Microwave and conventional synthesis of ester based dicationic pyridinium ionic liquids carrying hydrazone linkage: DNA binding, anticancer and docking studies

Novel task dicationic ionic liquids (Ts-DilLs) 6-29 were designed and synthesized, under both conventional and microwave conditions; through molecular hybridization of the appropriate bispyridines having a hydrazone linkage as spacer with some alkyl functionalized esters forming the counter cations. Beside the synthesized halogenated DilLs 6-11, fluorinated metal anions were introduced via metathesis reaction in order to create new dipyridinium ionic liquid-hydrazone hybrids 12-29. All newly synthesized DilLs were fully characterized using different spectroscopic tools such as H-1, C-13, F-19, P-31, B-11 NMR and Mass experiment. The DNA binding, anticancer and docking studies of the synthesized ionic liquids were also carried out. The DNA binding constants ranged from 4.5 x 10(4) to 7.2 x 10(4) M-1, indicating good DNA binding tendencies. The most active ionic liquids were 28 and 29 with 99.99 and 99.86% anticancer activities, respectively. The docking studies indicated DNA binding in the outer grooves of DNA. The reported ionic liquids may be used as future anticancer drugs. (C) 2020 Elsevier B.V. All rights reserved.