docking, and cytotoxicity of quinazolinone and dihydroquinazolinone derivatives as cytotoxic agents |
| title_sort | synthesis molecular docking and cytotoxicity of quinazolinone and dihydroquinazolinone derivatives as cytotoxic agents |
| topic | Quinazolinone Dihydroquinazolinone Cytotoxicity Docking PARPs Synthesis |
| url | https://doi.org/10.1186/s13065-022-00825-x |
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