Nickel(II) complex of polyhydroxybenzaldehyde N4-thiosemicarbazone exhibits anti-inflammatory activity by inhibiting NF-κB transactivation.

Background: The biological properties of thiosemicarbazone have been widely reported. The incorporation of some transition metals such as Fe, Ni and Cu to thiosemicarbazone complexes is known to enhance its biological effects. In this study, we incorporated nickel(II) ions into thiosemicarbazone with N4-substitution groups H3L (H; H3L1, CH3; H3L2, C6H5; H3L3 and C2H5; H3L4) and examined its potential anti-inflammatory activity.

(6-Hydroxy-2-{[2-(N-methyl-carbamo-thiol-yl)hydrazin-1-yl-idene-κN,S]meth-yl}-phenolato-κO)(triphenyl-phosphane-κP)nickel(II) chloride.

The deprotonated Schiff base ligand in the title salt, [Ni(C(9)H(10)N(3)O(2)S)(C(18)H(15)P)]Cl, functions as an N,O,S-chelating anion to the phosphine-coordinated nickel(II) atom, which exists in a distorted square-planar geometry. The hy-droxy group forms an intra-molecular O-H⋯O hydrogen bond. The two amino groups of the cation are hydrogen-bond donors to the chloride anion; the hydrogen bonds generate a chain structure running along the b axis.

(E)-1-(2,4,6-Trihy-droxy-benzyl-idene)-4-ethyl-thio-semicarbazide dihydrate.

In the title mol-ecule, C(10)H(13)N(3)O(3)S·2H(2)O, the thio-semi-carbazide =N-NH-C(=S)-NH- fragment [torsion angle = 0.2 (1)°] is nearly coplanar with the benzene ring [dihedral angle = 2.4 (1)°].

{2-[(2-Carbamothiol-ylhydrazin-1-yl-idene-κN,S)meth-yl]-6-hy-droxy-phenolato-κO}(triphenyl-phosphine-κP)nickel(II) chloride.

The deprotonated Schiff base ligand in the title compound, [Ni(C(8)H(8)N(3)O(2)S)(C(18)H(15)P)]Cl, functions as an N,O,S-chelating anion to the phosphine-coordinated Ni atom, which exists in a distorted square-planar geometry. The hy-droxy group forms an intra-molecular O-H⋯O hydrogen bond. The two amino groups of the cation are hydrogen-bond donors to the chloride anion; the hydrogen bonds generate a chain structure running along the b axis.

1-(2,3,4-Trihydroxy-benzyl-idene)thio-semicarbazide.

In the title mol-ecule, C(8)H(9)N(3)O(3)S, the thio-semicarbazide =N-NH-C(=S)-NH- fragment is twist a different degree of twist in the three independent mol-ecules [dihedral angles = 7.6 (1), 11.6 (1) and 20.

1-(2,3,4-Trihydroxy-benzyl-idene)-4-ethyl-thio-semicarbazide.

In the title mol-ecule, C(10)H(13)N(3)O(3)S, the thio-semicarbazide =N-NH-C(=S)-NH- fragment is twisted with respect to the aromatic ring [dihedral angle = 20.5 (1)°]. A weak N-H⋯S hydrogen bond [3.