Synthesis of Some N-(1H-Benzo[d]imidazol-2-yl)-2-(4-Arylpiperazin-1-yl) acetamides as Anticancer Agents

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dc.authoridElhaty, Ismail A./0000-0003-4492-2181
dc.contributor.authorSaadeh, Haythem
dc.contributor.authorKaddoura, Raneem
dc.contributor.authorEl-Haty, Ismail
dc.contributor.authorKhasawneh, Mohammad
dc.contributor.authorSamadi, Abdelouahid
dc.contributor.authorSemlali, Abdelhabib
dc.contributor.authorAbutaha, Nael
dc.date.accessioned2024-09-11T19:53:27Z
dc.date.available2024-09-11T19:53:27Z
dc.date.issued2023
dc.departmentİstanbul Gelişim Üniversitesien_US
dc.description.abstractA series of eight N-(1H-benzo[d]imidazol-2-yl)-2-(4-arylpiperazin-1-yl)acetamides was synthesized as potential anticancer agents. Reacting 2-aminobenzimidazole (1) with 2-chloroacetyl chloride in the presence of the base gave N-(1H-benzo[d]imidazol-2-yl)-2-chloroacetamide (2) which then reacted with substituted piperazines 3a-h to give the targeted compounds 4a-h. The cytotoxic activity of lung (A549) and liver (HepG2) human cancer cells was assessed using the MTT assay. The results demonstrated that IC50 values of 4b, 4c, 4g, and 4h were 4.8 mu M, 13.3 mu M, 5.1 mu M, and 11.5 mu M on HepG2 cells, respectively. Similarly, the IC50 values of 4b, 4c, 4g, and 4h were 56.9 mu M, 46.6 mu M, 53.2 mu M, and 59.4 mu M on A549 cells after 48 h treatment, respectively. The compounds showed higher anticancer activity against HepG2 cells than A549 cells. Compound 4b and 4g mediated cytotoxicity in HepG2 cells by inducing apoptotic cell death, as revealed by fluorescence microscopy. An in silico study was carried out to study the interactions with the active binding site of different receptors. Vascular endothelial growth factor receptor 2 crystal structures (PDB ID; 4ASD) indicated a strong binding mode of 4g compound (Delta G=-10.28 kcal/mol), corresponding with their cytotoxic activities.en_US
dc.description.sponsorshipKing Saud University, Riyadh, Saudi Arabia [RSPD2024R757]en_US
dc.description.sponsorshipThe authors of this study extend their appreciation to Researchers Supporting Project (RSPD2024R757), King Saud University, Riyadh, Saudi Arabia.en_US
dc.identifier.doi10.59467/IJHC.2023.33.499
dc.identifier.endpage507en_US
dc.identifier.issn0971-1627
dc.identifier.issn2456-4311
dc.identifier.issue4en_US
dc.identifier.scopus2-s2.0-85185271412en_US
dc.identifier.startpage499en_US
dc.identifier.urihttps://doi.org/10.59467/IJHC.2023.33.499
dc.identifier.urihttps://hdl.handle.net/11363/8139
dc.identifier.volume33en_US
dc.identifier.wosWOS:001195331600015en_US
dc.identifier.wosqualityQ4en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.language.isoenen_US
dc.publisherConnect Journalsen_US
dc.relation.ispartofIndian Journal of Heterocyclic Chemistryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.snmz20240903_Gen_US
dc.subjectAnticancer activityen_US
dc.subjectApoptosisen_US
dc.subjectBenzimidazoleen_US
dc.subjectPiperazinesen_US
dc.titleSynthesis of Some N-(1H-Benzo[d]imidazol-2-yl)-2-(4-Arylpiperazin-1-yl) acetamides as Anticancer Agentsen_US
dc.typeArticleen_US

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