Synthesis, Characterization, Crystal Structure And Biological Activity Of A Novel Derivatives Of Thiazolidinones

In this paper, using salicylic acid compounds as raw materials, we have synthesized four4-thiazolidone ligands of different substituents. Such as:（Z）-2-hydroxy-N’-（4-oxothiazolidin-2-ylidene）benzohydrazide,（Z）-2-hydroxy-4-methyl-N’-（4–oxothiazolidin-2-ylidene） benzohydrazide,（Z）-5-chloro-2-hydroxy-N’-（4-oxothiazolidin-2-ylidene）benzohydrazide,（Z）-5-bromo-2-hydroxy-N’-（4-oxothiazolidin-2-ylidene）benzohydrazide. Furthermore, we have synthesized two metal complexes with iron, nickel,and got two ligands crystals and two complex crystals. Element analysis, IR, NMR and othermethods were used to characterize the compounds, and crystals was characterized by X-raycrystal diffraction. Finally, we have assayed anti-inflammatory and antibacterial bioactivity ofthe all compounds.X-Ray single crystal diffraction measurements were used to characterize the crystals ofC₁₀H₉N₃O₃S, C₁₁H₁₇N₃O₆S,[Ni^IIINi^II3(C₁₀H₆N₃O₃S)₃（C₂H₇N）3]·（C₃H₇NO）·（C₂H₇N）·7/2H2O,[Fe₈(C₁₀H₅ClN₃O₃S)₈（H₂O）₈]·8（C₃H₇NO）·30H2O. The crystallographic data are as follows:The ligand of C₁₀H₉N₃O₃S has been determined in the crystal system monoclinic, spacegroup C2/c, with a=18.788（2）, b=8.9334（10）, c=12.7969（14）, α=90, β=92.677（2）,γ=90, V=2145.6（4）3, Z=8, Dcalc=1.556mg/m³, R₁=0.039334, wR₂=0.1079,GOF=1.076.The ligand of C₁₁H₁₇N₃O₆S has been determined in the crystal system triclinic, spacegroup P-1, with a=7.3739（12）, b=8.5110（13）, c=12.493（2）, α=103.047（2）, β=101.385（2）, γ=92.532（2）, V=745.5（2）3, Z=2,1.423Dcalc=1.423mg/m³,R₁=0.0531, wR₂=0.1521,GOF=1.103.The complex of [Ni^IIINi^II3(C₁₀H₆N₃O₃S)₃（C₂H₇N）3]·（C₃H₇NO）·（C₂H₇N）·7/2H₂O istetranuclear cluster which has been determined in the crystal system monoclinic. The crystalsystem monoclinic space group P2（1）/c, with a=30.634（2）, b=15.3944（11）, c=26.3403（18）, α=90, β=101.305（2）,γ=90，V=12180.8（15）3, Z=8, Dcalc=1.413mg/m³,R₁=0.0699, wR₂=0.2416,GOF=1.145.The complex of [Fe₈(C₁₀H₅ClN₃O₃S)₈（H₂O）₈]·8（C₃H₇NO）·30H₂O is a octanuclearcluster which has been determined in the crystal system Orthorhombic, space group I222,with a=22.983（3）, b=23.487（3）, c=37.039（8）, α=90, β=90, γ=90, V=19994（6）3,Z=4, Dcalc=1.321mg/m³, R₁=0.1140, wR₂=0.2924,GOF=1.261.Using the mouse palmar paw swelling method proposed by Kasahara, we have studiedanti-inflammatory activity of6compounds of ligands and complexes. We found that they all have good anti-inflammatory activity, and anti-inflammatory effects than diflunisal, and thecomplex of [Fe₈(C₁₀H₅ClN₃O₃S)8（H2O）8]·8（C₃H₇NO）·30H₂O has the strongest anti-inflammatory activity,（Z）-2-hydroxy-N’-（4-oxothiazolidin-2-ylidene）benzohydrazide has theweakest anti-inflammatory activity.By using concentration dilution methed, we have tested the antibacterial activity of the6ligands and complexes against four kinds of bacteria （Staphylococcus glucose Staphylococcus,Escherichia coli, Bacillus subtilis, Proteus vulgaris）. The results show that they have differentdegrees of inhibition against four kinds of bacteria. In general, the effect againstStaphylococcus aureus inhibition is the best, but Bacillus subtilis inhibitory effect is poor. Andbacteriostasis effect of [Ni^IIINi^II3(C₁₀H₆N₃O₃S)₃（C₂H₇N）3]·（C₃H₇NO）·（C₂H₇N）·7/2H2Ocomplexes is strongest, the ligand of （Z）-5-bromo-2-hydroxy-N’-（4-oxothiazolidin-2-ylidene） benzohydrazide has the best bacteriostatic effect.