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Synthesis and structural characterisation of novel linked bis(beta-diketiminato) rare earth metal complexes

Rare earth metal complexes based on novel linked bis(beta-diketiminato) ligands have been prepared via amine elimination and their structural characterisation revealed that the linker unit has significant influence on the geometry and coordination mode of the ancillary ligand. The Royal Society of Chemistry 2005.

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MK2 INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

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Synthesis, characterization and cytotoxicity of new gold(III) complexes with 1,2-diaminocyclohexane: Influence of stereochemistry on antitumor activity

Gold(III) complexes of the type [(DACH)AuCl2]Cl, derived from sodium tetrachloroaurate(III) dihydrate NaAuCl4¡¤2H 2O, where DACH is diaminocyclohexane, have been synthesized. These potential metallodrug compounds were characterized using various spectroscopic and analytical techniques, including elemental analysis, UV-Vis, infrared spectroscopy, solution as well as solid NMR spectroscopy and X-ray crystallography. The potential of the synthesized gold(III) complexes as anti-cancer agents was investigated by measuring some relevant physicochemical and biochemical properties, such as the stability of the Au-N bonds by vibrational stretching from far-IR as well as cytotoxicity and the stomach cancer cell inhibiting effect. The solid-state 13C NMR chemical shift shows that the ligand is strongly bound to the gold(III) center via N atoms. An X-ray crystallography study of the complexes shows that the cyclohexyl ring adopts a chair conformation and the gold coordination sphere adopts a distorted square planar geometry. The cis isomer in solution showed higher activity towards the inhibitory effect of human cancer cell lines such as prostate cancer (PC-3) and gastric carcinoma (SGC-7901) than that of the trans isomer. The cytotoxicity of the cis isomer complex has also been estimated in PC-3 and SGC-7901 cells.

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Sulfinamides as highly effective amine protecting groups and their use in the conversion of Amino alcohols into morpholines

1,2-Amino alcohols have been converted into morpholines by using sulfinamides as temporary protecting/activating groups on the amine. We have developed a procedure for the selective synthesis of monoprotected N-sulfinyl amino alcohols through a double sulfinylation/hydrolysis strategy. Following the reaction of the sulfinamides with bromoethyldiphenylsulfonium triflate, protected morpholines were obtained in high yields. Subsequent treatment with HCl liberated the morpholine hydrochloride salts. The usefulness of this high yielding and efficient methodology has been demonstrated in the formal synthesis of the antidepressant drug (S,S)-reboxetine. Copyright

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Syntheses of Square-planar Nickel-(II) and -(I) Complexes of an Octaaza Macrohexacyclic Ligand and Crystal Structure of the Nickel(II) Complex

The square-planar nickel(II) complex of the octaaza macrohexacyclic ligand 1,3,6,8,10,12,15,17-octaazahexacyclo<15.6.1.1 3,17 .1 6,0 .1 8,12 .0 18,23 >heptacosane, 2, has been synthesized by template condensation of the nickel(II) complex of 3,7-bis(2-aminoethyl)-1,3,5,7-tetraazabicyclo<3.3.1>nonane with formaldehyde and trans-cyclohexane-1,2-diamine.The complex exhibits an unusually strong ligand-field strength compared with other square-planar nickel(II) complexes of 14-membered azamacrocycles.Cyclic voltammetry indicated a one-electron reduction potential at -1.32 V vs.Ag-AgCl and no oxidation peak up to +1.59 V.The complex crystallizes in the orthorhombic space group Pna2 1 , with a = 17.934(2), b = 16.056(3), c = 9.612(1) Angstroem and Z = 4.The structure was solved by the heavy-atom method and refined by full-matrix least squares to a final R = 0.0447 for 2092 observed 2?(I)> reflections.The ligand contains bicyclononane and tricyclotetradecane cage ring moieties fused at both ends of two ethylenediamine groups.The average Ni-N distance is 1.904(7) Angstroem.The N-N bite distances are 2.706(6) and 2.698(6) Angstroem for the five-membered chelate rings and 2.703(6) and 2.665(6) Angstroem for the six-membered chelate rings so that the cavity size of the ligand is similar to that of 1,4,7,10-tetraazacyclododecane.Reduction of 2 with Na/Hg gave PF6, which shows an anisotropic axial EPR powder spectrum with g values of g <*> > g <*> .

