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Novel Hybrid Compounds Containing Benzofuroxan and Aminothiazole Scaffolds: Synthesis and Evaluation of Their Anticancer Activity

A series of novel hybrid compounds containing benzofuroxan and 2-aminothiazole moieties are synthesized via aromatic nucleophilic substitution reaction. Possible reaction pathways have been considered quantum-chemically, which allowed us to suggest the most probable products. The quantum chemical re...

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Autores principales: Chugunova, Elena, Micheletti, Gabriele, Telese, Dario, Boga, Carla, Islamov, Daut, Usachev, Konstantin, Burilov, Alexander, Tulesinova, Alena, Voloshina, Alexandra, Lyubina, Anna, Amerhanova, Syumbelya, Gerasimova, Tatiana, Gilfanova, Aisylu, Syakaev, Victor
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8305974/
https://www.ncbi.nlm.nih.gov/pubmed/34299115
http://dx.doi.org/10.3390/ijms22147497
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author Chugunova, Elena
Micheletti, Gabriele
Telese, Dario
Boga, Carla
Islamov, Daut
Usachev, Konstantin
Burilov, Alexander
Tulesinova, Alena
Voloshina, Alexandra
Lyubina, Anna
Amerhanova, Syumbelya
Gerasimova, Tatiana
Gilfanova, Aisylu
Syakaev, Victor
author_facet Chugunova, Elena
Micheletti, Gabriele
Telese, Dario
Boga, Carla
Islamov, Daut
Usachev, Konstantin
Burilov, Alexander
Tulesinova, Alena
Voloshina, Alexandra
Lyubina, Anna
Amerhanova, Syumbelya
Gerasimova, Tatiana
Gilfanova, Aisylu
Syakaev, Victor
author_sort Chugunova, Elena
collection PubMed
description A series of novel hybrid compounds containing benzofuroxan and 2-aminothiazole moieties are synthesized via aromatic nucleophilic substitution reaction. Possible reaction pathways have been considered quantum-chemically, which allowed us to suggest the most probable products. The quantum chemical results have been proved by X-ray data on one compound belonging to the synthesized series. It was shown that the introduction of substituents to both the thiazole and amine moieties of the compounds under study strongly influences their UV/Vis spectra. Initial substances and obtained hybrid compounds have been tested in vitro as anticancer agents. Target compounds showed selectivity towards M-HeLa tumor cell lines and were found to be more active than starting benzofuroxan and aminothiazoles. Furthermore, they are considerably less toxic to normal liver cells compared to Tamoxifen. The mechanism of action of the studied compounds can be associated with the induction of apoptosis, which proceeds along the mitochondrial pathway. Thus, new hybrids of benzofuroxan are promising candidates for further development as anticancer agents.
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spelling pubmed-83059742021-07-25 Novel Hybrid Compounds Containing Benzofuroxan and Aminothiazole Scaffolds: Synthesis and Evaluation of Their Anticancer Activity Chugunova, Elena Micheletti, Gabriele Telese, Dario Boga, Carla Islamov, Daut Usachev, Konstantin Burilov, Alexander Tulesinova, Alena Voloshina, Alexandra Lyubina, Anna Amerhanova, Syumbelya Gerasimova, Tatiana Gilfanova, Aisylu Syakaev, Victor Int J Mol Sci Article A series of novel hybrid compounds containing benzofuroxan and 2-aminothiazole moieties are synthesized via aromatic nucleophilic substitution reaction. Possible reaction pathways have been considered quantum-chemically, which allowed us to suggest the most probable products. The quantum chemical results have been proved by X-ray data on one compound belonging to the synthesized series. It was shown that the introduction of substituents to both the thiazole and amine moieties of the compounds under study strongly influences their UV/Vis spectra. Initial substances and obtained hybrid compounds have been tested in vitro as anticancer agents. Target compounds showed selectivity towards M-HeLa tumor cell lines and were found to be more active than starting benzofuroxan and aminothiazoles. Furthermore, they are considerably less toxic to normal liver cells compared to Tamoxifen. The mechanism of action of the studied compounds can be associated with the induction of apoptosis, which proceeds along the mitochondrial pathway. Thus, new hybrids of benzofuroxan are promising candidates for further development as anticancer agents. MDPI 2021-07-13 /pmc/articles/PMC8305974/ /pubmed/34299115 http://dx.doi.org/10.3390/ijms22147497 Text en © 2021 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
Chugunova, Elena
Micheletti, Gabriele
Telese, Dario
Boga, Carla
Islamov, Daut
Usachev, Konstantin
Burilov, Alexander
Tulesinova, Alena
Voloshina, Alexandra
Lyubina, Anna
Amerhanova, Syumbelya
Gerasimova, Tatiana
Gilfanova, Aisylu
Syakaev, Victor
Novel Hybrid Compounds Containing Benzofuroxan and Aminothiazole Scaffolds: Synthesis and Evaluation of Their Anticancer Activity
title Novel Hybrid Compounds Containing Benzofuroxan and Aminothiazole Scaffolds: Synthesis and Evaluation of Their Anticancer Activity
title_full Novel Hybrid Compounds Containing Benzofuroxan and Aminothiazole Scaffolds: Synthesis and Evaluation of Their Anticancer Activity
title_fullStr Novel Hybrid Compounds Containing Benzofuroxan and Aminothiazole Scaffolds: Synthesis and Evaluation of Their Anticancer Activity
title_full_unstemmed Novel Hybrid Compounds Containing Benzofuroxan and Aminothiazole Scaffolds: Synthesis and Evaluation of Their Anticancer Activity
title_short Novel Hybrid Compounds Containing Benzofuroxan and Aminothiazole Scaffolds: Synthesis and Evaluation of Their Anticancer Activity
title_sort novel hybrid compounds containing benzofuroxan and aminothiazole scaffolds: synthesis and evaluation of their anticancer activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8305974/
https://www.ncbi.nlm.nih.gov/pubmed/34299115
http://dx.doi.org/10.3390/ijms22147497
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