[Pharmacological researches of curcumin solid dispersions in treatment of cancer].

OBJECTIVE: To investigate the anticancer effect of curcumin Solid Dispersions (SDs). METHODS: Curcumin SDs were prepared by patent technology. The anticancer effect of curcumin SDs were investigated by vivo and vitro tests of SCG-7901, BEL-7402, S-180 and Ehrlich ascites tumor models. RESULTS: The results showed that Curcumin SDs had markedly anticancer effect and could improve the anticancer effect of cisplatin. CONCLUSION: Curcumin SDs could be developed into one kind of adjuvant drug for anticancer, as it has markedly anticancer effect, and could improve the anticancer effects of cisplatin.

Trinuclear and mononuclear copper(II) complexes incorporating tetradentate 2,2'-[1,1'-(ethylenedioxydinitrilo)diethylidyne]diphenol ligand: Syntheses, crystal structures, spectral and thermal behaviors.

Mononuclear and trinuclear Cu(II) complexes with chemical formula [CuL].CH3OH (1) and [{(Cu(mu-L))2(OAc)2}Cu] (2), where H2L = 2,2'-[1,1'-(ethylenedioxydinitrilo)diethylidyne]diphenol, have been synthesized and characterized by elemental analyses, 1H NMR, IR and UV-vis spectra et al. Crystallographic data of complex 1 reveal the formation of an asymmetric mononuclear structure and a slight distortion toward tetrahedral geometry from the square planar structure, in which the introduction of the non-coordinated methanol molecule lead to the assembly of the 1D chains by hydrogen bonding, Cu...pi and pi...pi interactions. Complex 2 have the elongated square pyramidal geometries for the two terminal Cu(II) ions and an octahedral coordinated geometry for the central Cu(II) ion. In complex 2, two acetate ions coordinate to three Cu(II) ions adopting a familiar syn-syn (muM-O-C-O-M) coordinated fashion. The central Cu(II) ion sits in a crystallographic inversion centre. Therefore, the whole molecule of complex 2 is rigorously centrosymmetric, and forms a 3D supramolecular networks through intermolecular C-H...O and C-H..pi interactions.

6,6'-Dihydr-oxy-2,2'-[(butane-1,4-diyldi-oxy)bis-(nitrilo-methyl-idyne)]diphenol.

The mol-ecule of the centrosymmetric title compound, C(18)H(20)N(2)O(6), assumes an E configuration with respect to the azomethine C=N bond. The imino group is coplanar with the aromatic ring. Intra-molecular O-H⋯O and O-H⋯N bonds are found between the hydroxyl groups and adjacent O (or N) atoms. In the crystal structure, inter-molecular O-H⋯O bonds link each mol-ecule to two others, forming a layered network.

Bis{µ-5-(diethyl-amino)-2-[(2-oxidoeth-oxy)imino-meth-yl]phenolato}dicopper(II) acetone solvate.

The title complex, [Cu(2)(C(13)H(18)N(2)O(3))(2)]·C(3)H(6)O, has been synthesized by the reaction of copper(II) acetate monohydrate with 5,5'-bis-(diethyl-amino)-2,2'-[ethyl-enedioxy-bis(nitrilo-methyl-idyne)]diphenol, where one of the N-O bonds of the ligand was cleaved during the reaction. The complex mol-ecule has a µ-dialkoxo-bridged binuclear structure with both Cu(II) centers exhibiting a square-planar coordination geometry.

2,2'-Dichloro-1,1'-[(butane-1,4-diyldi-oxy)bis-(nitrilo-methyl-idyne)]dibenzene.

The mol-ecule of the title compound, C(18)H(18)Cl(2)N(2)O(2), lies across a crystallographic inversion centre and adopts an E configuration with respect to the azomethine C=N bond. The imino group is coplanar with the aromatic ring. Within the mol-ecule, the planar units are parallel, but extend in opposite directions from the dimethyl-ene bridge. In the crystal structure, the title compound exhibits a layer packing structure via weak π-π stacking inter-actions [inter-molecular plane-to-plane distances between adjacent aromatic rings are 3.461 (3) Å]. Mol-ecules in each layer are linked by inter-molecular C-H⋯O hydrogen-bonding inter-actions.

2,2'-[1,1'-(Hexane-1,6-diyldioxy-dinitrilo)diethyl-idyne]diphenol.

The molecule of the title compound, C(22)H(28)N(2)O(2), lies across an inversion centre with one half-mol-ecule in the asymmetric unit. The mol-ecule adopts an E configuration with respect to the azomethine C=N bond and the imino group is coplanar with the aromatic ring. Within the mol-ecule, the planar units are parallel, but extend in opposite directions from the hexa-methyl-ene bridge. There are intra-molecular O-H⋯N hydrogen bonds between the hydroxyl groups and the oxime N atoms. There are also weak inter-molecular C-H⋯O bonds that link each mol-ecule to two others, forming chains along the a axis.

