Hai-Liang Zhu

Synthesis, structure, and biological evaluation of three Cu(II) and Ni(II) (E)-3-(3,4-dimethoxyphenyl)acrylate complexes with organic diamines as potential urease inhibitors

Three new complexes (1–3) have been synthesized and characterized by X-ray single crystal determination and evaluated for inhibitory activity on jack bean urease. All the complexes contained a new cinnamic acid derivative as the ligand (C11H12O4), (E)-3-(3,4-dimethoxyphenyl)acrylic acid, and crystallized in monoclinic C2/c space group. Complex 1 (C11H11O4)4(C3N2H8)2Cu2 (C3N2H8 = 1,2-diaminopropane) was obtained with a = 20.488(2), b = 19.596(2), c = 15.2500(13), β = 93.502(2)°, V = 6111.2(10) Å3, Z = 4, R 1  = 0.0616, and wR 2  = 0.2059. Complex 2 (C11H11O4)4(C3N2H8)2Cu2 (C3N2H8=1,3-diaminopropane) was obtained with a = 20.2494(12), b = 19.5732(12), c = 14.8940(8), β = 96.884(2)°, V = 5860.6(6) Å3, Z = 4, R 1  = 0.0409, and wR 2  = 0.1107. Complex 3 (C11H11O4)2(C2N2H6)2Ni2·H2O (C2N2H6 = ethylenediamine) was obtained with a = 28.359(2), b = 6.5422(5), c = 16.8587(14), β = 101.359(2)°, V = 3066.5(4) Å3, Z = 4, R 1  = 0.0422, and wR 2  = 0.1190. It was found that copper(II) complexes 1 [IC50 = 4.71 μM] and 2 [IC50 = 3.15 μM] showed strong inhibitory activity against jack bean urease compared with acetohydroxamic acid [IC50 = 10.01 μM] as a positive reference. Unfortunately, 3 exhibited no inhibitory activity.

Syntheses, Crystal Structures, Thermal Stability, and Fluorescence Properties of Zinc(II) Complexes With Tridentate Schiff Bases

Two new mononuclear Schiff base zinc(II) complexes, [Zn (NMP)(MeCOO)] (1) and [ZnBr2(MP)]·MeOH·H2O (2) (NMP = 4-nitro-2-[(3-morpholin-4-ylpropylimino)methyl]phenolate; MP = 2-[(3-morpholin-4-ylpropylimino)methyl]phenolate), have been synthesized from the similar tridentate Schiff base ligands. The complexes were characterized by elemental analysis, infrared spectra, and single-crystal X-ray diffraction. The Zn atom in 1 is five-coordinated in a distorted Squire-pyramidal geometry by the NNO donor set of NMP and two O atoms of an acetate ligand. The Zn atom in 2 is four-coordinated in a tetrahedral geometry by the imino N and phenolate O atoms of MP and two Br atoms. The thermal stability and fluorescence properties of the complexes have also been determined.

Synthesis, crystal structures, and fluorescent properties of zinc and cadmium(II) complexes with tridentate Schiff bases

A new dinuclear zinc(II) complex, [Zn2(L1)2(N3)2] (1), and a new polynuclear cadmium(II) complex, [Cd2(L2)2(NO3)(μ2-dca)]n (2), where L1 and L2 are deprotonated forms of 2-[(2-ethylaminoethylimino)methyl]-6-methylphenol and 2-[(2-ethylaminoethylimino)methyl]-4-methoxyphenol, respectively, have been prepared and characterized by elemental analysis, IR spectra, and single crystal X-ray diffraction. The thermal stability and fluorescence of the complexes were also investigated.

Synthesis and biological evaluation of Cu(II), Zn(II), and Ni(II) 3-(4-nitrophenyl)acrylic acid complexes with diamines as potential urease inhibitors

Five new Cu(II), Zn(II), and Ni(II) 3-(4-nitrophenyl)acrylic acid complexes were synthesized and evaluated for inhibitory activity on jack bean urease. All five complexes were structurally determined by single crystal X-ray analysis. Compared with the positive reference acetohydroxamic acid (IC50 = 13.25 μM), Cu(II) complexes 3 and 4 showed the strongest inhibitory activity against jack bean urease (IC50 = 1.23 and 1.17 μM). Ni(II) and Zn(II) complexes also exhibited inhibitory activities (IC50 = 10.09–13.10 μM).

Synthesis, structure, urease inhibitory, and cytotoxic activities of two complexes with protocatechuic acid derivative and phenanthroline

Two complexes, [CuII(L1)(phen)2](ClO4) (1) and [NiII2(L1)2(phen)2(MeOH)2](ClO4)2 (2), with HL1, a ligand derived from protocatechuic acid (=2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylic acid) and phen (=1,10-phenanthroline) were synthesized and characterized by C, H, and N elemental analysis, UV–vis, FT-IR, and single-crystal X-ray diffraction, which revealed that 1 is mononuclear and 2 is dinuclear. Both complexes crystallized in monoclinic space group C2/c. The urease inhibitory activity and in vitro cytotoxic activity of 1 and 2 were tested. The complexes showed strong inhibitory activity against jack bean urease and significantly suppressed the growth of A549, L929, and SW620 cell lines.

