Synthesis, characterization, biological screening and molecular docking of Zn(II) and Cu(II) complexes of 3,5‐dichlorosalicylaldehyde‐N⁴‐cyclohexylthiosemicarbazone

Abstract

A 3,5‐dichlorosalicylaldehyde‐N4‐cyclohexylthiosemicarbazone (C14H16Cl2N3OS) and its complexes [Zn(dsct)(phen)]·DMF (1), [Zn(dsct)(bipy)]·DMF (2), [Cu(dsct)(bipy)]·DMF (3) (phen = 1,10‐phenathroline, bipy = 2,2’bipyridine) were synthesized and characterized by CHN analysis, FT‐IR, UV–vis and NMR spectra. The molecular structure of the thiosemicarbazone (H2dsct) and its complexes have been resolved using single crystal XRD studies. In the complexes, thiosemicarbazone exist in the thioiminolate form and acts as dideprotonated tridentate ligand coordinating through phenolic oxygen, thioiminolate sulfur and azomethine nitrogen. The antibacterial activity of the prepared compounds were screened against Escherichia coli, Salmonella typhi, Enterobacter aerogenes, Shigella dysentriae, Bacillus cereus, Staphylococcus aureus. All the complexes showed activity against bacterial strains E.coli and Salmonella typhi. The thiosemicarbazone showed activity against three bacterial strains such as E. coli, Enterobacter aerogenes and Shigella dysentriae. Complex 2 showed very good antibacterial activity as compared to standard drug (Ampicillin) against the bacterial strain, Salmonella typhi. Finally, the thiosemicarbazone and its complexes have been used to accomplish molecular docking studies against an Epidermal Growth Factor Receptor (EGFR) and breast cancer mutant 3hb5‐oxidoreductase to determine the most preferred mode of interaction. The results confirm that the complex [Cu (dsct)(bipy)]·DMF(3) showed the highest docking score as compared to other complexes under study. The [Cu(dsct)(bipy)]·DMF(3) complex was evaluated for their anticancer activities against breast cancer cell line (MCF‐7) and normal L929 (Mouse Fibroblast) cell line. It was found that the compound showed an LC50 of 6.25 μg/mL against breast cancer cell line (MCF‐7).

Synthesis, spectroscopic, electrochemical characterization, density functional theory (DFT), time dependent density functional theory (TD‐DFT), and antibacterial studies of some Co(II), Ni(II), and Cu(II) chelates of (E)‐4‐(1,5‐dimethyl‐3‐oxo‐2‐phenyl‐2,3‐dihydro‐1H‐pyrazol‐4‐yl)‐1‐(3‐hydroxynaphthalen‐2‐yl)methylene) thiosemicarbazide Schiff base ligand

“…[ 96 ] On comparing the antibacterial activity of the Schiff base ligand (8.1 and 7.6 mm) with 3,5‐dichlorosalicylaldehyde‐ N 4 ‐cyclohexylthiosemicarbazone (0 and 4 mm), it can be seen that the prepared ligand exhibits more forceful activity against S. aureus and E. coli , respectively. [ 97 ] Also, comparing the antibacterial activity of compound 6 (14.6 and 13.9 mm) with [Cu(dsct)(bipy)]·DMF (0 and 8 mm), we found that the compound 6 is more efficient against S. aureus and E. coli . On comparing the zone of inhibitions of CuCl 2 compound 5 (14.8 mm) with [Cu(MnTSC) 2 ] (2.86 mm), the results show that former has better activity than the latter against the bacterial strain S. aureus .…”

Synthesis, Characterization, and Bioactivity Studies of the Schiff Base Ligand and its Zinc(II) Complex

“…While some chemical compounds may be highly biologically active on their own, they may also be quite poisonous to the organism or have poor solubility. These compounds can be coordinated with transition metal ions, such Zn(II), to increase the therapeutic effect provided by the organic part and enhance the resultant molecules' bioavailability (Mathews, Begum and Kurup, 2020), (Bazhina, et al, 2023).…”

Synthesis, Spectral, Modeling, Docking and Cytotoxicity Studies on 2‐(2‐aminobenzoyl)‐N‐ethylhydrazine‐1‐carbothioamide and its divalent metal complexes

“…The antibacterial and anticancer activities of the prepared compounds were screened. [ 10 ] The mononuclear Co (II), Ni (II), and Cu (II) chelates of the ONS tridentate ligand 4‐(1,5‐dimethyl‐3‐oxo‐2‐phenyl‐2,3‐dihydro‐1 H ‐pyrazol‐4‐yl)‐1‐(3‐hydroxynaphthalen‐2‐yl)methylene)thiosemicarbazide were synthesized and characterized. The ligand coordinated to the metal center through azomethine nitrogen, phenolate oxygen, and thione/thiolate sulfur groups.…”