- A New Manganese(III) Complex from Bis(5-methylsalicylaldehyde)-3-oxapentane-1,5-diamine: Synthesis, Characterization, Antioxidant Activity and Luminescence
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A Schiff base ligand bis(5-methylsalicylaldehyde)-3-oxapentane-1,5-diamine (H2L) has been prepared. Reaction of the shape-specific designed ligand with MnAc2 afforded a new complex, namely, [Mn2L2Ac2] 1. The ligand and complex 1 were characterized by physic-chemical and spectroscopic methods. The crystal structure of complex 1 has been determined by single-crystal X-ray diffraction. It reveals a centrosymmetric binuclear neutral entity, in which Mn(III) ion is bridged by two ligand L and six-coordinated with the coordination surround of distorted octahedron geometry. The antioxidant activities of the ligand and complex 1 were in vitro determined by superoxide and hydroxyl radical scavenging methods, which indicates that the complex 1 exhibits better scavenging activity of hydroxyl radical and superoxide radical than the ligand. Moreover, under the excitation at room temperature, luminescence studies have been carried out on solution-state samples. The result of their fluorescence properties shows that the strong and characteristic luminescence for the ligand and complex. The complex 1 exhibited intense shift in the fluorescence band compare to the ligand attributed to the coupled effect of the metal and the ligand.
- Wu, Huilu,Wang, Cuiping,Wang, Fei,Peng, Hongping,Zhang, Han,Bai, Yuchen
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- Synthesis, crystal structure, antioxidation and fluorescence of two lanthanide complexes with a noncyclic polyether Schiff base ligand
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Two lanthanide (Sm and La) complexes with the Schiff base ligand bis(3-methoxysalicylidene)-3-oxapentane-1,5-diamine (Bod) have been synthesized and characterized by physico-chemical and spectroscopic methods. [Sm(Bod)(NO3)3] {bis(3-methoxysalicylidene)-3-oxapentane-1,5-diamine samarium(III) trinitrate} (1) is a discrete mononuclear species and [La(Bod)(NO3)3(DMF)]n {bis(3-methoxysalicylidene)-3-oxapentane-1,5-diamine dimethylformamide lanthanum(III) trinitrate}n (2) formed an inorganic coordination polymer. In the two complexes, the metal ions are both ten-coordinate and the geometric structure around the Ln(III) ions can be described as distorted hexadecahedral. An antioxidant assay in vitro shows that complexes 1 and 2 exhibit better scavenging activity than both the ligand and the usual antioxidants on hydroxyl and superoxide radicals. Under excitation at room temperature, a red shift in the fluorescence band of the ligand in the complexes compared with that of the free ligand can be attributed to coordination of the rare earth ions to the ligand. Furthermore, 1 produced characteristic Sm(III) luminescence, which indicates the ligand Bod is a good organic chelator to absorb energy and transfer it to the Sm3+ ion.
- Shi, Xinkui,Mao, Shanshan,Shen, Kesheng,Wu, Huilu,Tang, Xia
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- A convenient preparation of diamino oligoethylene glycols and amino polyethylene glycols
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Diamino oligoethylene glycols and amino polyethylene glycols were prepared in good yields by using the reaction of sodium diformamide with oligoethylene glycol or polyethylene glycol dichlorides or ditosylates followed by hydrolysis using ethanolic hydrochloride.
- Yinglin,Tianbao,Hongwen,Xiao
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- Synthesis and cytotoxic activity of novel 11-methyl-6H-pyrido[4,3-b]carbazole derivatives linked to amine, N-methylurea, and N-methyl-N-nitrosourea moieties with various types of carbamoyl tethers at the C-5 atom
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Thirty-five types of novel pyridocarbazoles (5-(N-alkyl)carbamoyl-11-methyl-6H-pyrido[4,3-b]carbazoles and 5-(N-alkyl)carbamoyl-2,11-dimethyl-6H-pyrido[4,3-b]carbazol-2-ium chloride derivatives), that were conjugated with amine, N-methylurea, and N-methyl-N-nitrosourea moieties through alkyl-, oxyalkyl-, and iminoalkylcarbamoyl linkers, were synthesized by a series of reactions of methyl 11-methyl-6H-pyrido[4,3-b]carbazole-5-carboxylates with polymethylenediamine (n=2–5), p-nitrophenyl N-methylcarbamate, and N-methyl-N-nitrosocarbamate in high yields, and their cytotoxic activities were evaluated against Sarcoma-180, NIH3T3, HeLa S-3, and L1210?cell lines. These compounds exhibited potent cytotoxic activity (IC50=1.6–50?μM) and odd-even alternation effect. 9-Methoxy-2,11-dimethyl-5-((2-(3-methyl-3-nitrosoureido)ethyl)carbamoyl)-6H-pyrido[4,3-b]carbazol-2-ium chloride exhibited the most potent cytotoxic activity (IC50=0.15?μM) and cell selectivity against HeLa S-3. Some of the un-charged 5-(N-alkyl)carbamoyl-6H-pyrido[4,3-b]carbazole derivatives, which were conjugated with the amine and N-methyl-N-nitrosourea moieties through a dimethylene spacer, also exhibited potent cytotoxic activity (IC50=0.43–2.4?μM) and remarkable cell selectivity as well as ellipticine, 9-hydroxyellipticine, and the starting methyl ester of the pyridocarbazole-5-carboxylate (IC50=0.30–2.2?μM).
