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Benzoquinoline Derivatives: An Attractive Approach to Newly Small Molecules with Anticancer Activity

This study presents the synthesis, structural characterization, and in vitro evaluation of anticancer activity of some newly benzo[f]quinoline derivatives. The synthesis is facile and efficient, involving two steps: quaternization of nitrogen heterocycle followed by a [3+2] dipolar cycloaddition rea...

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Autores principales: Oniciuc, Liliana, Amăriucăi-Mantu, Dorina, Diaconu, Dumitrela, Mangalagiu, Violeta, Danac, Ramona, Antoci, Vasilichia, Mangalagiu, Ionel I.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10179047/
https://www.ncbi.nlm.nih.gov/pubmed/37175832
http://dx.doi.org/10.3390/ijms24098124
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author Oniciuc, Liliana
Amăriucăi-Mantu, Dorina
Diaconu, Dumitrela
Mangalagiu, Violeta
Danac, Ramona
Antoci, Vasilichia
Mangalagiu, Ionel I.
author_facet Oniciuc, Liliana
Amăriucăi-Mantu, Dorina
Diaconu, Dumitrela
Mangalagiu, Violeta
Danac, Ramona
Antoci, Vasilichia
Mangalagiu, Ionel I.
author_sort Oniciuc, Liliana
collection PubMed
description This study presents the synthesis, structural characterization, and in vitro evaluation of anticancer activity of some newly benzo[f]quinoline derivatives. The synthesis is facile and efficient, involving two steps: quaternization of nitrogen heterocycle followed by a [3+2] dipolar cycloaddition reaction. The synthesized compounds were characterized by FTIR, NMR, and X-ray diffraction on monocrystal in the case of compounds 6c and 7c. An in vitro single-dose anticancer assay of eighteen benzo[f]quinoline compounds, quaternary salts, and cycloadducts, was performed. The results showed that the most active compounds were quaternary salts 3d and 3f with aromatic R substituents. Quaternary salt 3d revealed non-selective activity against all types of cancer cells, while salt 3f exhibited a highly selective activity against leukemia cells. Compound 3d also presented remarkable cytotoxic efficiency against four distinct types of cancer cells—namely, non-small cell lung cancer HOP–92, melanoma LOX IMVI, melanoma SK–MEL–5, and breast cancer MDA–MB–468. Compound 3f was selected for five-dose screening. The study also includes SAR correlations.
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spelling pubmed-101790472023-05-13 Benzoquinoline Derivatives: An Attractive Approach to Newly Small Molecules with Anticancer Activity Oniciuc, Liliana Amăriucăi-Mantu, Dorina Diaconu, Dumitrela Mangalagiu, Violeta Danac, Ramona Antoci, Vasilichia Mangalagiu, Ionel I. Int J Mol Sci Article This study presents the synthesis, structural characterization, and in vitro evaluation of anticancer activity of some newly benzo[f]quinoline derivatives. The synthesis is facile and efficient, involving two steps: quaternization of nitrogen heterocycle followed by a [3+2] dipolar cycloaddition reaction. The synthesized compounds were characterized by FTIR, NMR, and X-ray diffraction on monocrystal in the case of compounds 6c and 7c. An in vitro single-dose anticancer assay of eighteen benzo[f]quinoline compounds, quaternary salts, and cycloadducts, was performed. The results showed that the most active compounds were quaternary salts 3d and 3f with aromatic R substituents. Quaternary salt 3d revealed non-selective activity against all types of cancer cells, while salt 3f exhibited a highly selective activity against leukemia cells. Compound 3d also presented remarkable cytotoxic efficiency against four distinct types of cancer cells—namely, non-small cell lung cancer HOP–92, melanoma LOX IMVI, melanoma SK–MEL–5, and breast cancer MDA–MB–468. Compound 3f was selected for five-dose screening. The study also includes SAR correlations. MDPI 2023-05-01 /pmc/articles/PMC10179047/ /pubmed/37175832 http://dx.doi.org/10.3390/ijms24098124 Text en © 2023 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
Oniciuc, Liliana
Amăriucăi-Mantu, Dorina
Diaconu, Dumitrela
Mangalagiu, Violeta
Danac, Ramona
Antoci, Vasilichia
Mangalagiu, Ionel I.
Benzoquinoline Derivatives: An Attractive Approach to Newly Small Molecules with Anticancer Activity
title Benzoquinoline Derivatives: An Attractive Approach to Newly Small Molecules with Anticancer Activity
title_full Benzoquinoline Derivatives: An Attractive Approach to Newly Small Molecules with Anticancer Activity
title_fullStr Benzoquinoline Derivatives: An Attractive Approach to Newly Small Molecules with Anticancer Activity
title_full_unstemmed Benzoquinoline Derivatives: An Attractive Approach to Newly Small Molecules with Anticancer Activity
title_short Benzoquinoline Derivatives: An Attractive Approach to Newly Small Molecules with Anticancer Activity
title_sort benzoquinoline derivatives: an attractive approach to newly small molecules with anticancer activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10179047/
https://www.ncbi.nlm.nih.gov/pubmed/37175832
http://dx.doi.org/10.3390/ijms24098124
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