6,6'-Dihydr-oxy-2,2'-[(propane-1,3-diyl-dioxy)bis-(nitrilo-methyl-idyne)]diphenol.

The mol-ecule of the title compound, C(17)H(18)N(2)O(6), adopts a V-shaped conformation, the dihedral angle between the two halves of the mol-ecule being 81.31 (4) °. There is one half-mol-ecule in the asymmetric unit, with a crystallographic twofold rotation axis passing through the central C atom. There are strong intra-molecular O-H⋯N and O-H⋯O hydrogen bonds involving the hydr-oxy group and adjacent O and N atoms. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules, forming an infinite three-dimensional supra-molecular structure.

5,5'-Bis(diethyl-amino)-2,2'-[butane-1,4-diyldioxy-bis(nitrilo-methyl-idyne)]-diphenol.

The title complex, C(26)H(38)N(4)O(4), was synthesized by the reaction of 4-diethyl-amino-2-hydroxy-benzaldehyde with 1,4-bis-(amino-oxy)butane in ethanol. It crystallizes as discrete centrosymmetric molecules adopting an extended conformation where the two salicylaldoxime groups are separated from each other. Intra-molecular O-H⋯N hydrogen bonding is observed between the hydr-oxy groups and oxime N atoms. Inter-molecular π-π stacking inter-actions [3.979 (2) Å] between aromatic rings are apparent in the crystal structure. Each ethyl group is disordered over two positions; in one the site occupancy factors are 0.55 and 0.45, in the other 0.53 and 0.47.

2,2'-[1,1'-(Propane-1,3-diyldioxy-dinitrilo)diethyl-idyne]diphenol.

The title compound, C(19)H(22)N(2)O(4), was synthesized by the reaction of 2'-hydroxy-acetophenone with 1,3-bis-(amino-oxy)propane in ethanol. Intra-molecular O-H⋯N and weak C-H⋯O hydrogen bonds stabilize the three-dimensional structure. A twofold rotation axis passes through the molecule.

1,1'-[(Hexane-1,6-diyldi-oxy)bis-(nitrilo-methyl-idyne)]dinaphthalene.

The title compound, C(28)H(28)N(2)O(2), was synthesized by condensation of 1-naphthaldehyde with 1,6-bis-(amino-oxy)hexane in ethanol. The mol-ecule is disposed about a crystallographic centre of symmetry. In the crystal structure, mol-ecules are linked through strong inter-molecular π-π stacking inter-actions [interplana distance = 2.986 (2) Å], forming a three-dimensional network.

2,2'-Dichloro-1,1'-[(propane-1,3-diyldi-oxy)bis-(nitrilo-methyl-idyne)]dibenzene.

The title compound, C(17)H(16)Cl(2)N(2)O(2), assumes a V-shape configuration with a dihedral angle between the two halves of the mol-ecule of 79.60 (4)°. The asymmetric unit comprises one half-mol-ecule with a crystallographic twofold rotation axis passing through the central C atom. There are weak inter-molecular π-π stacking inter-actions between neighbouring benzene rings with inter-molecular plane-to-plane distances of 3.277 (6) and 3.465 (5) Šalong the a and c axes, respectively. In the crystal structure, weak inter-molecular C-H⋯O bonds link each mol-ecule to four others to form an infinite three-dimensional network.

6,6'-Dihydr-oxy-2,2'-[(pentane-1,5-diyl-dioxy)bis-(nitrilo-methyl-idyne)]diphenol.

The mol-ecule of the title compound, C(19)H(22)N(2)O(6), assumes a W-shaped configuration with the dihedral angle between the two halves of the mol-ecule being 82.48 (5)°. There is one half-mol-ecule in the asymmetric unit with a crystallographic twofold rotation axis passing through the central C atom of the five methylene groups in the [-CH=N-O-(CH(2))(5)-O-N=CH-] bridge. The dihedral angle formed by the two benzene rings in each mol-ecule of the title compound is 84.18 (4)°. There are strong intra-molecular O-H⋯N and O-H⋯O hydrogen bonds and weak inter-molecular π-π stacking inter-actions between neighbouring benzene rings, and the inter-molecular plane-to-plane distances are 3.488 (2) and 3.841 (3) Šalong the b and c axes, respectively. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link each mol-ecule to two others, forming an infinite three-dimensional supra-molecular structure.

2,2'-{1,1'-[Pentane-1,5-diyl-bis(oxy-nitrilo)]-diethyl-idyne}diphenol.

In the title compound, C(21)H(26)N(2)O(4), there is half a mol-ecule in the asymmetric unit with a crystallographic twofold rotation axis passing through the central C atom of the -CH=N-O-(CH(2))(5)-O-N=CH- bridge. The dihedral angle formed by the two benzene rings is 80.85 (2)°. Strong intra-molecular O-H⋯N and C-H⋯O hydrogen bonds help to establish the molecular conformation. There are also weak inter-molecular π-π stacking inter-actions between neighbouring benzene rings [centroid-centroid separation = 3.502 (3) Å].