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Synthesis, Spectral, Modeling, Docking and Cytotoxicity Studies on 2‐(2‐aminobenzoyl)‐ N ‐ethylhydrazine‐1‐carbothioamide and its divalent metal complexes
Author(s) -
Hosny Nasser Mohammed,
Hussien Mostafa A.,
Motawa Rana,
Belal Arafa,
AbdelRhman Mohamed H.
Publication year - 2020
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.5922
Subject(s) - chemistry , denticity , ligand (biochemistry) , docking (animal) , crystallography , stereochemistry , enol , deprotonation , metal , hydrogen bond , octahedral molecular geometry , photochemistry , molecule , crystal structure , organic chemistry , ion , receptor , catalysis , medicine , biochemistry , nursing
2‐(2‐aminobenzoyl)‐N‐ethylhydrazine‐1‐carbothioamide (H 3 L) and its Cu (II), Co (II), Ni (II) and Zn (II) complexes have been synthesized. The structures of the isolated compounds were suggested based on elemental analyses, spectral analyses (FTIR, 1 H and 13 CNMR, MS, ESR and UV–Visible) and magnetic moments measurements. The free ligand exists in the keto‐thione form, while in the metal complexes; it exists in the enol form and coordinates as mononegative bidentate via deprotonated enolic oxygen and N 2 H nitrogen. Both Co (II) and Ni (II) complexes have an octahedral, while Cu (II) complex has a square planar geometry. The compounds have direct electronic transitions with optical band gap ( E g ) values in the range 3.14–3.40 eV. The ligand and its complexes were optimized using DFT/B3LYP methodology. The ligand optimization results supported the involvement of the carbonyl oxygen, thione sulfur and N 2 H hydrogen atoms in hydrogen bonding formation. Furthermore, the obtained structures of the ligand and its complexes were subjected to molecular docking study to predict interactions cause their cytotoxicity. Finally, the in vitro cytotoxicity activities of the ligand and its complexes were investigated against Hela and WISH cell lines where the Zn (II) complex exhibited higher activity than the other compounds against the two cell lines in accordance with molecular docking suggestion.