Synthesis, antiproliferative activity and DNA/RNA-binding properties of mono- and bis-(1,2,3-triazolyl)-appended benzimidazo[1,2-a]quinoline derivatives

Synthesis, characterisation and biological evaluation of monometallic Re(i) and heterobimetallic Re(i)/Fe(ii) complexes with a 1,2,3-triazolyl pyridine chelating moiety

“…Regarding the synthesis of complex 9 Re , benzimidazo[1,2-a]quinoline core was prepared by a multi-step synthesis reported earlier. 55 The azide intermediate 8 was prepared from 5-chlorobenzimidazo[1,2-a]quinoline-6-carbonitrile (7) by nucleophilic aromatic substitution with sodium azide in acetonitrile (Scheme 2, bottom). The 1,2,3-triazole linker was subsequently formed by the CuAAC reaction of the azide 8 and 2-ethynylpyridine which afforded ligand 9.…”

“…Fluorescein, commonly employed in cellular biology as a tracer, was shown after photoactivation to significantly decrease the viability of human hepatoblastoma HepG2 cells, 57 while benzimidazo[1,2-a]quinoline derivatives showed pronounced antiproliferative activity, particularly on colon cancer (HCT116) cell lines. 55,58 Within the context above, we have designed ferroceneappended tricarbonylrhenium(I) complexes with the pyridyl-1,2,3-triazolyl, dipyridylamine and dipyridylamine-1,2,3-triazolyl chelating moiety (Fig. 2), which coordinates the Re(I) metal centre, with the aim to evaluate their antiproliferative activity.…”

Current Development in the Synthesis of Benzimidazole-Quinoline Hybrid Analogues and Their Biological Applications

“…Macan and co-workers prepared 2-Fluoro-5-(1H-1,2,3-triazol-1-yl)benzo [4,5] imidazo[1,2-a]quinoline-6-carbonitrile derivatives via Huisgen 1,3-dipolar cycloaddition of the azide derivatives and the corresponding alkynes using Cu(OAc)2 as a catalyst (Figure 10). The presence of 3-chloropropyl functional group in compound (XXVI) and 2-hydroxyethyl side-chain in compound (XXVII) exhibited the most pronounced growth-inhibitory effect on colon cancer (HCT116) cells with IC 50 value of 0.5 μM and 0.6 μM, respectively [43]. Pragathi and co-workers have synthesised a series of chalcone incorporated 2-quinoline-benzimidazole-1,2,4-thiadiazoles by aldol condensation (Figure 11).…”

Hybridized 4‐Trifluoromethyl‐(1,2,3‐triazol‐1‐yl)quinoline System: Synthesis, Photophysics, Selective DNA/HSA Bio‐interactions and Molecular Docking

“…Therefore, molecular hybridization strategies based on combining quinoline and 1,2,3‐triazole heterocycles, such as bioactive pharmacophoric frameworks whose combination (fusion or conjugation) of the mentioned rings in a single hybrid molecule demonstrate enormous relevance in drug discovery given their broad coverage of pharmaceutical and therapeutic applications, including anti‐inflammatory and analgesic, [8] antimicrobial, [9,10] antifungal and antibacterial, [11–14] antitubercular, [15–18] antimalarial, [19] and antiviral [20] activities, strongly influence pharmacokinetics, drug targeting, and mechanisms of action [2,21] . Recent studies of compounds containing a conjugation of different types of aza‐heterocycles in the same molecule (e. g., quinoline and 1,2,3‐triazole) have also received considerable attention in therapeutic and anticancer applications [22–25] . The molecular binding studies of these compounds are important tool to understand the interaction mode of these compounds with different biomolecules [22,26] …”