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Facile synthesis and antiproliferative activity of new 3-cyanopyridines
BACKGROUND: Pyridines have been reported to possess various pharmacological activities. RESULTS: Sodium 3-oxo-3-(2-oxo-2H-chromen-3-yl)prop-1-en-1-olate (2) and sodium 3-oxo-3-(3-oxo-3H-benzo[f]chromen-2-yl)prop-1-en-1-olate (7) were prepared and reacted with 2-cyano-N’-(1-aryl(heteryl)ethylidene)ac...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Springer International Publishing
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6935226/ https://www.ncbi.nlm.nih.gov/pubmed/31891163 http://dx.doi.org/10.1186/s13065-019-0652-1 |
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author | Abdel-aziz, Hassan M. Gomha, Sobhi M. El-Sayed, Abdelaziz A. Mabkhot, Yahia Nasser Alsayari, Abdulrhman Muhsinah, Abdullatif Bin |
author_facet | Abdel-aziz, Hassan M. Gomha, Sobhi M. El-Sayed, Abdelaziz A. Mabkhot, Yahia Nasser Alsayari, Abdulrhman Muhsinah, Abdullatif Bin |
author_sort | Abdel-aziz, Hassan M. |
collection | PubMed |
description | BACKGROUND: Pyridines have been reported to possess various pharmacological activities. RESULTS: Sodium 3-oxo-3-(2-oxo-2H-chromen-3-yl)prop-1-en-1-olate (2) and sodium 3-oxo-3-(3-oxo-3H-benzo[f]chromen-2-yl)prop-1-en-1-olate (7) were prepared and reacted with 2-cyano-N’-(1-aryl(heteryl)ethylidene)acetohydrazides 3a–d to produce 2-oxo-1,2-dihydropyridine-3-carbonitrile derivatives 5a–d and 9a–d, respectively, in good yields. Also, 3a–d reacted with sodium (2-oxocyclopentylidene)methanolate (11a) or sodium (2-oxocyclohexylidene) methanolate (11b) to yield 2-oxo-tetrahydro-1H-cyclopenta[b]pyridine-3-carbonitriles 13a–d and 2-oxo-hexahydroquinoline-3-carbonitriles 13e–h, respectively. The mechanisms that account for the formation of the products are discussed. Additionally, the structures of all the newly synthesized products are confirmed, based on elemental analysis and spectral data. Several of the newly synthesized compounds are evaluated for their antitumor activity against HEPG2 and their structure activity relationship (SAR) was studied. CONCLUSIONS: The results revealed that the pyridine derivatives 5c and 5d (IC(50) = 1.46, 7.08 µM, respectively) have promising antitumor activity against liver carcinoma cell line (HEPG2), compared to the reference drug, doxorubicin. [Image: see text] |
format | Online Article Text |
id | pubmed-6935226 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Springer International Publishing |
record_format | MEDLINE/PubMed |
spelling | pubmed-69352262019-12-30 Facile synthesis and antiproliferative activity of new 3-cyanopyridines Abdel-aziz, Hassan M. Gomha, Sobhi M. El-Sayed, Abdelaziz A. Mabkhot, Yahia Nasser Alsayari, Abdulrhman Muhsinah, Abdullatif Bin BMC Chem Research Article BACKGROUND: Pyridines have been reported to possess various pharmacological activities. RESULTS: Sodium 3-oxo-3-(2-oxo-2H-chromen-3-yl)prop-1-en-1-olate (2) and sodium 3-oxo-3-(3-oxo-3H-benzo[f]chromen-2-yl)prop-1-en-1-olate (7) were prepared and reacted with 2-cyano-N’-(1-aryl(heteryl)ethylidene)acetohydrazides 3a–d to produce 2-oxo-1,2-dihydropyridine-3-carbonitrile derivatives 5a–d and 9a–d, respectively, in good yields. Also, 3a–d reacted with sodium (2-oxocyclopentylidene)methanolate (11a) or sodium (2-oxocyclohexylidene) methanolate (11b) to yield 2-oxo-tetrahydro-1H-cyclopenta[b]pyridine-3-carbonitriles 13a–d and 2-oxo-hexahydroquinoline-3-carbonitriles 13e–h, respectively. The mechanisms that account for the formation of the products are discussed. Additionally, the structures of all the newly synthesized products are confirmed, based on elemental analysis and spectral data. Several of the newly synthesized compounds are evaluated for their antitumor activity against HEPG2 and their structure activity relationship (SAR) was studied. CONCLUSIONS: The results revealed that the pyridine derivatives 5c and 5d (IC(50) = 1.46, 7.08 µM, respectively) have promising antitumor activity against liver carcinoma cell line (HEPG2), compared to the reference drug, doxorubicin. [Image: see text] Springer International Publishing 2019-12-28 /pmc/articles/PMC6935226/ /pubmed/31891163 http://dx.doi.org/10.1186/s13065-019-0652-1 Text en © The Author(s) 2019 Open AccessThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated in a credit line to the data. |
spellingShingle | Research Article Abdel-aziz, Hassan M. Gomha, Sobhi M. El-Sayed, Abdelaziz A. Mabkhot, Yahia Nasser Alsayari, Abdulrhman Muhsinah, Abdullatif Bin Facile synthesis and antiproliferative activity of new 3-cyanopyridines |
title | Facile synthesis and antiproliferative activity of new 3-cyanopyridines |
title_full | Facile synthesis and antiproliferative activity of new 3-cyanopyridines |
title_fullStr | Facile synthesis and antiproliferative activity of new 3-cyanopyridines |
title_full_unstemmed | Facile synthesis and antiproliferative activity of new 3-cyanopyridines |
title_short | Facile synthesis and antiproliferative activity of new 3-cyanopyridines |
title_sort | facile synthesis and antiproliferative activity of new 3-cyanopyridines |
topic | Research Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6935226/ https://www.ncbi.nlm.nih.gov/pubmed/31891163 http://dx.doi.org/10.1186/s13065-019-0652-1 |
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