title: 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 and119Sn 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 H2L2and 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.
authors.affiliation: Departamento de Química Inorgánica, Universidad Autónoma de Madrid, C/ Francisco Tomás y Valiente 7, 28049 Madrid, Spain.
authors.forename: Cristina
authors.initials: C
authors.lastname: González-García
authors.affiliation: Departamento de Química Inorgánica, Universidad Autónoma de Madrid, C/ Francisco Tomás y Valiente 7, 28049 Madrid, Spain.
authors.forename: Alejandro
authors.initials: A
authors.lastname: Mata
authors.affiliation: Dipartimento di Farmacia, Università degli Studi di Parma, Parco Area delle Scienze 27/A, 43124 Parma, Italy. Electronic address: franca.zani@unipr.it.
authors.forename: Franca
authors.initials: F
authors.lastname: Zani
authors.affiliation: Departamento de Química Inorgánica, Universidad Autónoma de Madrid, C/ Francisco Tomás y Valiente 7, 28049 Madrid, Spain. Electronic address: antonia.mendiola@uam.es.
authors.forename: M Antonia
authors.initials: MA
authors.lastname: Mendiola
authors.affiliation: Departamento de Química Inorgánica, Universidad Autónoma de Madrid, C/ Francisco Tomás y Valiente 7, 28049 Madrid, Spain. Electronic address: elena.lopez@uam.es.
authors.forename: Elena
authors.initials: E
authors.lastname: López-Torres
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001412:Bacillus subtilis / Q000254:growth & development*; D006835:Hydrazones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000254:growth & development*; D013882:Thiosemicarbazones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000890:Anti-Infective Agents; D006835:Hydrazones; D013882:Thiosemicarbazones
keywords: (119)Sn NMR; Antimicrobial activity; Diorganotin(IV) complexes; Hydrazones; Thiosemicarbazones; X-ray diffraction