Design, synthesis and antiproliferative activity studies of 1,2,3-triazole–chalcones

Abstract

A series of 1,2,3-triazole-chalcone hybrids were designed, synthesized and evaluated for their antiproliferative activity against three selected cancer cell lines (SK-N-SH, HepG-2 and MGC-803). Most of the synthesized compounds exhibited moderate to good activity against all the cancer cell lines selected. Particularly, compound 12k showed the most excellent antiproliferative activity with an IC 50 value of 1.53 µM against SK-N-SH cancer cells. The mechanism studies revealed that compound 12k inhibited the proliferation of SK-N-SH cancer cells by inducing apoptosis and arresting the cell cycle at G1 phase.

An Overview of Recent Advances in the Applications of Click Chemistry in the Synthesis of Bioconjugates with Anticancer Activities

“…Fu et al . have reported the synthesis of a series of 1,2,3 ‐ triazole ‐ chalcone molecules by this procedure that corresponding azide intermediates were reacted with compounds 25 in the presence of CuSO 4 .5H 2 O and sodium ascorbate in THF/H 2 O at mild temperature to synthesize compounds 26 .…”

Efficient click reaction towards novel sulfonamide hybrids by molecular hybridization strategy as antiproliferative agents

“…8 On the other hand, two series of 1, 2, 3-triazole derivatives in our group have revealed their anticancer activity: Chalcone-1, 2, 3-triazole-azole 4 showed the potent antiproliferative activity with an IC 50 value of 1.52 μmol against SK-N-SH cancer cells and induced morphological changes; 9 1, 2, 3-Triazole-chalcone 5 (Figure 2) inhibited the proliferation of SK-N-SH cancer cells by inducing apoptosis and arresting the cell cycle at the G1 phase. 10 Molecular hybridization strategy is a new concept in drug design and development based on the combination of pharmacophoric moieties of different bioactive substances to produce a new hybrid compound with improved affinity and efficacy, when compared to the parent drugs. 11 Based on the above interesting findings and our continuous quest to synthesize antitumor agents, [12][13][14][15][16] led us to carry out the molecular hybridization of biologically active sulfonamide and 1, 2, 3-triazole to integrate them in one molecular platform to generate new hybrid architecture with the aim of exploring the impact of such modification on the anticancer agents.…”

Design and synthesis of formononetin-dithiocarbamate hybrids that inhibit growth and migration of PC-3 cells via MAPK/Wnt signaling pathways

“…Molecular hybridization is a useful strategy of rational design of new ligands based on the recognition of pharmacophoric subunits in the molecular structure of two or more known bioactive derivatives [21]. These above interesting findings and our continuous quest to identify more potent anticancer agents, led to the molecular hybridization of formononetin and dithiocarbamate to integrate them in one molecular platform to generate a new hybrid with an excellent antiproliferative activity (Fig.…”