Amino Acid‐Based Cinnamoyl Thiourea Ligands and Their Copper(II) Complexes: Synthesis, in Silico, and Antibacterial Evaluation
Abstract
ABSTRACT Three amino acid‐based cinnamoyl thiourea compounds ( 1–3 ) as potential antimicrobial agents has been synthesized, focusing on optimizing their pharmacokinetic profiles. Molecular docking simulations against the DNA gyrase enzyme (PDB ID: 1KZN) yielded encouraging results, with docking scores between −5.7 and −7.1 kJ mol −1 . The ligands also demonstrated favorable drug‐like properties, obeying Lipinski's rule of five and showing predictions for high gastrointestinal absorption and low blood–brain barrier (BBB) permeability. Interestingly, the corresponding Cu(II) complexes ( 1a–3a ) exhibited even stronger binding affinities, with docking scores ranging from −7.2 to −8.2 kJ mol −1 . The successful synthesis of the thiourea ligands was confirmed by FTIR spectroscopy which displayed characteristic N─H and C═S stretches at 3165–3056 cm −1 and 1293–1269 cm −1 , respectively. In the 1 H NMR spectra, the presence of CONH and CSNH signals in the δ 11.43–11.13 ppm region further supported the proposed structures. The formation of the Cu(II) complexes was confirmed by the disappearance of the carbonyl band of the carboxylate group at 1731–1716 cm −1 in the FTIR spectra indicated that the carboxylate group coordinated with the Cu(II) center. Antibacterial assays showed that compound 2 , complexes 1a and 2a , possessed promising activity against the E. coli strain, producing clear inhibition zones of 10–13 mm.
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Evidence Hub reads this as a simulation / modelling, done in computer models (in silico), not in people. Its evidence level is 5 of 5 (Very low · case / narrative / animal / in vitro / in silico). Case reports, narrative reviews, and animal, cell or computer-model studies give the weakest evidence for human health.
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