Microwave-assisted synthesis, characterization, and molecular docking studies of new chlorophthalazine derivatives as anticancer activity
A series of phthalazine derivatives have been synthesized using green protocol methods under microwave irradiation. This involved subjecting chlorophthalazine to microwave irradiation and employing various reagents, including hydrazine derivatives, primary and secondary amines, and active methylene,...
Saved in:
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Taylor & Francis Group
2024-12-01
|
| Series: | Arab Journal of Basic and Applied Sciences |
| Subjects: | |
| Online Access: | https://www.tandfonline.com/doi/10.1080/25765299.2024.2387383 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1846118974781128704 |
|---|---|
| author | Samar A. Abubshait Rasha J. Almalih Haya A. Abubshait Mohamed S. Gomaa Ashraf N. Abdalla |
| author_facet | Samar A. Abubshait Rasha J. Almalih Haya A. Abubshait Mohamed S. Gomaa Ashraf N. Abdalla |
| author_sort | Samar A. Abubshait |
| collection | DOAJ |
| description | A series of phthalazine derivatives have been synthesized using green protocol methods under microwave irradiation. This involved subjecting chlorophthalazine to microwave irradiation and employing various reagents, including hydrazine derivatives, primary and secondary amines, and active methylene, to generate the novel phthalazine derivatives. Subsequently, a comparison was made between the yield percentage and reaction time of the resulting products obtained from conventional methods and those obtained through microwave irradiation. The structures of all new compounds were confirmed by physical properties and spectral analysis. The phthalazine compounds demonstrated significant anticancer activity against three cancer cell lines and showed promising selectivity when compared with doxorubicin. Compound 6 exhibited the best anticancer activity, with IC50 1.739 µM, 0.384 µM, and 1.52 µM against MCF7, HCT116, and HepG2 cell lines, respectively. The docking results confirmed that the drugs exert their activity by inhibiting PARP-1. The binding scores were in accordance with the experimental IC50, with compound 6 exhibiting the best binding score and retaining the essential binding interactions with the active site. The results of our computational research have revealed that our phthalazine compounds possess a unique structure that effectively inhibits PARP-1. |
| format | Article |
| id | doaj-art-8421861c4e404783b4f52cd0b93dcae1 |
| institution | Kabale University |
| issn | 2576-5299 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Arab Journal of Basic and Applied Sciences |
| spelling | doaj-art-8421861c4e404783b4f52cd0b93dcae12024-12-17T08:04:46ZengTaylor & Francis GroupArab Journal of Basic and Applied Sciences2576-52992024-12-0131145446910.1080/25765299.2024.2387383Microwave-assisted synthesis, characterization, and molecular docking studies of new chlorophthalazine derivatives as anticancer activitySamar A. Abubshait0Rasha J. Almalih1Haya A. Abubshait2Mohamed S. Gomaa3Ashraf N. Abdalla4Department of Chemistry, College of Science, Imam Abdulrahman Bin Faisal University, Dammam, Saudi ArabiaBasic and Applied Scientific Research Center, Imam Abdulrahman Bin Faisal University, Dammam, Saudi ArabiaBasic Sciences Department, Deanship of Preparatory Year and Supporting Studies, Imam Abdulrahman Bin Faisal University, Dammam, Saudi ArabiaDepartment of Pharmaceutical Chemistry, College of Clinical Pharmacy, Imam Abdulrahman Bin Faisal University, Dammam, Saudi ArabiaDepartment of Pharmacology and Toxicology, College of Pharmacy, Umm Al-Qura University, Makkah, Saudi ArabiaA series of phthalazine derivatives have been synthesized using green protocol methods under microwave irradiation. This involved subjecting chlorophthalazine to microwave irradiation and employing various reagents, including hydrazine derivatives, primary and secondary amines, and active methylene, to generate the novel phthalazine derivatives. Subsequently, a comparison was made between the yield percentage and reaction time of the resulting products obtained from conventional methods and those obtained through microwave irradiation. The structures of all new compounds were confirmed by physical properties and spectral analysis. The phthalazine compounds demonstrated significant anticancer activity against three cancer cell lines and showed promising selectivity when compared with doxorubicin. Compound 6 exhibited the best anticancer activity, with IC50 1.739 µM, 0.384 µM, and 1.52 µM against MCF7, HCT116, and HepG2 cell lines, respectively. The docking results confirmed that the drugs exert their activity by inhibiting PARP-1. The binding scores were in accordance with the experimental IC50, with compound 6 exhibiting the best binding score and retaining the essential binding interactions with the active site. The results of our computational research have revealed that our phthalazine compounds possess a unique structure that effectively inhibits PARP-1.https://www.tandfonline.com/doi/10.1080/25765299.2024.2387383Anticancer activitychlorophthalazine derivativesmicrowave-assistedmolecular docking studyphthalazine derivativesone-pot reactions |
| spellingShingle | Samar A. Abubshait Rasha J. Almalih Haya A. Abubshait Mohamed S. Gomaa Ashraf N. Abdalla Microwave-assisted synthesis, characterization, and molecular docking studies of new chlorophthalazine derivatives as anticancer activity Arab Journal of Basic and Applied Sciences Anticancer activity chlorophthalazine derivatives microwave-assisted molecular docking study phthalazine derivatives one-pot reactions |
| title | Microwave-assisted synthesis, characterization, and molecular docking studies of new chlorophthalazine derivatives as anticancer activity |
| title_full | Microwave-assisted synthesis, characterization, and molecular docking studies of new chlorophthalazine derivatives as anticancer activity |
| title_fullStr | Microwave-assisted synthesis, characterization, and molecular docking studies of new chlorophthalazine derivatives as anticancer activity |
| title_full_unstemmed | Microwave-assisted synthesis, characterization, and molecular docking studies of new chlorophthalazine derivatives as anticancer activity |
| title_short | Microwave-assisted synthesis, characterization, and molecular docking studies of new chlorophthalazine derivatives as anticancer activity |
| title_sort | microwave assisted synthesis characterization and molecular docking studies of new chlorophthalazine derivatives as anticancer activity |
| topic | Anticancer activity chlorophthalazine derivatives microwave-assisted molecular docking study phthalazine derivatives one-pot reactions |
| url | https://www.tandfonline.com/doi/10.1080/25765299.2024.2387383 |
| work_keys_str_mv | AT samaraabubshait microwaveassistedsynthesischaracterizationandmoleculardockingstudiesofnewchlorophthalazinederivativesasanticanceractivity AT rashajalmalih microwaveassistedsynthesischaracterizationandmoleculardockingstudiesofnewchlorophthalazinederivativesasanticanceractivity AT hayaaabubshait microwaveassistedsynthesischaracterizationandmoleculardockingstudiesofnewchlorophthalazinederivativesasanticanceractivity AT mohamedsgomaa microwaveassistedsynthesischaracterizationandmoleculardockingstudiesofnewchlorophthalazinederivativesasanticanceractivity AT ashrafnabdalla microwaveassistedsynthesischaracterizationandmoleculardockingstudiesofnewchlorophthalazinederivativesasanticanceractivity |