- Kato, Asako,Nagatsuka, Yusuke,Hiratsuka, Tomokazu,Kiuchi, Satoko,Iwase, Yoko,Okuno, Yuri,Tsukamoto, Tetsuya,Kiran,Sakai, Norio,Konakahara, Takeo
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- Lower ligand denticity leading to improved thermodynamic and kinetic stability of the Gd3+ complex: The strange case of OBETA
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OBETA, OBETA, you bet: Thermodynamic and kinetic measurements show an apparent paradox. The stability of complexes of lanthanide trivalent ions is higher with the heptadentate ligand OBETA (ethylene glycol-bis(2-aminoethyl ether)-N,N,N',N'-tetraacetic aci
- Baranyai, Zsolt,Botta, Mauro,Fekete, Marianna,Giovenzana, Giovanni B.,Negri, Roberto,Tei, Lorenzo,Platas-Iglesias, Carlos
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- Dicopper(II) Complexes of an N6O2 Macrocycle and Seven-co-ordinate Manganese(II), Iron(II), Cobalt(II), Nickel(II), Copper(II), and Zinc(II) Complexes of its N5O2 Open-chain Precursor
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The syntheses via metall-ion (Mg(2+), Ca(2+), or Ba(2+)) template methods followed by transmetallation, of the complexes (ML1)X2 (M=MnII, FeII, CoII, NiII, CuII, or ZnII; X=ClO4(1-) or BPh4(1-)) of the potentially septidentate ligand L1 formed by condensation of 1 mol of 2,6-diacetylpyridine with 2 mol of 3-oxapentane-1,5-diamine is described.The collective evidence of the properties (magnetic and spectroscopic) of the complexes indicates a seven-co-ordinate (pentagonal-bipyramidal) structure.Ring closure, via a transamination mechanism, of L1 in BaL1(ClO4)2 leads to the complex BaL2(ClO4)2*3H2O containing the 24-membered N6O2 macrocyclic ligand L2.The single Ba(2+) in this complex may be replaced by two copper(II) ions to afford the binuclear complex Cu2L2(ClO4)4*H2O which on treatment with imidazole (Him) gives Cu2L2(im)(ClO4)3*H2O containing an imidazolate bridge between the antiferromagnetically coupled metal centres.
- Nelson S. Martin,Knox C. Victor
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- Chemical Promiscuity of Non-Macrocyclic Multidentate Chelating Ligands for Radiometal Ions: H4neunpa-NH2vs H4noneunpa
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A comparative investigation of two structurally related potentially nonadentate chelating ligands, H4neunpa-NH2 and H4noneunpa, has been undertaken to examine the influence of bifunctionalization on their coordination chemistry and metal ion selectivity. Significantly improved synthetic routes for each compound have been developed, employing straightforward high-yielding strategies. Radiolabeling studies with [44Sc]Sc3+, [111In]In3+, [177Lu]Lu3+, and [225Ac]Ac3+ revealed a sharp contrast between the affinity of each chelator for large radiometal ions. H4noneunpa demonstrated highly effective coordination of [177Lu]Lu3+ and [225Ac]Ac3+ achieving quantitative radiochemical yields (>98%) at ligand concentrations of 10-6 M (room temperature (RT), 10 min), with excellent stability when challenged in human serum, while H4neunpa-NH2 was unable to complex either metal ion effectively. Nuclear magnetic resonance (NMR) spectroscopy was employed to explore the coordination chemistry of each chelating ligand with nonradioactive metal ions, spanning a range of ionic radii and coordination numbers. A comprehensive conformational analysis of each metal complex was undertaken using density functional theory (DFT) calculations to explore the coordination geometries and explain the discrepancy in binding characteristics. Theoretical simulations revealed notable differences in the coordination geometry and apparent denticity of each ligand, which together account for the observed selectivity in metal binding and have important implications for the future design of complexes based upon this framework to target large radiometal ion coordination.
