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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...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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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. |
format | Online Article Text |
id | pubmed-10179047 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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