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Tetra-coordinated nickel(II) complexes of two ONS (1, 2) and seven ONN (3a-3g) chelating 2-hydroxy-3-methoxy-benzaldehyde thiosemicarbazones were synthesized. The dibasic ligands and complexes bearing PPh 3 as a coligand were characterized by means of analytical and spectroscopic data. Cytotoxic activities of the ligands and nickel(II) complexes were determined using the MTT assay in vitro against MDCK cells, and then all the compounds were tested on influenza virus replication by plaque assays. The compounds showed GI 50 values varying from concentrations of 15.9 up to 161.8 µ g/mL for MDCK cells. The plaque assays indicated that one ONS (1) and two ONN (3c and 3d) chelate structures have considerable antiviral effects on influenza A viruses at lower concentrations than the GI 50 values for MDCK cells. The ligands and other complexes did not show any inhibitory effects on influenza virus plaque formation. The effects of the compounds on the influenza virus and structure-antiviral activity relationships were discussed based on the donor atoms and S-alkyl substituents.

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Reactions of 5-bromo-2-hydroxy-benzaldehyde-S-R-4-R 1 -thiosemicarbazones, [R, R 1 = H,H (L 1 ); CH 3 , H (L 2 ); H, C 6 H 5 (L 3 ); CH 3 , C 6 H 5 (L 4 )] with [Ni(PPh 3 ) 2 Cl 2 ] in 1:1 molar ratio yielded complexes of general formula [Ni(L)(PPh 3 )]. While the complexes of L 1 and L 3 involve the ONS donor set of the thiosemicarbazone, the L 2 complexes utilize the ONN set. The reaction of L 4 and the nickel salt gave the L 3 complex by loss of the CH 3 group from the sulphur. The complexes were characterized by physicochemical and spectroscopic methods. The structures of the L 1 and L 2 complexes have been determined by single crystal X-ray diffraction and a new coordination mode (ONN) of salicylaldehyde thiosemicarbazones has been identified.Electronic supplementary material The online version of this article (

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