Synthesis and assessment of the cytotoxic effect of some of 1,4-dihydropyridine derivatives which contain azole moiety

A number of 1,4-dihydropyridine derivatives (9a–d, 10a–d and 11a–d) were designed and synthesized by the reaction of 1,3,4-oxadiazole-5-thiones and 1,2,4-triazole-5-thiones to 2,6-dibromomethyl-3,5-diethoxycarbonyl-4-(3- -nitrophenyl)-1,4-dihydropyridine. The synthesized compounds were characterized...

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Auteurs principaux:	Ghoorbannejad Saeed, Akbari Dilmaghani Karim, Nikoo Abbas
Format:	article
Langue:	EN
Publié:	Serbian Chemical Society 2021
Sujets:	dimethylformamide 3-nitrobenzaldehyde 1,3,4-oxadiazole 1,2,4-triazole Chemistry QD1-999
Accès en ligne:	https://doaj.org/article/13b23b33566b44d9a1e654d7a0c5063d
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spelling	oai:doaj.org-article:13b23b33566b44d9a1e654d7a0c5063d2021-11-22T11:03:40ZSynthesis and assessment of the cytotoxic effect of some of 1,4-dihydropyridine derivatives which contain azole moiety0352-51391820-742110.2298/JSC200818064Ghttps://doaj.org/article/13b23b33566b44d9a1e654d7a0c5063d2021-01-01T00:00:00Zhttp://www.doiserbia.nb.rs/img/doi/0352-5139/2021/0352-51392100064G.pdfhttps://doaj.org/toc/0352-5139https://doaj.org/toc/1820-7421A number of 1,4-dihydropyridine derivatives (9a–d, 10a–d and 11a–d) were designed and synthesized by the reaction of 1,3,4-oxadiazole-5-thiones and 1,2,4-triazole-5-thiones to 2,6-dibromomethyl-3,5-diethoxycarbonyl-4-(3- -nitrophenyl)-1,4-dihydropyridine. The synthesized compounds were characterized using FT-IR, 1H-NMR, 13C-NMR spectral data, ESI-MS and elemental analysis. The cytotoxicity of the synthesized compounds was evaluated in human breast cancer (MCF-7) cells based on the results of MTT assay. The results indicated that compound diethyl 4-(3-nitrophenyl)-2,6-bis[((5-(3-nitrophenyl)- 1,3,4-oxadiazol-2-yl)thio)methyl]-1,4-dihydro pyridine-3,5-dicarboxylate (9b) with (IC50 = 23±2.32 μM) was the most potent derivative against MCF-7 cells. Based on the results, the use of oxadiazole moiety in the C2 and C6 positions of 1,4-dihydropyridine ring system enhanced the cytotoxic potential of these derivatives. Therefore, some of the oxadiazole-substituted 1,4-DHPs may facilitate further modifications which result in the discovery of potent cytotoxic agents.Ghoorbannejad SaeedAkbari Dilmaghani KarimNikoo AbbasSerbian Chemical Society articledimethylformamide3-nitrobenzaldehyde1,3,4-oxadiazole1,2,4-triazoleChemistryQD1-999ENJournal of the Serbian Chemical Society, Vol 86, Iss 11, Pp 1013-1021 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	dimethylformamide 3-nitrobenzaldehyde 1,3,4-oxadiazole 1,2,4-triazole Chemistry QD1-999
spellingShingle	dimethylformamide 3-nitrobenzaldehyde 1,3,4-oxadiazole 1,2,4-triazole Chemistry QD1-999 Ghoorbannejad Saeed Akbari Dilmaghani Karim Nikoo Abbas Synthesis and assessment of the cytotoxic effect of some of 1,4-dihydropyridine derivatives which contain azole moiety
description	A number of 1,4-dihydropyridine derivatives (9a–d, 10a–d and 11a–d) were designed and synthesized by the reaction of 1,3,4-oxadiazole-5-thiones and 1,2,4-triazole-5-thiones to 2,6-dibromomethyl-3,5-diethoxycarbonyl-4-(3- -nitrophenyl)-1,4-dihydropyridine. The synthesized compounds were characterized using FT-IR, 1H-NMR, 13C-NMR spectral data, ESI-MS and elemental analysis. The cytotoxicity of the synthesized compounds was evaluated in human breast cancer (MCF-7) cells based on the results of MTT assay. The results indicated that compound diethyl 4-(3-nitrophenyl)-2,6-bis[((5-(3-nitrophenyl)- 1,3,4-oxadiazol-2-yl)thio)methyl]-1,4-dihydro pyridine-3,5-dicarboxylate (9b) with (IC50 = 23±2.32 μM) was the most potent derivative against MCF-7 cells. Based on the results, the use of oxadiazole moiety in the C2 and C6 positions of 1,4-dihydropyridine ring system enhanced the cytotoxic potential of these derivatives. Therefore, some of the oxadiazole-substituted 1,4-DHPs may facilitate further modifications which result in the discovery of potent cytotoxic agents.
format	article
author	Ghoorbannejad Saeed Akbari Dilmaghani Karim Nikoo Abbas
author_facet	Ghoorbannejad Saeed Akbari Dilmaghani Karim Nikoo Abbas
author_sort	Ghoorbannejad Saeed
title	Synthesis and assessment of the cytotoxic effect of some of 1,4-dihydropyridine derivatives which contain azole moiety
title_short	Synthesis and assessment of the cytotoxic effect of some of 1,4-dihydropyridine derivatives which contain azole moiety
title_full	Synthesis and assessment of the cytotoxic effect of some of 1,4-dihydropyridine derivatives which contain azole moiety
title_fullStr	Synthesis and assessment of the cytotoxic effect of some of 1,4-dihydropyridine derivatives which contain azole moiety
title_full_unstemmed	Synthesis and assessment of the cytotoxic effect of some of 1,4-dihydropyridine derivatives which contain azole moiety
title_sort	synthesis and assessment of the cytotoxic effect of some of 1,4-dihydropyridine derivatives which contain azole moiety
publisher	Serbian Chemical Society
publishDate	2021
url	https://doaj.org/article/13b23b33566b44d9a1e654d7a0c5063d
work_keys_str_mv	AT ghoorbannejadsaeed synthesisandassessmentofthecytotoxiceffectofsomeof14dihydropyridinederivativeswhichcontainazolemoiety AT akbaridilmaghanikarim synthesisandassessmentofthecytotoxiceffectofsomeof14dihydropyridinederivativeswhichcontainazolemoiety AT nikooabbas synthesisandassessmentofthecytotoxiceffectofsomeof14dihydropyridinederivativeswhichcontainazolemoiety
_version_	1718417718786392064

Synthesis and assessment of the cytotoxic effect of some of 1,4-dihydropyridine derivatives which contain azole moiety

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