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Synthesis, structural description and antimicrobial activities of thioether based Schiff bases and their dinuclear
Raymond Akong Akong1, Helmar Görls2, Joseph Anthony Orighomisan Woods3
1Inorganic Chemistry Unit, Department of Chemistry, Faculty of Science, University of Ibadan, Ibadan, Nigeria; Institut für Anorganische und Analytische Chemie, Friedrich-Schiller-Universität Jena, Humboldtstrasse 8, 07743 Jena, Germany.
Abstract:
We report a series of dinuclear cobalt complexes of composition [Co2(L1-8)2]·nS {S = solvent} (1-8) obtained from bis-phenol pentadentate Schiff bases (H2L1 - H2L8). The compounds were characterised via nuclear magnetic resonance (nmr), spectroscopic (infrared, electronic and mass spectroscopy) techniques as well as elemental analysis. The structures of 1·(MeCN), 2, 4·(3THF), 6·(4DCM), 7·(THF), 8 and H2L7 were confirmed via single crystal X-ray crystallography. Modifications on the phenoxyl ring of 1·(MeCN) induces deviation from ideal octahedral geometry and substitution of S-donor atom {in 1·(MeCN)} with O-donor atom {in 8} resulted in a five-coordinate square pyramidal geometry. Evaluation of the compounds against selected Gram(+), Gram(-) and fungi strains generally indicated moderate activities against tested organisms. The ligands and complexes displayed better activities againstK. pneumoniaethan E. coli. Some of the compounds displayed comparable activities to ciprofloxacin against B. subtilisandK. pneumoniaeas well as ketoconazole against T. rubrum. The compounds are therefore viable alternatives against microbial resistance. Molecular docking was used to predict the conformations and poses of the compounds against S. aureus, MenAT1 toxin-antitoxin from Mycobacterium tuberculosisand C. albicans receptors. The methyl (H2L3) and vanillin (H2L7) based ligands gave better docking scores than ciprofloxacin (with S. aureus) while the phenanthrene (H2L2) based ligand gave better docking score than ketoconazole (with C. albicans). The five-coordinate O-donor, 8, appears to give more favourable docking interactions with the receptors than the six-coordinate analogues.
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