Cargando…
Synthesis, molecular docking, and cytotoxicity of quinazolinone and dihydroquinazolinone derivatives as cytotoxic agents
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...
Autores principales: | , , , , , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Springer International Publishing
2022
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9118628/ https://www.ncbi.nlm.nih.gov/pubmed/35585608 http://dx.doi.org/10.1186/s13065-022-00825-x |
_version_ | 1784710537897050112 |
---|---|
author | Taayoshi, Fahimeh Iraji, Aida Moazzam, Ali Soleimani, Meysam Asadi, Mehdi Pedrood, Keyvan Akbari, Mosayeb Salehabadi, Hafezeh Larijani, Bagher Adibpour, Neda Mahdavi, Mohammad |
author_facet | Taayoshi, Fahimeh Iraji, Aida Moazzam, Ali Soleimani, Meysam Asadi, Mehdi Pedrood, Keyvan Akbari, Mosayeb Salehabadi, Hafezeh Larijani, Bagher Adibpour, Neda Mahdavi, Mohammad |
author_sort | Taayoshi, Fahimeh |
collection | PubMed |
description | 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, (1)H-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 IC(50) 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 IC(50) 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. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1186/s13065-022-00825-x. |
format | Online Article Text |
id | pubmed-9118628 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Springer International Publishing |
record_format | MEDLINE/PubMed |
spelling | pubmed-91186282022-05-20 Synthesis, molecular docking, and cytotoxicity of quinazolinone and dihydroquinazolinone derivatives as cytotoxic agents Taayoshi, Fahimeh Iraji, Aida Moazzam, Ali Soleimani, Meysam Asadi, Mehdi Pedrood, Keyvan Akbari, Mosayeb Salehabadi, Hafezeh Larijani, Bagher Adibpour, Neda Mahdavi, Mohammad BMC Chem Research 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, (1)H-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 IC(50) 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 IC(50) 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. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1186/s13065-022-00825-x. Springer International Publishing 2022-05-18 /pmc/articles/PMC9118628/ /pubmed/35585608 http://dx.doi.org/10.1186/s13065-022-00825-x Text en © The Author(s) 2022 https://creativecommons.org/licenses/by/4.0/Open AccessThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) . The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/ (https://creativecommons.org/publicdomain/zero/1.0/) ) applies to the data made available in this article, unless otherwise stated in a credit line to the data. |
spellingShingle | Research Taayoshi, Fahimeh Iraji, Aida Moazzam, Ali Soleimani, Meysam Asadi, Mehdi Pedrood, Keyvan Akbari, Mosayeb Salehabadi, Hafezeh Larijani, Bagher Adibpour, Neda Mahdavi, Mohammad Synthesis, molecular docking, and cytotoxicity of quinazolinone and dihydroquinazolinone derivatives as cytotoxic agents |
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 | Research |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9118628/ https://www.ncbi.nlm.nih.gov/pubmed/35585608 http://dx.doi.org/10.1186/s13065-022-00825-x |
work_keys_str_mv | AT taayoshifahimeh synthesismoleculardockingandcytotoxicityofquinazolinoneanddihydroquinazolinonederivativesascytotoxicagents AT irajiaida synthesismoleculardockingandcytotoxicityofquinazolinoneanddihydroquinazolinonederivativesascytotoxicagents AT moazzamali synthesismoleculardockingandcytotoxicityofquinazolinoneanddihydroquinazolinonederivativesascytotoxicagents AT soleimanimeysam synthesismoleculardockingandcytotoxicityofquinazolinoneanddihydroquinazolinonederivativesascytotoxicagents AT asadimehdi synthesismoleculardockingandcytotoxicityofquinazolinoneanddihydroquinazolinonederivativesascytotoxicagents AT pedroodkeyvan synthesismoleculardockingandcytotoxicityofquinazolinoneanddihydroquinazolinonederivativesascytotoxicagents AT akbarimosayeb synthesismoleculardockingandcytotoxicityofquinazolinoneanddihydroquinazolinonederivativesascytotoxicagents AT salehabadihafezeh synthesismoleculardockingandcytotoxicityofquinazolinoneanddihydroquinazolinonederivativesascytotoxicagents AT larijanibagher synthesismoleculardockingandcytotoxicityofquinazolinoneanddihydroquinazolinonederivativesascytotoxicagents AT adibpourneda synthesismoleculardockingandcytotoxicityofquinazolinoneanddihydroquinazolinonederivativesascytotoxicagents AT mahdavimohammad synthesismoleculardockingandcytotoxicityofquinazolinoneanddihydroquinazolinonederivativesascytotoxicagents |