Jichun Cui

Synthesis, structural characterization and in vitro cytotoxicity of diorganotin (IV) diimido complexes

Reactions of the diorganotin with two N-OH diimide ligands (N-hydroxyphthalimide and N-hydroxysuccinimide) yielded five new dimeric tetraorganostannoxanes formulated as R(8)Sn(4)O(2)L(2)X(2). The crystal structures of the complexes reveal the formation of the tetranuclear species contains a planar Sn(4)O(4) core, consisting of three adjacent rhombs with bridging oxo and N-OH diimide ligands. The central tin atoms are five-coordinated to assume a distorted trigonal bipyramidal configuration and the N-OH diimide ligands act as monodentate O-bound planar. In vitro cytotoxic activities of the title compounds have been determined against three cell lines (A549, HCT-8 and HL-60). Studies reveal that three di-n-butyltin(IV) diimido complexes show higher cytotoxic activities than cisplatin. The structure-activity relationship of the cytotoxicity of the title complexes has also been discussed.

Synthesis, structural characterization, in vitro cytotoxicities, and BSA interaction of di-organotin(IV) complexes derived from salicylaldehyde nicotinoyl hydrazone

Abstract Two organotin(IV) compounds were synthesized from salicylaldehyde nicotinoyl hydrazone and the corresponding dialkyltin(IV) precursor. Their structures were determined by IR, elemental analysis, NMR, and single crystal X-ray diffraction analysis. Compound 1 exhibits a distorted trigonal bipyramidal geometry around tin, which is coordinated to the Schiff-base ligand in an enolic tridentate fashion. For 2, structural analysis reveals that it is a centro-symmetric trimer, in which the central Sn adopts a six-coordinate octahedral geometry and the other two Sn ions adopt five-coordinate trigonal bipyramidal geometry. In vitro cytotoxicities of the compounds against three human cisplatin-resistant tumor cell lines (A549, HeLa, and MCF-7) were assessed by MTT assay. Further, the interaction of 1 and 2 with bovine serum albumin (BSA) has been explored by the titration method with fluorescence quenching spectra and synchronous fluorescence spectra. Studies reveal that di-n-butyltin(IV) complex 1 with significant antiproliferative effects in the cells shows stronger BSA interaction.

Synthesis, crystal structure, and bioactivity of two triphenylantimony derivatives with benzohydroxamic acid and N-phenylbenzohydroxamic acid

Reaction of triphenylantimony dichloride with benzohydroxamic acid or N-phenylbenzohydroxamic acid in 1 : 1 stoichiometry yielded two new triphenylantimony derivatives formulated as [Ph3SbL1L2] (L1 = benzohydroxamato, L2 = methoxide, 1; L1 = N-phenylbenzohydroxamato, L2 = Cl, 2), which have been characterized by FT-IR, NMR spectroscopy, elemental analysis, and melting point. Single-crystal X-ray diffraction analyses for 1 and 2 reveal that the antimony is six-coordinate adopting distorted octahedral geometry with one phenyl and methoxide or chloride in axial positions. In the supramolecular structure, a double-chain is shown for 2 constructed by C–H ··· X (X = O, C or π) weak interactions, while 1 exhibits a 1-D-chain structure connected by O–H ··· O and N–H ··· N hydrogen bonds. In vitro antitumor study reveals that 1 and 2 display activities against two human tumor cell lines – A549 and HCT-8. To explore the antitumor activity mechanism, DNA binding properties of 1 and 2 with calf thymus DNA (ct-DNA) have been investigated by fluorescence spectra, indicating that 1 and 2 bind to ct-DNA via intercalation, which could induce the death of cancer cells.

