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Exploring the Synergistic Anticancer Potential of Benzofuran–Oxadiazoles and Triazoles: Improved Ultrasound- and Microwave-Assisted Synthesis, Molecular Docking, Hemolytic, Thrombolytic and Anticancer Evaluation of Furan-Based Molecules
Ultrasound- and microwave-assisted green synthetic strategies were applied to furnish benzofuran–oxadiazole 5a–g and benzofuran–triazole 7a–h derivatives in good to excellent yields (60–96%), in comparison with conventional methods (36–80% yield). These synthesized derivatives were screened for hemo...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8838991/ https://www.ncbi.nlm.nih.gov/pubmed/35164286 http://dx.doi.org/10.3390/molecules27031023 |
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author | Irfan, Ali Faiz, Sadia Rasul, Azhar Zafar, Rehman Zahoor, Ameer Fawad Kotwica-Mojzych, Katarzyna Mojzych, Mariusz |
author_facet | Irfan, Ali Faiz, Sadia Rasul, Azhar Zafar, Rehman Zahoor, Ameer Fawad Kotwica-Mojzych, Katarzyna Mojzych, Mariusz |
author_sort | Irfan, Ali |
collection | PubMed |
description | Ultrasound- and microwave-assisted green synthetic strategies were applied to furnish benzofuran–oxadiazole 5a–g and benzofuran–triazole 7a–h derivatives in good to excellent yields (60–96%), in comparison with conventional methods (36–80% yield). These synthesized derivatives were screened for hemolysis, thrombolysis and anticancer therapeutic potential against an A549 lung cancer cell line using an MTT assay. Derivatives 7b (0.1%) and 5e (0.5%) showed the least toxicity against RBCs. Hybrid 7f showed excellent thrombolysis activity (61.4%) when compared against reference ABTS. The highest anticancer activity was displayed by the 5d structural hybridwith cell viability 27.49 ± 1.90 and IC(50) 6.3 ± 0.7 μM values, which were considerably lower than the reference drug crizotinib (IC(50) 8.54 ± 0.84 μM). Conformational analysis revealed the spatial arrangement of compound 5d, which demonstrated its significant potency in comparison with crizotinib; therefore, scaffold 5d would be a promising anticancer agent on the basis of cytotoxicity studies, as well as in silico modeling studies. |
format | Online Article Text |
id | pubmed-8838991 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-88389912022-02-13 Exploring the Synergistic Anticancer Potential of Benzofuran–Oxadiazoles and Triazoles: Improved Ultrasound- and Microwave-Assisted Synthesis, Molecular Docking, Hemolytic, Thrombolytic and Anticancer Evaluation of Furan-Based Molecules Irfan, Ali Faiz, Sadia Rasul, Azhar Zafar, Rehman Zahoor, Ameer Fawad Kotwica-Mojzych, Katarzyna Mojzych, Mariusz Molecules Article Ultrasound- and microwave-assisted green synthetic strategies were applied to furnish benzofuran–oxadiazole 5a–g and benzofuran–triazole 7a–h derivatives in good to excellent yields (60–96%), in comparison with conventional methods (36–80% yield). These synthesized derivatives were screened for hemolysis, thrombolysis and anticancer therapeutic potential against an A549 lung cancer cell line using an MTT assay. Derivatives 7b (0.1%) and 5e (0.5%) showed the least toxicity against RBCs. Hybrid 7f showed excellent thrombolysis activity (61.4%) when compared against reference ABTS. The highest anticancer activity was displayed by the 5d structural hybridwith cell viability 27.49 ± 1.90 and IC(50) 6.3 ± 0.7 μM values, which were considerably lower than the reference drug crizotinib (IC(50) 8.54 ± 0.84 μM). Conformational analysis revealed the spatial arrangement of compound 5d, which demonstrated its significant potency in comparison with crizotinib; therefore, scaffold 5d would be a promising anticancer agent on the basis of cytotoxicity studies, as well as in silico modeling studies. MDPI 2022-02-02 /pmc/articles/PMC8838991/ /pubmed/35164286 http://dx.doi.org/10.3390/molecules27031023 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Irfan, Ali Faiz, Sadia Rasul, Azhar Zafar, Rehman Zahoor, Ameer Fawad Kotwica-Mojzych, Katarzyna Mojzych, Mariusz Exploring the Synergistic Anticancer Potential of Benzofuran–Oxadiazoles and Triazoles: Improved Ultrasound- and Microwave-Assisted Synthesis, Molecular Docking, Hemolytic, Thrombolytic and Anticancer Evaluation of Furan-Based Molecules |
title | Exploring the Synergistic Anticancer Potential of Benzofuran–Oxadiazoles and Triazoles: Improved Ultrasound- and Microwave-Assisted Synthesis, Molecular Docking, Hemolytic, Thrombolytic and Anticancer Evaluation of Furan-Based Molecules |
title_full | Exploring the Synergistic Anticancer Potential of Benzofuran–Oxadiazoles and Triazoles: Improved Ultrasound- and Microwave-Assisted Synthesis, Molecular Docking, Hemolytic, Thrombolytic and Anticancer Evaluation of Furan-Based Molecules |
title_fullStr | Exploring the Synergistic Anticancer Potential of Benzofuran–Oxadiazoles and Triazoles: Improved Ultrasound- and Microwave-Assisted Synthesis, Molecular Docking, Hemolytic, Thrombolytic and Anticancer Evaluation of Furan-Based Molecules |
title_full_unstemmed | Exploring the Synergistic Anticancer Potential of Benzofuran–Oxadiazoles and Triazoles: Improved Ultrasound- and Microwave-Assisted Synthesis, Molecular Docking, Hemolytic, Thrombolytic and Anticancer Evaluation of Furan-Based Molecules |
title_short | Exploring the Synergistic Anticancer Potential of Benzofuran–Oxadiazoles and Triazoles: Improved Ultrasound- and Microwave-Assisted Synthesis, Molecular Docking, Hemolytic, Thrombolytic and Anticancer Evaluation of Furan-Based Molecules |
title_sort | exploring the synergistic anticancer potential of benzofuran–oxadiazoles and triazoles: improved ultrasound- and microwave-assisted synthesis, molecular docking, hemolytic, thrombolytic and anticancer evaluation of furan-based molecules |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8838991/ https://www.ncbi.nlm.nih.gov/pubmed/35164286 http://dx.doi.org/10.3390/molecules27031023 |
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