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Synthesis, Antitumor Evaluation and Molecular Docking of New Morpholine Based Heterocycles
A series of new morpholinylchalcones was prepared and then used as building blocks for constructing a series of 7-morpholino-2-thioxo-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-ones via their reaction with 6-aminothiouracil. The latter thiones reacted with the appropriate hydrazonoyl chloride to give t...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6152077/ https://www.ncbi.nlm.nih.gov/pubmed/28726760 http://dx.doi.org/10.3390/molecules22071211 |
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author | Muhammad, Zeinab A. Edrees, Mastoura M. Faty, Rasha A. M. Gomha, Sobhi M. Alterary, Seham S. Mabkhot, Yahia N. |
author_facet | Muhammad, Zeinab A. Edrees, Mastoura M. Faty, Rasha A. M. Gomha, Sobhi M. Alterary, Seham S. Mabkhot, Yahia N. |
author_sort | Muhammad, Zeinab A. |
collection | PubMed |
description | A series of new morpholinylchalcones was prepared and then used as building blocks for constructing a series of 7-morpholino-2-thioxo-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-ones via their reaction with 6-aminothiouracil. The latter thiones reacted with the appropriate hydrazonoyl chloride to give the corresponding pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-ones. The assigned structures for all the newly synthesized compounds were confirmed on the basis of elemental analyses and spectral data and the mechanisms of their formation were also discussed. Most of the synthesized compounds were tested for in vitro activity against human lung cancer (A-549) and human hepatocellular carcinoma (HepG-2) cell lines compared with the employed standard antitumor drug (cisplatin) and the results revealed that compounds 8, 4e and 7b have promising activities against the A-549 cell line (IC(50) values of 2.78 ± 0.86 μg/mL, 5.37 ± 0.95 μg/mL and 5.70 ± 0.91 μg/mL, respectively) while compound 7b has promising activity against the HepG-2 cell lines (IC(50) = 3.54 ± 1.11 μg/mL). Moreover, computational studies using MOE 2014.09 software supported the biological activity results. |
format | Online Article Text |
id | pubmed-6152077 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-61520772018-11-13 Synthesis, Antitumor Evaluation and Molecular Docking of New Morpholine Based Heterocycles Muhammad, Zeinab A. Edrees, Mastoura M. Faty, Rasha A. M. Gomha, Sobhi M. Alterary, Seham S. Mabkhot, Yahia N. Molecules Article A series of new morpholinylchalcones was prepared and then used as building blocks for constructing a series of 7-morpholino-2-thioxo-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-ones via their reaction with 6-aminothiouracil. The latter thiones reacted with the appropriate hydrazonoyl chloride to give the corresponding pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-ones. The assigned structures for all the newly synthesized compounds were confirmed on the basis of elemental analyses and spectral data and the mechanisms of their formation were also discussed. Most of the synthesized compounds were tested for in vitro activity against human lung cancer (A-549) and human hepatocellular carcinoma (HepG-2) cell lines compared with the employed standard antitumor drug (cisplatin) and the results revealed that compounds 8, 4e and 7b have promising activities against the A-549 cell line (IC(50) values of 2.78 ± 0.86 μg/mL, 5.37 ± 0.95 μg/mL and 5.70 ± 0.91 μg/mL, respectively) while compound 7b has promising activity against the HepG-2 cell lines (IC(50) = 3.54 ± 1.11 μg/mL). Moreover, computational studies using MOE 2014.09 software supported the biological activity results. MDPI 2017-07-20 /pmc/articles/PMC6152077/ /pubmed/28726760 http://dx.doi.org/10.3390/molecules22071211 Text en © 2017 by the authors. 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 (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Muhammad, Zeinab A. Edrees, Mastoura M. Faty, Rasha A. M. Gomha, Sobhi M. Alterary, Seham S. Mabkhot, Yahia N. Synthesis, Antitumor Evaluation and Molecular Docking of New Morpholine Based Heterocycles |
title | Synthesis, Antitumor Evaluation and Molecular Docking of New Morpholine Based Heterocycles |
title_full | Synthesis, Antitumor Evaluation and Molecular Docking of New Morpholine Based Heterocycles |
title_fullStr | Synthesis, Antitumor Evaluation and Molecular Docking of New Morpholine Based Heterocycles |
title_full_unstemmed | Synthesis, Antitumor Evaluation and Molecular Docking of New Morpholine Based Heterocycles |
title_short | Synthesis, Antitumor Evaluation and Molecular Docking of New Morpholine Based Heterocycles |
title_sort | synthesis, antitumor evaluation and molecular docking of new morpholine based heterocycles |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6152077/ https://www.ncbi.nlm.nih.gov/pubmed/28726760 http://dx.doi.org/10.3390/molecules22071211 |
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