Synthesis and Cytotoxicity of Thieno[2,3-b]Pyridine Derivatives Toward Sensitive and Multidrug-Resistant Leukemia Cells
A new series of substituted ethyl 7-cyclopropyl-2-(2-aryloxo)-3-nitro-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylates 3a–e were prepared by utilizing ethyl 2-chloro-7-cyclopropyl-3-nitro-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylate (1) and replacing of the 2-chlorine with anions obtain...
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Slovenian Chemical Society
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doaj-9564cf5bcf2649a4826a48ab1c565e3a2021-08-25T11:23:40ZengSlovenian Chemical SocietyActa Chimica Slovenica1318-02071580-31552021-06-0168245846510.17344/acsi.2020.6609951Synthesis and Cytotoxicity of Thieno[2,3-b]Pyridine Derivatives Toward Sensitive and Multidrug-Resistant Leukemia CellsSalah A. Al-TrawnehAmer H. TarawnehAnastassiya V. GadetskayaEan-Jeong SeoMohammad R. Al-Ta’aniSamir A. Al-TaweelMustafa M. El-AbadelahA new series of substituted ethyl 7-cyclopropyl-2-(2-aryloxo)-3-nitro-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylates 3a–e were prepared by utilizing ethyl 2-chloro-7-cyclopropyl-3-nitro-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylate (1) and replacing of the 2-chlorine with anions obtained from phenol (2a), salicylaldehyde derivatives 2b–d or thiophenol (2e), leading to the respective ethyl 7-cyclopropyl-2-(2-aryloxo)-3-nitro-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylates 3a–e. The new compounds were evaluated for their in vitro cytotoxicity towards sensitive CCRF-CEM and multidrug-resistant CEM/ADR5000 leukemia cells. The screening revealed that compounds 3a, 3b, and 3e inhibited the growth of both cell lines. Compound 3b, with a phenol moiety, exhibited the highest growth inhibitory activity against CEM/ADR5000 and CCRF-CEM cells with IC50 values 4.486 ± 0.286 and 2.580 ± 0.550 µM, respectively. Collectively, the presented results demonstrate that the synthesized thieno[2,3-b]pyridines warrant further exploration for potential use as anti-cancer agents.https://journals.matheo.si/index.php/ACSi/article/view/6609thieno[2,3-b]pyridinemultidrug resistancecytotoxicity. |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Salah A. Al-Trawneh Amer H. Tarawneh Anastassiya V. Gadetskaya Ean-Jeong Seo Mohammad R. Al-Ta’ani Samir A. Al-Taweel Mustafa M. El-Abadelah |
spellingShingle |
Salah A. Al-Trawneh Amer H. Tarawneh Anastassiya V. Gadetskaya Ean-Jeong Seo Mohammad R. Al-Ta’ani Samir A. Al-Taweel Mustafa M. El-Abadelah Synthesis and Cytotoxicity of Thieno[2,3-b]Pyridine Derivatives Toward Sensitive and Multidrug-Resistant Leukemia Cells Acta Chimica Slovenica thieno[2,3-b]pyridine multidrug resistance cytotoxicity. |
author_facet |
Salah A. Al-Trawneh Amer H. Tarawneh Anastassiya V. Gadetskaya Ean-Jeong Seo Mohammad R. Al-Ta’ani Samir A. Al-Taweel Mustafa M. El-Abadelah |
author_sort |
Salah A. Al-Trawneh |
title |
Synthesis and Cytotoxicity of Thieno[2,3-b]Pyridine Derivatives Toward Sensitive and Multidrug-Resistant Leukemia Cells |
title_short |
Synthesis and Cytotoxicity of Thieno[2,3-b]Pyridine Derivatives Toward Sensitive and Multidrug-Resistant Leukemia Cells |
title_full |
Synthesis and Cytotoxicity of Thieno[2,3-b]Pyridine Derivatives Toward Sensitive and Multidrug-Resistant Leukemia Cells |
title_fullStr |
Synthesis and Cytotoxicity of Thieno[2,3-b]Pyridine Derivatives Toward Sensitive and Multidrug-Resistant Leukemia Cells |
title_full_unstemmed |
Synthesis and Cytotoxicity of Thieno[2,3-b]Pyridine Derivatives Toward Sensitive and Multidrug-Resistant Leukemia Cells |
title_sort |
synthesis and cytotoxicity of thieno[2,3-b]pyridine derivatives toward sensitive and multidrug-resistant leukemia cells |
publisher |
Slovenian Chemical Society |
series |
Acta Chimica Slovenica |
issn |
1318-0207 1580-3155 |
publishDate |
2021-06-01 |
description |
A new series of substituted ethyl 7-cyclopropyl-2-(2-aryloxo)-3-nitro-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylates 3a–e were prepared by utilizing ethyl 2-chloro-7-cyclopropyl-3-nitro-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylate (1) and replacing of the 2-chlorine with anions obtained from phenol (2a), salicylaldehyde derivatives 2b–d or thiophenol (2e), leading to the respective ethyl 7-cyclopropyl-2-(2-aryloxo)-3-nitro-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylates 3a–e. The new compounds were evaluated for their in vitro cytotoxicity towards sensitive CCRF-CEM and multidrug-resistant CEM/ADR5000 leukemia cells. The screening revealed that compounds 3a, 3b, and 3e inhibited the growth of both cell lines. Compound 3b, with a phenol moiety, exhibited the highest growth inhibitory activity against CEM/ADR5000 and CCRF-CEM cells with IC50 values 4.486 ± 0.286 and 2.580 ± 0.550 µM, respectively. Collectively, the presented results demonstrate that the synthesized thieno[2,3-b]pyridines warrant further exploration for potential use as anti-cancer agents. |
topic |
thieno[2,3-b]pyridine multidrug resistance cytotoxicity. |
url |
https://journals.matheo.si/index.php/ACSi/article/view/6609 |
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