Synthesis, Characterization, Cytotoxicity, Molecular Docking, and Modeling of the New Chelating Agent 2‐Benzoyl‐N‐Phenylhydrazine‐1‐Carbothioamide and Its Metal Complexes

ABSTRACT The ligand 2‐benzoyl‐N‐phenylhydrazine‐1‐carbothioamide (H 3 L) and its Zn(II), Cu(II), Co(II), Ni(II) coordination compounds have been synthesized and characterized. Mass spectra (MS), elemental analyses (CHN), infrared (FTIR), UV‐Visible, electron spin resonance (ESR), 1 HNMR& 13 CNMR, Thermo gravimetrical analyses (TGA) and magnetic moments were used to characterize the synthesized compounds. H 3 L exists in the keto‐thione form, while it chelates the metal ions in a keto‐thiol form via thioamide nitrogen and thiol sulfur after substituting the hydrogen. Tetrahedral stereochemistry was proposed for Ni(II) and Co(II) complexes. EPR indicated the formation of a square planar Cu(II) complex. DFT/B3LYP geometry optimization supported the suggested structures. Direct electronic transitions between HOMO and LUMO, with band gap energy (E g ) 4.3 eV were found for H 3 L. The determined Eg values were reduced to 4.16–4.23 eV in case of the metal complexes. The Molecular docking and cytotoxicity activities of H 3 L and its coordination compounds were investigated against colon (HCT‐116) and liver (HePG‐2) cell lines. H 3 L has a strong cytotoxicity against both HePG‐2 (PDB ID: 4fm9) and HCT‐116 (PDB ID: 3ig7) cell lines with IC 50 17.79 ± 1.2 and 13.46 ± 0.9 µg/ml, respectively. The ligand has higher cytotoxicity than its coordination compounds.