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.
keywords
BIOLOGICAL EVALUATION; 1,2,3-TRIAZOLE DERIVATIVES; POTENT; DESIGN; ANTIBACTERIAL; AGENTS
subject category
Chemistry
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
our authors
Djenisa Rocha
Researcheracknowledgements
Thanks are due to University of Aveiro and FCT/MEC for the financial support to the QOPNA research project (FCT UID/QUI/00062/2013) and to the CICECO-Aveiro Institute of Materials (POCI01-0145-FEDER-007679; FCT UID/CTM/50011/2013), financed by national funds and when appropriate co-financed by FEDER under the PT2020 Partnership Agreement, and to the Portuguese NMR Network. We would like also to thank FCT/MEC and the General Directorate for Scientific Research and Technological Development e DGRSDT of Algeria and Agence Thematique de Recherche en Sciences et Technologie ATRST for approving the co-financed bilateral project PT-DZ/0005. We further wish to thank Pr. Farid Messelmi the Dean of Faculty of Exact Sciences and informatics in the University of Djelfa for providing necessary laboratory facilities to carry out the research work smoothly. The biological assays were carried out at iBiMED's cell culture facility which is supported by national funds through FCT project UID/BIM/04501/2019.