Synthesis of New Quinoline based Morpholine-1,2,3-Triazole Hybrids and their Cytotoxicity

Abstract

Regioselective synthesis of a series of 1-aryl 1,2,3-triazoles-4-methoxy methyl-3-quinoline-2-morpholine employing click reaction is presented. Highly selective and efficient copper(I)-catalyzed 1,3-dipolar cycloaddition between 2-morpholinoquinoline-3-methyl propargyl ether and various aryl azides 5a-j yielded the title compounds 6a-j in 71% to 85%. The structure of all the novel 1,2,3-triazoles was characterized by 1H NMR, 13C NMR, IR and mass spectral analysis. The analogues were evaluated for their in vitro anticancer activity against MDA-MB-231 cell line. All the synthesized compounds were proven to have anticancer activity in comparison to reference drug doxorubicin. Especially, chloro and fluoro substituent compounds demonstrated potent activity with IC50 values of 17.20 ± 0.09 µM and 23.56 ± 0.09 µM, which proved their efficacy and could be further studied for the development of novel chemotherapeutics.