{4-Chloro-N′-[(2-oxidonaphthalen-1-yl-κO)methyl­idene]benzohydrazidato-κ2N′,O}di­methyl­tin(IV)

In the title complex, [Sn(CH3)2(C18H11ClN2O2)], the SnIV ion is coordinated by two O atoms and an N atom from a 4-chloro-N′-[(2-oxidonaphthalen-1-yl)methylidene]benzohydrazidate ligand and two C atoms from two methyl ligands in a distorted trigonal–bipyramidal geometry [Sn—O = 2.092 (3) and 2.144 (3) Å; Sn—N = 2.160 (4) Å]. The dihedral angle between the naphthalene ring system and the benzene ring is 8.6 (2)°. In the crystal, adjacent molecules are linked by weak C—H⋯O hydrogen bonds, forming a chain along the b-axis direction.

{1-[(2-Oxidonaphthalen-1-yl)methylidene]thiosemicarbazidato-κN,O,S}diphenyl-tin(IV).

The asymmetric unit of the title compound, [Sn(C6H5)2(C12H9N3OS)], contains two independent molecules with almost identical configurations. In each molecule, the SnIV atom is coordinated by O, N and S atoms from a (2-oxido-1-naphthaldehyde)thiosemicarbazonato ligand and two C atoms from phenyl rings in a distorted trigonal–bipyramidal geometry. Weak intermolecular N—H⋯O and N—H⋯S hydrogen bonds link four molecules into a centrosymmetric tetramer. The crystal packing exhibits short intermolecular S⋯S contacts of 3.335 (3) Å.

[2-Oxido-1-naphthaldehyde (2-hydroxy-benzo-yl)hydrazonato]diphenyl-tin(IV).

In the title compound, [Sn(C6H5)2(C18H12N2O3)], the SnIV atom has a distorted trigonal-bipyramidal geometry. The Schiff base molecule is coordinated to the SnIV atom in a tridentate fashion via the azomethine N atom, the hydroxy O atom and the carbonyl O atom. The complex involves an intramolecular O—H⋯N hydrogen bond.

{4-Amino-N′-[(2-oxidonaphthalen-1-yl)methyl­idene]benzohydrazidato}di­methyl­tin(IV)

In the title compound, [Sn(CH3)2(C18H13N3O2)], the SnIV ion is coordinated by one N and two O atoms from the tridentate 4-amino-N′-[(2-oxidonaphthalen-1-yl)methylidene]benzohydrazidate(2−) ligand and two C atoms from methyl ligands in a distorted trigonal–bipyramidal geometry. The dihedral angle between the naphthalene ring system and the benzene ring is 19.2 (2)°. In the crystal, weak N—H⋯O hydrogen bonds link the molecules into zigzag chains along [010].

trans-Tris(4-bromo-phen-yl)dichlorido-antimony(V).

The SbV atom in the title compound, [SbCl2(C6H4Br)3], has an almost regular trigonal–bipyramidal geometry with the equatorial plane made up of three C atoms of the bromophenyl groups and the axial positions occupied by two Cl− ions in a trans configuration. In the crystal, C—H⋯Br hydrogen bonds link the molecules into zigzag chains along the b-axis direction. Pairs of C—H⋯Cl hydrogen bonds further link molecules into cyclic dimers with R 2 2(10) ring motifs, generating a three-dimensional network.

[2-(4-Chloro-phen-yl)-1,3-selenazol-4-yl]methanol.

In the title compound, C10H8ClNOSe, the dihedral angle between benzene and selenazole rings is 11.4 (3)° and the hydroxymethyl group is bent from the selenazole ring, making a dihedral angle of 63.8 (3)°. In the crystal, molecules are linked into inversion dimers by pairs of O—H⋯N hydrogen bonds. Roof-tile-like stacking of the molecules along [010] [b = 4.5707 (4) Å] is observed, with the benzene and selenazole rings separated by a face-to-face distance of 3.57 Å and a mutual slippage of 2.85 Å.

(E)-4-[2-(2-Hy-droxy-benzo-yl)-hydra-zin-ylidene]penta-noic acid.

The title molecule, C12H14N2O4, adopts a trans configuration with respect to the C=N double bond. The amino group is involved in an intramolecular N—H⋯O hydrogen bond. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link the molecules into doubled sheets parallel to the (101) plane.