Synthesis and antimicrobial activity of tetradentate ligands bearing hydrazone and/or thiosemicarbazone motifs and their diorganotin(IV) complexes

Abstract

Four novel ligands derived from 2,3-butanedione have been synthesized, two dissymmetric thiosemicarbazone/3-hydroxy-2-naphthohydrazone ligands, H₂L¹ (bearing 4-isopropyl-3-thiosemicarbazone) and H₂L² (containing 4-cyclohexyl-3-thiosemicarbazone) and the symmetric H₂L³, diacetyl bis(3-hydroxy-2-naphthohydrazone), and H₂L⁴, diacetyl bis(4-cyclohexyl-3-thiosemicarbazone). Their reactivity with SnR₂Cl₂ (R=methyl, n-butyl and phenyl) was explored and the resulting complexes were characterized by elemental analysis, molar conductivity, mass spectrometry, IR, ¹H, ¹³C and ¹¹⁹Sn NMR and seven of them also by single crystal X-ray diffraction. The results showed that the reactivity of the dissymmetric ligands is strongly different and while the cyclohexyl derivative is very stable, with isopropyl easily undergoes a symmetrization reaction to yield the corresponding symmetric ligands. The antimicrobial activity of the ligands and the corresponding diorganotin(IV) complexes was investigated in vitro against seven species of microorganisms and minimum inhibitory concentrations (MICs) were determined. The results showed that the ligand H₂L² and several of its derivatives, together with methyl and phenyl complexes of H₂L¹, have the ability of inhibiting the growth of tested bacteria and fungi to different extents. Bacillus subtilis and Staphylococcus aureus Gram positive strains were the most sensitive microorganisms.

Keywords: (119)Sn NMR; Antimicrobial activity; Diorganotin(IV) complexes; Hydrazones; Thiosemicarbazones; X-ray diffraction.