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Perylene diimide isomers containing a simple sp3-core for non-fullerene-based polymer solar cells

In order to investigate the effect of the geometries of perylene diimide (PDI)-based small molecules, five different isomers were synthesized by using a cyclohexane core as a simple sp3-sigma core. Diaminocylohexane is such an effective core for the systematic development of many kinds of isomers via geometric tuning as well as for reducing the self-aggregation tendency of PDIs. Depending on the anchoring position of the PDI units on the cyclohexane core (ortho-, meta- and para-), isomers exhibited differences in solubility and crystallinity. Among the studied isomers, ortho-substituted t-OCP was found to have a highly twisted molecular structure which minimizes the strong tendency towards crystallization due to individual PDI moieties. The unique geometrical nature of the t-OCP isomer led to the highest power conversion efficiency (PCE = 6.23%) of bulk heterojunction (BHJ) polymer solar cells (PSCs) with a higher short-circuit current density (Jsc) and fill factor (FF). It is mainly ascribed to the formation of a nanophase interpenetrating network with well-balanced carrier mobility in the blend film.

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Catalytic and mechanistic studies into the epoxidation of styrenes using manganese complexes of structurally similar polyamine ligands

Two structurally similar polyamine ligands (7 and 8) have been prepared, which differ only by the presence of either a secondary or tertiary nitrogen donor within their N5 donor set. The ligands, in combination with iron and manganese salts, have been screened for their efficacy as catalysts for the epoxidation of styrene, using both hydrogen peroxide and peracetic acid as oxidants. Clear differences in activity between the two systems were observed, with 7 proving most effective in the presence of MnSO4 with H 2O2, whereas ligand 8 proved to be effective with Mn(OTf)2, MnCl2 and Mn(ClO4)2 using peracetic acid as the oxidant. A Hammett analysis of the initial rate kinetics of the optimal systems, combined with analysis by UV-vis spectroscopy, indicates that the small structural differences in the ligands elicit profound changes in the nature of the active species formed. The Royal Society of Chemistry.

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Using enantioselective dispersive liquid?liquid microextraction for the microseparation of trans-cyclohexane-1,2-diamine enantiomers

A new chiral separation system effective for the enantioselective extraction of racemic trans-cyclohexane-1,2-diamine is presented. Enantioselective dispersive liquid?liquid microextraction has been used for the chiral microseparation of trans-cyclohexane-1,2-diamine, with a chiral azophenolic crown ether being identified as a versatile chiral selector. The influence of various process conditions on the extraction performance was studied experimentally. It was found that the operational selectivity in one extraction step is mainly related to the type and volume of the solvents, chiral selector concentration, extraction time, temperature of sample solution, and pH. At optimum conditions (300?muL of diethyl ether as the extraction solvent 1?mL of methanol as the disperser solvent, with 5?mmol?L?1 chiral selector concentration, pH of the sample equal to 4.5, 30?min extraction time and a temperature of 10?C), the distribution ratio of (R,R)- and (S,S)-trans-cyclohexane-1,2-diamine was 18.3 and 1.8, respectively, while the enantioselectivity value of 10.2 was found at the optimum condition.

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Incorporation of hydrogen-bonding functionalities into the second coordination sphere of iron-based water-oxidation catalysts

Energy storage and conversion schemes based on environmentally benign chemical fuels will require the discovery of faster, cheaper, and more robust catalysts for the oxygenevolution reaction (OER). Although the incorporation of pendant bases into molecular catalysts for hydrogen production and utilization has led to enhanced turnover frequencies, the analogous incorporation of pendant bases into molecular catalysts for water oxidation has received little attention. Herein, the syntheses, structures, and catalytic activities of new iron complexes with pendant bases are reported. Of these new complexes, [Fe(L1)]2+ {L1 = N,N’-dimethyl-N,N’- bis(pyridazin-3-ylmethyl)ethane-1,2-diamine} is the most active catalyst. Initial turnover frequencies of 141 and 24 h-1 were measured by using ceric ammonium nitrate at pH 0.7 and sodium periodate at pH 4.7, respectively. These results suggest that the incorporation of pendant bases into molecular catalysts for water oxidation might be an effective strategy that can be considered in the development of new catalysts for the OER, but will require the careful balance of many factors.

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Chiral discrimination by a binuclear pd complex sensor using 31P{1H} NMR

An axially chiral binuclear mu-hydroxo Pd complex (BPHP) first served as an excellent chiral sensor for discriminating a variety of analytes including amino alcohol, amino amide, amino acid, mandelic acid, diol, diamine, and monoamine by 31P{1H} NMR. A detailed recognition mechanism was proposed based on the single crystal and mass spectrum of Pd-complexes. In general, BPHP sensor, through extracting the acidic hydrogen of an analyte by its Pd-OH group, forms stable diastereomeric complexes with two enantiomers of the analyte giving well distinguishable split 31P{1H} NMR signals for chiral discrimination.

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