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Eco-friendly synthesis of new olanzapine derivatives and evaluation of their anticancer potential

New derivatives of the known antipsychotic drug olanzapine have been obtained as potential compounds with anticancer activity in two metabolically different breast cancer cell lines: MCF-7 and triple negative MDA-MB-231. The compounds were obtained under phase transfer catalysis (PTC) in the presenc...

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Autores principales: Drabczyk, Anna K., Kułaga, Damian, Zaręba, Przemysław, Tylińska, Wiktoria, Bachowski, Wojciech, Archała, Aneta, Wnorowski, Artur, Tzani, Andromachi, Detsi, Anastasia, Jaśkowska, Jolanta
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10331126/
https://www.ncbi.nlm.nih.gov/pubmed/37435368
http://dx.doi.org/10.1039/d3ra03926a
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author Drabczyk, Anna K.
Kułaga, Damian
Zaręba, Przemysław
Tylińska, Wiktoria
Bachowski, Wojciech
Archała, Aneta
Wnorowski, Artur
Tzani, Andromachi
Detsi, Anastasia
Jaśkowska, Jolanta
author_facet Drabczyk, Anna K.
Kułaga, Damian
Zaręba, Przemysław
Tylińska, Wiktoria
Bachowski, Wojciech
Archała, Aneta
Wnorowski, Artur
Tzani, Andromachi
Detsi, Anastasia
Jaśkowska, Jolanta
author_sort Drabczyk, Anna K.
collection PubMed
description New derivatives of the known antipsychotic drug olanzapine have been obtained as potential compounds with anticancer activity in two metabolically different breast cancer cell lines: MCF-7 and triple negative MDA-MB-231. The compounds were obtained under phase transfer catalysis (PTC) in the presence of microwave irradiation (MW) or ultrasound (“)))”), evaluating the effect of solvents such as dimethylformamide, water, or choline chloride/urea (natural deep eutectic solvent, NaDES). In the best option, the compounds were obtained within 2 minutes with a yield of 57–86% in MW. Two of the obtained compounds which have a naphthalimide moiety and a pentyl (7) or hexyl chain (8) show pronounced cytotoxicity. Interestingly, neither olanzapine nor desmethylolanzapine (DOLA), which was one of the substrates for the synthesis reaction, showed any significant activity in the study.
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spelling pubmed-103311262023-07-11 Eco-friendly synthesis of new olanzapine derivatives and evaluation of their anticancer potential Drabczyk, Anna K. Kułaga, Damian Zaręba, Przemysław Tylińska, Wiktoria Bachowski, Wojciech Archała, Aneta Wnorowski, Artur Tzani, Andromachi Detsi, Anastasia Jaśkowska, Jolanta RSC Adv Chemistry New derivatives of the known antipsychotic drug olanzapine have been obtained as potential compounds with anticancer activity in two metabolically different breast cancer cell lines: MCF-7 and triple negative MDA-MB-231. The compounds were obtained under phase transfer catalysis (PTC) in the presence of microwave irradiation (MW) or ultrasound (“)))”), evaluating the effect of solvents such as dimethylformamide, water, or choline chloride/urea (natural deep eutectic solvent, NaDES). In the best option, the compounds were obtained within 2 minutes with a yield of 57–86% in MW. Two of the obtained compounds which have a naphthalimide moiety and a pentyl (7) or hexyl chain (8) show pronounced cytotoxicity. Interestingly, neither olanzapine nor desmethylolanzapine (DOLA), which was one of the substrates for the synthesis reaction, showed any significant activity in the study. The Royal Society of Chemistry 2023-07-10 /pmc/articles/PMC10331126/ /pubmed/37435368 http://dx.doi.org/10.1039/d3ra03926a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Drabczyk, Anna K.
Kułaga, Damian
Zaręba, Przemysław
Tylińska, Wiktoria
Bachowski, Wojciech
Archała, Aneta
Wnorowski, Artur
Tzani, Andromachi
Detsi, Anastasia
Jaśkowska, Jolanta
Eco-friendly synthesis of new olanzapine derivatives and evaluation of their anticancer potential
title Eco-friendly synthesis of new olanzapine derivatives and evaluation of their anticancer potential
title_full Eco-friendly synthesis of new olanzapine derivatives and evaluation of their anticancer potential
title_fullStr Eco-friendly synthesis of new olanzapine derivatives and evaluation of their anticancer potential
title_full_unstemmed Eco-friendly synthesis of new olanzapine derivatives and evaluation of their anticancer potential
title_short Eco-friendly synthesis of new olanzapine derivatives and evaluation of their anticancer potential
title_sort eco-friendly synthesis of new olanzapine derivatives and evaluation of their anticancer potential
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10331126/
https://www.ncbi.nlm.nih.gov/pubmed/37435368
http://dx.doi.org/10.1039/d3ra03926a
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