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 prod-ucts. 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 sub-stances 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 Тamoxifen. 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.

Novel hybrid compounds containing benzofuroxan and aminothiazole scaffolds: Synthesis and evaluation of their anticancer activity

Micheletti G.
Secondo
Membro del Collaboration Group
;
Telese D.
Membro del Collaboration Group
;
Boga C.
Membro del Collaboration Group
;
2021

Abstract

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 prod-ucts. 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 sub-stances 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 Тamoxifen. 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.
Chugunova E.; Micheletti G.; Telese D.; Boga C.; Islamov D.; Usachev K.; Burilov A.; Tulesinova A.; Voloshina A.; Lyubina A.; Amerhanova S.; Gerasimova T.; Gilfanova A.; Syakaev V.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/829989
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