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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...

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Autores principales: Irfan, Ali, Faiz, Sadia, Rasul, Azhar, Zafar, Rehman, Zahoor, Ameer Fawad, Kotwica-Mojzych, Katarzyna, Mojzych, Mariusz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
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.
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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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