Syntheses, Crystal Structures and Antimicrobial Activities of Vanadium(V) Complexes with Similar Tridentate Hydrazone Ligands ①

Two new oxovanadium(V) complexes, [VOL1(OEt)(EtOH)] (1) and [VOL2(OMe)(MeOH)] (2), were prepared by reaction of [VO(acac)2] (where acac = acetylacetonate) with N′-(3-bromo-2-hydroxybenzylidene)-4-methylbenzohydrazide (H2L1) in ethanol and N′-(3-bromo-2-hydroxybenzylidene)-4-methoxybenzohydrazide (H2L2) in methanol, respectively. Crystal and molecular structures of the complexes were determined by elemental analysis, infrared spectra, and single-crystal X-ray diffraction. The V ions have octahedral coordination. Thermal stability and the inhibition of urease of the complexes were studied. Graphical Abstract

Synthesis, crystal structures, and magnetic properties of tetranuclear nickel(II) and copper(II) complexes with tridentate Schiff bases

Two cubane-type tetranuclear nickel(II) and copper(II) complexes, [Ni4(L1)4(CH3OH)4] (1) and [Cu4(L2)4]·H2O (2), where L1 and L2 are the dianionic forms of the tridentate Schiff bases 4-nitro-2-[(2-hydroxyethylimino)methyl]phenol (H2L1) and 5-methoxy-2-[(2-hydroxyethylimino)methyl]phenol (H2L2), respectively, have been synthesized and characterized by physicochemical methods and single-crystal X-ray diffraction. The magnetic properties of the complexes show the presence of ferromagnetic interactions for complex 1 and antiferromagnetic interactions for complex 2, mediated by hydroxyl bridges.

Discovery of phenylpiperazine derivatives as IGF-1R inhibitor with potent antiproliferative properties in vitro.

A series of phenylpiperazine derivatives (3a-3q) were designed and synthesized. In vitro assays indicated that several phenylpiperazine derivatives had excellent antiproliferative properties against four cancer cell lines including multidrug-resistant cancer cell lines, with IC50 values in the low micromolar range. The average IC50 of the most active compound 3b is 0.024μM to the MCF-7 cell line. In addition, the mechanism of action of these new analogues was investigated by molecular docking studies, insulin-like growth factor 1-receptor (IGF-1R) kinase assay and apoptosis induced assay. These studies confirmed that these new phenylpiperazine derivatives maintain their mechanisms of action by disrupting IGF-1R kinase.

Synthesis, structure, and urease inhibitory activities of three binuclear copper(II) complexes with protocatechuic acid derivative

Three Cu(II) complexes, [CuII2(L1)4(L2)2] (1), [CuII2(L1)4(H2O)2]·HL (2), and [CuII2(L1)3(L3)2]ClO4 (3), with a ligand derived from protocatechuic acid (HL1 = C9H8O4=2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylic acid, L2 = C7H9N=o-toluidine, L3 = C6H16N2=N,N-diethylethylenediamine) were synthesized and characterized by C, H, and N elemental analysis and single-crystal X-ray diffraction, which revealed that the three complexes have similar binuclear structures. Complexes 1 and 3 crystallized in triclinic space group P-1 and 2 in orthorhombic space group P212121. The urease inhibitory activities of the three complexes were tested. All three complexes showed strong inhibitory activity against jack bean urease with an IC50 value of 6.8, 5.5, and 3.5 μM compared with the acetohydroxamic acid (IC50 = 7.5 μM), which was a positive control. Graphical Abstract

Syntheses and Crystal Structures of Cobalt(III) and Manganese(III) Complexes With bis-Schiff Bases

A new mononuclear Schiff base cobalt(III) complex, [Co(MEA) (N3)(DMF)] (1), and a new mononuclear Schiff base manganese(III) complex, [Mn(EEA)(N3)(OH2)] (2) (MEA is bis (5-methoxysalicylidene)ethylenediamine; EEA is bis(6-ethoxys alicylidene)ethylenediamine), have been prepared and structurally characterized by physicochemical and single-cyrstal X-ray diffraction. Complex 1 crystallizes in the monoclinic space group P21/c with unit cell dimensions a = 9.910(1) Å, b = 19.279(1) Å, c = 12.410(1) Å, β = 102.729(2)°, V = 2312.8(2) Å3, Z = 4, R 1 = 0.0319, and wR 2 = 0.0779. Complex 2 crystallizes in the monoclinic space group P21/c with unit cell dimensions a = 14.252(2) Å, b = 22.227(3) Å, c = 13.613(2) Å, β = 91.512(2)°, V = 4310.7(11) Å3, Z = 8, R 1 = 0.0392, and wR 2 = 0.0839. The metal atom in each complex is in an octahedral coordination. Crystal of complex 2 was stabilized by hydrogen bonds.