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Synthesis and biological activity of novel coumarin and quinoline hybrids bridged by 1,2,3-triazole ring

The field of medicinal chemistry has numerous examples of heterocyclic molecules having a wide range of use and properties. In continuous efforts to find more potent and efficient molecules, development of molecular hybrids using combinations of moieties that are proven to be biologically active is an emerging trend in drug discovery [1]. Coumarin and quinoline are two heterocyclic scaffolds that have a wide range of biological activity and play an essential role in many pharmaceuticals. Their use in new hybrids using 1, 2, 3-triazole linkages has recently been reported in several studies [2, 3], In this work, we present novel, potentially biologically active, hybrids of coumarin and quinoline bridged with 1, 2, 3-triazole linkage that were synthesized using azidoquinoline and terminal alkyne bearing coumarin and quinoline precursors. Terminal alkyne coumarin and quinoline precursors that have an ether linkage were prepared from hydroxycoumarin derivatives via nucleophilic substitution with propargyl bromide. The 4-ethynylcoumarin for the synthesis of 1-4 was prepared from hydroxycoumarin derivatives by Sonogashira reaction of a previously synthesized coumarin triflate and trimethylsilylacetylene followed by deprotection using potassium carbonate. Coumarin and quinoline hybrids bridged with 1, 2, 3-triazole (1-21) were synthesized using a copper catalyzed Huisgen-1, 3-dipolarcycloaddition and evaluated against Gram-positive and Gram-negative bacterial strains. [1] G. Bérubé, Expert Opinion on Drug Discovery 11 (2016) 281. [2] R. Reddyrajula et al., Chemistry Select 4(2019) 2685. [3] Kavita Bhagat et. al., ACS Omega 4 (2019) 8720.

quinoline, coumarin, 1, 2, 3-triazole, molecular hybrids

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