A step-by-step synthesis of triazole-benzimidazole-chalcone hybrids: Anticancer activity in human cells+
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.
- Publication:
-
Journal of Molecular Structure
- Pub Date:
- March 2020
- DOI:
- 10.1016/j.molstruc.2019.127487
- Bibcode:
- 2020JMoSt120427487D
- Keywords:
-
- 1;
- 2;
- 3-Triazole;
- Benzimidazole;
- Chalcones;
- Click chemistry;
- Anticancer activity