A step-by-step synthesis of triazole-benzimidazole-chalcone hybrids: Anticancer activity in human cells(+)
authors Djemoui, A; Naouri, A; Ouahrani, MR; Djemoui, D; Lahcene, S; Lahrech, MB; Boukenna, L; Albuquerque, HMT; Saher, L; Rocha, DHA; Monteiro, FL; Helguero, LA; Bachari, K; Talhi, O; Silva, AMS
nationality International
journal JOURNAL OF MOLECULAR STRUCTURE
author keywords 1,2,3-Triazole; Benzimidazole; Chalcones; Click chemistry; Anticancer activity
keywords BIOLOGICAL EVALUATION; 1,2,3-TRIAZOLE DERIVATIVES; POTENT; DESIGN; ANTIBACTERIAL; AGENTS
abstract Novel series of triazole-benzimidazole-chalcone hybrid compounds have been synthesized via click chemistry, between different azide derivatives and substituted benzimidazole terminal alkynes bearing a chalcone moiety. The starting alkynes are prepared via base-catalysed nitrogen alkylation of pre-synthetized benzimidazole-chalcone substrates. All the intermediates as well as the final products are fully characterized by 1D and 2D NMR and mass spectrometry techniques. HMBC correlations permits the identification of a unique 1,4-disubstitued triazole-benzimidazole-chalcone isomer. Evaluation of the anti-proliferative potential in breast and prostate cancer cell lines showed that the presence of chloro substituents at the chalcone ring of the triazole-benzimidazole-chalcone skeleton enhanced the cytotoxic effects. The benzyl group linked to the 1,2,3-triazole moiety provides more antiproliferative potential. (C) 2019 Elsevier B.V. All rights reserved.
publisher ELSEVIER
issn 0022-2860
year published 2020
volume 1204
digital object identifier (doi) 10.1016/j.molstruc.2019.127487
web of science category Chemistry, Physical
subject category Chemistry
unique article identifier WOS:000508216300008
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journal impact factor 2.463
5 year journal impact factor 2.121
category normalized journal impact factor percentile 42.453
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