A step-by-step synthesis of triazole-benzimidazole-chalcone hybrids: Anticancer activity in human cells+

• Autor(a) principal: Djemoui, Amar
• Data de Publicação: 2020
• Outros Autores: Naouri, Abdelkader, Ouahrani, Mohammed Ridha, Djemoui, Djamila, Lahcene, Souli, Lahrech, Mokhtar Boualem, Boukenna, Leila, Albuquerque, Hélio M.T., Saher, Liza, Rocha, Djenisa H.A., Monteiro, Fátima Liliana, Helguero, Luísa A., Bachari, Khaldoun, Talhi, Oualid, Silva, Artur M.S.
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
• Texto Completo: http://hdl.handle.net/10773/36702
• topic: 1,2,3-Triazole; Benzimidazole; Chalcones; Click chemistry; Anticancer activity

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.