Synthesis of novel thiourea-/urea-benzimidazole derivatives as anticancer agents

A new series of urea and thiourea derivatives containing benzimidazole group as potential anticancer agents have been designed and synthesized. The structures of the synthesized compounds were characterized and confirmed by spectroscopic techniques such as 1H NMR, 13C NMR, and mass spectrometry. In...

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Autores principales:	Siddig Lamia A., Khasawneh Mohammad A., Samadi Abdelouahid, Saadeh Haythem, Abutaha Nael, Wadaan Mohammad Ahmed
Formato:	article
Lenguaje:	EN
Publicado:	De Gruyter 2021
Materias:	benzimidazole urea thiourea piperazine anticancer activity apoptosis Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/91eb361b49c6469a81c39ce4d1ab69af
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spelling	oai:doaj.org-article:91eb361b49c6469a81c39ce4d1ab69af2021-12-05T14:10:44ZSynthesis of novel thiourea-/urea-benzimidazole derivatives as anticancer agents2391-542010.1515/chem-2021-0093https://doaj.org/article/91eb361b49c6469a81c39ce4d1ab69af2021-10-01T00:00:00Zhttps://doi.org/10.1515/chem-2021-0093https://doaj.org/toc/2391-5420A new series of urea and thiourea derivatives containing benzimidazole group as potential anticancer agents have been designed and synthesized. The structures of the synthesized compounds were characterized and confirmed by spectroscopic techniques such as 1H NMR, 13C NMR, and mass spectrometry. In vitro anticancer assay against two breast cancer (BC) cell lines, MDA-MB-231ER(−)/PR(−) and MCF-7ER(+)/PR(+), revealed that the cytotoxicity of 1-(2-(1H-benzo[d]imidazol-2-ylamino)ethyl)-3-p-tolylthiourea (7b) and 4-(1H-benzo[d]imidazol-2-yl)-N-(3-chlorophenyl)piperazine-1-carboxamide (5d) were higher in MCF-7 with IC50 values of 25.8 and 48.3 µM, respectively, as compared with MDA-MB-231 cells. Furthermore, 7b and 5d were assessed for their apoptotic potential using 4′,6-diamidino-2-phenylindole, acridine orange/ethidium bromide staining, and Caspase-3/7. After incubation with MCF-7, the compounds 7b and 5d induced apoptosis through caspase-3/7 activation. In conclusion, the compounds 7b and 5d are potential candidates for inducing apoptosis in different genotypic BC cell lines.Siddig Lamia A.Khasawneh Mohammad A.Samadi AbdelouahidSaadeh HaythemAbutaha NaelWadaan Mohammad AhmedDe Gruyterarticlebenzimidazoleureathioureapiperazineanticancer activityapoptosisChemistryQD1-999ENOpen Chemistry, Vol 19, Iss 1, Pp 1062-1073 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	benzimidazole urea thiourea piperazine anticancer activity apoptosis Chemistry QD1-999
spellingShingle	benzimidazole urea thiourea piperazine anticancer activity apoptosis Chemistry QD1-999 Siddig Lamia A. Khasawneh Mohammad A. Samadi Abdelouahid Saadeh Haythem Abutaha Nael Wadaan Mohammad Ahmed Synthesis of novel thiourea-/urea-benzimidazole derivatives as anticancer agents
description	A new series of urea and thiourea derivatives containing benzimidazole group as potential anticancer agents have been designed and synthesized. The structures of the synthesized compounds were characterized and confirmed by spectroscopic techniques such as 1H NMR, 13C NMR, and mass spectrometry. In vitro anticancer assay against two breast cancer (BC) cell lines, MDA-MB-231ER(−)/PR(−) and MCF-7ER(+)/PR(+), revealed that the cytotoxicity of 1-(2-(1H-benzo[d]imidazol-2-ylamino)ethyl)-3-p-tolylthiourea (7b) and 4-(1H-benzo[d]imidazol-2-yl)-N-(3-chlorophenyl)piperazine-1-carboxamide (5d) were higher in MCF-7 with IC50 values of 25.8 and 48.3 µM, respectively, as compared with MDA-MB-231 cells. Furthermore, 7b and 5d were assessed for their apoptotic potential using 4′,6-diamidino-2-phenylindole, acridine orange/ethidium bromide staining, and Caspase-3/7. After incubation with MCF-7, the compounds 7b and 5d induced apoptosis through caspase-3/7 activation. In conclusion, the compounds 7b and 5d are potential candidates for inducing apoptosis in different genotypic BC cell lines.
format	article
author	Siddig Lamia A. Khasawneh Mohammad A. Samadi Abdelouahid Saadeh Haythem Abutaha Nael Wadaan Mohammad Ahmed
author_facet	Siddig Lamia A. Khasawneh Mohammad A. Samadi Abdelouahid Saadeh Haythem Abutaha Nael Wadaan Mohammad Ahmed
author_sort	Siddig Lamia A.
title	Synthesis of novel thiourea-/urea-benzimidazole derivatives as anticancer agents
title_short	Synthesis of novel thiourea-/urea-benzimidazole derivatives as anticancer agents
title_full	Synthesis of novel thiourea-/urea-benzimidazole derivatives as anticancer agents
title_fullStr	Synthesis of novel thiourea-/urea-benzimidazole derivatives as anticancer agents
title_full_unstemmed	Synthesis of novel thiourea-/urea-benzimidazole derivatives as anticancer agents
title_sort	synthesis of novel thiourea-/urea-benzimidazole derivatives as anticancer agents
publisher	De Gruyter
publishDate	2021
url	https://doaj.org/article/91eb361b49c6469a81c39ce4d1ab69af
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Synthesis of novel thiourea-/urea-benzimidazole derivatives as anticancer agents

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