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Coumaro-chalcones synthesized under solvent-free conditions as potential agents against malaria, leishmania and trypanosomiasis
Leishmaniasis, trypanosomiasis, and malaria are a group of neglected tropical diseases present in tropical regions and they affect large numbers of people in developing countries. A series of thirteen coumaro-chalcones (A1-A13) were synthesized under solvent-free conditions and their in vitro anti-l...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Elsevier
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8851253/ https://www.ncbi.nlm.nih.gov/pubmed/35198789 http://dx.doi.org/10.1016/j.heliyon.2022.e08939 |
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author | Cuellar, José E. Quiñones, Winston Robledo, Sara Gil, Jesús Durango, Diego |
author_facet | Cuellar, José E. Quiñones, Winston Robledo, Sara Gil, Jesús Durango, Diego |
author_sort | Cuellar, José E. |
collection | PubMed |
description | Leishmaniasis, trypanosomiasis, and malaria are a group of neglected tropical diseases present in tropical regions and they affect large numbers of people in developing countries. A series of thirteen coumaro-chalcones (A1-A13) were synthesized under solvent-free conditions and their in vitro anti-leishmanial, anti-plasmodial, anti-trypanosomal and cytotoxic activities were evaluated. One of these coumaro-chalcones, 3-[(2E)-3-(3-ethoxy-4-hydroxyphenyl)prop-2-enoyl]-2H-chromen-2-one (A12), is a new compound. Compounds 3-[(2E)-3-(3-hydroxyphenyl)prop-2-enoyl]-2H-chromen-2-one (A5), 3-[(2E)-3-(3-methoxyphenyl)prop-2-enoyl]-2H-chromen-2-one (A2) and 3-[(2E)-3-phenylprop-2-enoyl]-2H-chromen-2-one (A1) displayed strong inhibition against intracellular amastigotes of Leishmania panamensis with EC(50) of 2.1 ± 0.1, 2.5 ± 0.2 and 3.7 ± 0.5 μM, respectively. In addition, Plasmodium falciparum was moderately inhibited by the coumarin-chalcone hybrids, particularly A12 (EC(50): 15.0 ± 0.5 μM) and 3-[(2E)-3-(1,3-benzodioxol-5-yl)prop-2-enoyl]-2H-chromen-2-one (A13) (EC(50): 15.2 ± 1.1 μM). Remarkably, the coumaro-chalcone A5 (EC(50): 18.7 ± 2.4 μM) exhibited an inhibition of the Trypanosoma cruzi intracellular amastigotes similar to the commercial drug Benznidazole (EC(50): 14.5 ± 0.1 μM). These results support the therapeutic potential of coumaro-chalcone hybrids. |
format | Online Article Text |
id | pubmed-8851253 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Elsevier |
record_format | MEDLINE/PubMed |
spelling | pubmed-88512532022-02-22 Coumaro-chalcones synthesized under solvent-free conditions as potential agents against malaria, leishmania and trypanosomiasis Cuellar, José E. Quiñones, Winston Robledo, Sara Gil, Jesús Durango, Diego Heliyon Research Article Leishmaniasis, trypanosomiasis, and malaria are a group of neglected tropical diseases present in tropical regions and they affect large numbers of people in developing countries. A series of thirteen coumaro-chalcones (A1-A13) were synthesized under solvent-free conditions and their in vitro anti-leishmanial, anti-plasmodial, anti-trypanosomal and cytotoxic activities were evaluated. One of these coumaro-chalcones, 3-[(2E)-3-(3-ethoxy-4-hydroxyphenyl)prop-2-enoyl]-2H-chromen-2-one (A12), is a new compound. Compounds 3-[(2E)-3-(3-hydroxyphenyl)prop-2-enoyl]-2H-chromen-2-one (A5), 3-[(2E)-3-(3-methoxyphenyl)prop-2-enoyl]-2H-chromen-2-one (A2) and 3-[(2E)-3-phenylprop-2-enoyl]-2H-chromen-2-one (A1) displayed strong inhibition against intracellular amastigotes of Leishmania panamensis with EC(50) of 2.1 ± 0.1, 2.5 ± 0.2 and 3.7 ± 0.5 μM, respectively. In addition, Plasmodium falciparum was moderately inhibited by the coumarin-chalcone hybrids, particularly A12 (EC(50): 15.0 ± 0.5 μM) and 3-[(2E)-3-(1,3-benzodioxol-5-yl)prop-2-enoyl]-2H-chromen-2-one (A13) (EC(50): 15.2 ± 1.1 μM). Remarkably, the coumaro-chalcone A5 (EC(50): 18.7 ± 2.4 μM) exhibited an inhibition of the Trypanosoma cruzi intracellular amastigotes similar to the commercial drug Benznidazole (EC(50): 14.5 ± 0.1 μM). These results support the therapeutic potential of coumaro-chalcone hybrids. Elsevier 2022-02-11 /pmc/articles/PMC8851253/ /pubmed/35198789 http://dx.doi.org/10.1016/j.heliyon.2022.e08939 Text en © 2022 The Authors. Published by Elsevier Ltd. https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Research Article Cuellar, José E. Quiñones, Winston Robledo, Sara Gil, Jesús Durango, Diego Coumaro-chalcones synthesized under solvent-free conditions as potential agents against malaria, leishmania and trypanosomiasis |
title | Coumaro-chalcones synthesized under solvent-free conditions as potential agents against malaria, leishmania and trypanosomiasis |
title_full | Coumaro-chalcones synthesized under solvent-free conditions as potential agents against malaria, leishmania and trypanosomiasis |
title_fullStr | Coumaro-chalcones synthesized under solvent-free conditions as potential agents against malaria, leishmania and trypanosomiasis |
title_full_unstemmed | Coumaro-chalcones synthesized under solvent-free conditions as potential agents against malaria, leishmania and trypanosomiasis |
title_short | Coumaro-chalcones synthesized under solvent-free conditions as potential agents against malaria, leishmania and trypanosomiasis |
title_sort | coumaro-chalcones synthesized under solvent-free conditions as potential agents against malaria, leishmania and trypanosomiasis |
topic | Research Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8851253/ https://www.ncbi.nlm.nih.gov/pubmed/35198789 http://dx.doi.org/10.1016/j.heliyon.2022.e08939 |
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