Fe3O4@SiO2-SnCl4-promoted synthesis, cytotoxic evaluation, molecular docking, and MD simulation of some indenopyrido[2,3-d]pyrimidine derivatives
Abstract In this study, an efficient and environmentally friendly method for the one-pot synthesis of indenopyrido[2,3-d]pyrimidine derivatives was developed using Fe3O4@SiO2-SnCl4 nanoparticles as a catalyst. Indenopyrido[2,3-d]pyrimidines (4a-4j) were synthesized via three-component couplings of 6...
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2025-05-01
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| Online Access: | https://doi.org/10.1186/s13065-025-01489-z |
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| author | Leila Emami Ladan Baziyar Al-Anood Mohammad Al-Dies Sara Sadeghian Bi Bi Fatemeh Mirjalili Zeinab Faghih Sajad Khorasani Leila Zamani Soghra Khabnadideh |
| author_facet | Leila Emami Ladan Baziyar Al-Anood Mohammad Al-Dies Sara Sadeghian Bi Bi Fatemeh Mirjalili Zeinab Faghih Sajad Khorasani Leila Zamani Soghra Khabnadideh |
| author_sort | Leila Emami |
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| description | Abstract In this study, an efficient and environmentally friendly method for the one-pot synthesis of indenopyrido[2,3-d]pyrimidine derivatives was developed using Fe3O4@SiO2-SnCl4 nanoparticles as a catalyst. Indenopyrido[2,3-d]pyrimidines (4a-4j) were synthesized via three-component couplings of 6-amino-2-(methylthio)pyrimidin-4(3H)-one, 1,3-indanedione, and aldehydes in water as the solvent. In this reaction, Fe3O4@SiO2–SnCl4 demonstrated a highly catalytic nature, an easy handling procedure, short reaction times, recyclability exploitation, and excellent yields. The cytotoxic activities of the synthesized indenopyrido[2,3-d] pyrimidines analogues were evaluated against three cancer cell lines; MCF-7 (breast carcinoma), A549 (lung non-small cell carcinoma), and SKOV3 (ovarian carcinoma) using MTT assay. Additionally, molecular docking studies and molecular dynamics (MD) simulation of the investigated compounds was performed to verify their binding modes toward EGFR kinase receptor as the possible targets. This analysis aimed to predict the antitumor mechanisms of the synthesized compounds. The binding free energy values of the compounds showed a satisfactory correlation with their cytotoxic activities. |
| format | Article |
| id | doaj-art-a7dfe0cbe4f747efb59657aba119318f |
| institution | OA Journals |
| issn | 2661-801X |
| language | English |
| publishDate | 2025-05-01 |
| publisher | BMC |
| record_format | Article |
| series | BMC Chemistry |
| spelling | doaj-art-a7dfe0cbe4f747efb59657aba119318f2025-08-20T02:32:00ZengBMCBMC Chemistry2661-801X2025-05-0119111310.1186/s13065-025-01489-zFe3O4@SiO2-SnCl4-promoted synthesis, cytotoxic evaluation, molecular docking, and MD simulation of some indenopyrido[2,3-d]pyrimidine derivativesLeila Emami0Ladan Baziyar1Al-Anood Mohammad Al-Dies2Sara Sadeghian3Bi Bi Fatemeh Mirjalili4Zeinab Faghih5Sajad Khorasani6Leila Zamani7Soghra Khabnadideh8Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Shiraz University of Medical SciencesDepartment of Medicinal Chemistry, Faculty of Pharmacy, Shiraz University of Medical SciencesDepartment of Chemistry, Al Qunfudah University College, UMM Al-Qura UniversityDepartment of Medicinal Chemistry, Faculty of Pharmacy, Shiraz University of Medical SciencesDepartment of Chemistry, College of Science, Yazd UniversityPharmaceutical Sciences Research Center, Faculty of Pharmacy, Shiraz University of Medical SciencesPharmaceutical Sciences Research Center, Faculty of Pharmacy, Shiraz University of Medical SciencesPharmaceutical Sciences Research Center, Faculty of Pharmacy, Shiraz University of Medical SciencesPharmaceutical Sciences Research Center, Faculty of Pharmacy, Shiraz University of Medical SciencesAbstract In this study, an efficient and environmentally friendly method for the one-pot synthesis of indenopyrido[2,3-d]pyrimidine derivatives was developed using Fe3O4@SiO2-SnCl4 nanoparticles as a catalyst. Indenopyrido[2,3-d]pyrimidines (4a-4j) were synthesized via three-component couplings of 6-amino-2-(methylthio)pyrimidin-4(3H)-one, 1,3-indanedione, and aldehydes in water as the solvent. In this reaction, Fe3O4@SiO2–SnCl4 demonstrated a highly catalytic nature, an easy handling procedure, short reaction times, recyclability exploitation, and excellent yields. The cytotoxic activities of the synthesized indenopyrido[2,3-d] pyrimidines analogues were evaluated against three cancer cell lines; MCF-7 (breast carcinoma), A549 (lung non-small cell carcinoma), and SKOV3 (ovarian carcinoma) using MTT assay. Additionally, molecular docking studies and molecular dynamics (MD) simulation of the investigated compounds was performed to verify their binding modes toward EGFR kinase receptor as the possible targets. This analysis aimed to predict the antitumor mechanisms of the synthesized compounds. The binding free energy values of the compounds showed a satisfactory correlation with their cytotoxic activities.https://doi.org/10.1186/s13065-025-01489-zIndenopyrido[2,3-d]pyrimidineCytotoxic activityMolecular dockingMD Simulation |
| spellingShingle | Leila Emami Ladan Baziyar Al-Anood Mohammad Al-Dies Sara Sadeghian Bi Bi Fatemeh Mirjalili Zeinab Faghih Sajad Khorasani Leila Zamani Soghra Khabnadideh Fe3O4@SiO2-SnCl4-promoted synthesis, cytotoxic evaluation, molecular docking, and MD simulation of some indenopyrido[2,3-d]pyrimidine derivatives BMC Chemistry Indenopyrido[2,3-d]pyrimidine Cytotoxic activity Molecular docking MD Simulation |
| title | Fe3O4@SiO2-SnCl4-promoted synthesis, cytotoxic evaluation, molecular docking, and MD simulation of some indenopyrido[2,3-d]pyrimidine derivatives |
| title_full | Fe3O4@SiO2-SnCl4-promoted synthesis, cytotoxic evaluation, molecular docking, and MD simulation of some indenopyrido[2,3-d]pyrimidine derivatives |
| title_fullStr | Fe3O4@SiO2-SnCl4-promoted synthesis, cytotoxic evaluation, molecular docking, and MD simulation of some indenopyrido[2,3-d]pyrimidine derivatives |
| title_full_unstemmed | Fe3O4@SiO2-SnCl4-promoted synthesis, cytotoxic evaluation, molecular docking, and MD simulation of some indenopyrido[2,3-d]pyrimidine derivatives |
| title_short | Fe3O4@SiO2-SnCl4-promoted synthesis, cytotoxic evaluation, molecular docking, and MD simulation of some indenopyrido[2,3-d]pyrimidine derivatives |
| title_sort | fe3o4 sio2 sncl4 promoted synthesis cytotoxic evaluation molecular docking and md simulation of some indenopyrido 2 3 d pyrimidine derivatives |
| topic | Indenopyrido[2,3-d]pyrimidine Cytotoxic activity Molecular docking MD Simulation |
| url | https://doi.org/10.1186/s13065-025-01489-z |
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