Abstract
Cyanoacetic acid{1-[4-(3,4-dihydro-2H-quinoline-1-sulfonyl)phenyl]ethylidene}hydrazide Schiff base ligand (H2L) has been synthesized by using 1-[4-(3,4-dihydro-2H-quinoline-1-sulfonyl)phenyl]ethanone (QSE) and cyanoacetohydrazide. The H2L ligand was reacted with monodentate Fe(III), Cu(II), Co(II), Ni(II), and Ag(I) metal ions to produce complexes. The H2L ligand and its metal complexes were characterized via elemental analysis, spectral data (FTIR, UV-visible, H-1 NMR, mass), molar conductance, magnetic moment, TGA, and ESR measurements. The novel prepared (H2L) ligand behaves as monobasic and coordinates to the metal ion in 1:1 stoichiometry via the azomethine nitrogen and enolic oxygen atom. The in vitro antimicrobial activities of ligand and their complexes were tested. Complex 1 showed good activity against Klebsiella pneumoniae as Gram-negative bacteria. Compound 2 showed a highly activity against Mycobacterium tuberculosis. In addition, in vitro cytotoxic activities of all the synthesized compounds were evaluated on MCF-7, HTC-116, and HEPG-2 cell lines. Complex 4 exhibited a significant inhibition against MCF-7 and HTC-116 cell lines, H2L exhibited a significant inhibition against HEPG-2 cell line, and complex 1 exhibited a significant inhibition against MCF-7, HTC-116, and HEPG-2 cell lines compared to MTX as a reference drug. Docking studies involving MOE (Molecular Operating Environment) were carried out to find the potential binding affinities between the ligand and the DHFR enzyme. Complex 2 showed more interaction with DHFR, which leads to inhibition of this enzyme.