- Wharton, Luke,Kurakina, Elena,Radchenko, Valery,Schaffer, Paul,Orvig, Chris
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supporting information
p. 4076 - 4092
(2021/04/07)
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- Electrochemical CO2 Reduction-The Effect of Chalcogenide Exchange in Ni-Isocyclam Complexes
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Among the numerous homogeneous electrochemical CO2 reduction catalysts, [Ni(cyclam)]2+ is known as one of the most potent catalysts. Likewise, [Ni(isocyclam)]2+ was reported to enable electrochemical CO2 conversion but has received significantly less attention. However, for both catalysts, a purposeful substitution of a single nitrogen donor group by chalcogen atoms was never reported. In this work, we report a series of isocyclam-based Ni complexes with {ON3}, {SN3}, {SeN3}, and {N4} moieties and investigated the influence of nitrogen/chalcogen substitution on electrochemical CO2 reduction. While [Ni(isocyclam)]2+ showed the highest selectivity toward CO2 reduction within this series with a Faradaic efficiency of 86% for the generation of CO at an overpotential of-1.20 V and acts as a homogeneous catalyst, the O-and S-containing Ni complexes revealed comparable catalytic activities at ca. 0.3 V milder overpotential but tend to form deposits on the electrode, acting as precursors for a heterogeneous catalysis. Moreover, the heterogeneous species generated from the O-and S-containing complexes enable a catalytic hydride transfer to acetonitrile, resulting in the generation of acetaldehyde. The incorporation of selenium, however, resulted in loss of CO2 reduction activity, mainly leading to hydrogen generation that is also catalyzed by a heterogeneous electrodeposit.
- Apfel, Ulf-Peter,Battistella, Beatrice,Gerschel, Philipp,Ray, Kallol,Siegmund, Daniel
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p. 1497 - 1510
(2020/04/30)
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- Bivalent HIV-1 fusion inhibitors based on peptidomimetics
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Membrane fusion is a valid target for inhibition of HIV-1 replication. A 34-mer fragment peptide (C34), which is contained in the HIV-1 envelope protein gp41, has significant anti-HIV activity. Previously, a dimeric derivative of C34 linked by a disulfide bridge at its C-terminus was found to have more potent anti-HIV activity than the C34 peptide monomer. To date, several peptidomimetic small inhibitors have been reported, but most have lower potency than peptide derivatives related to C34. In the present study we applied this dimerization concept to these peptidomimetic small inhibitors and designed several bivalent peptidomimetic HIV-1 fusion inhibitors. The importance of the length of linkers crosslinking two peptidomimetic compounds was demonstrated and several potent bivalent inhibitors containing tethered peptidomimetics were produced.
- Kobayakawa, Takuya,Ebihara, Kento,Tsuji, Kohei,Kawada, Takuma,Fujino, Masayuki,Honda, Yuzuna,Ohashi, Nami,Murakami, Tsutomu,Tamamura, Hirokazu
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- Synthesis method of 2'-oxydiethylamine and product thereof
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The invention discloses a synthesis method of 2'-oxydiethylamine and the product thereof, and belongs to the field of compound production. The method comprises the steps of using dichlorodiethyl etheras an initial raw material, then carrying out heating reaction on the dichlorodiethyl ether and phthalimide potassium in a first organic solvent at first to generate 2,2'-diphthalimide diethyl ether,carrying out heating reflux reaction on the 2,2'-diphthalimide diethyl ether and hydrazine hydrate in a second organic solvent after purifying the 2,2'-diphthalimide diethyl ether to generate a crudeproduct 2'-oxydiethylamine, and purifying the crude product 2'-oxydiethylamine to obtain the pure product 2'-oxydiethylamine. The product produced through the method is high in yield and high in purity, and the controllability is high; and the purity of the obtained product is greatly improved compared with that of a product obtained through a conventional method.
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(2019/08/12)
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- A novel graphite-like stacking structure in a discrete molecule and its molecular recognition behavior
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A graphite-like stacking structure was nicely reproduced in a discrete molecule that was prepared by 2+2 macrocyclic Schiff base formation. In the crystal structure, two hexabenzocoronene planes are closely stacked with displacement, yielding the intramolecular stacking structure similar to an AB- or ABC-stacking pattern in natural graphite. This molecule showed a recognition ability toward electron-deficient aromatic molecules in solution.
- Akine, Shigehisa,Onuma, Takahiro,Nabeshima, Tatsuya
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supporting information
p. 9369 - 9372
(2018/06/18)
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- Synthesis, Crystal Structure, Fluorescent and Antioxidation Properties of Cerium(III) and Europium(III) Complexes with Bis(3-methoxysalicylidene)-3-oxapentane-1,5-diamine
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Two aliphatic ether Schiff base lanthanide complexes (Ln = Eu, Ce) with bis(3-methoxysalicylidene)-3-oxapentane-1,5-diamine (Bod), were synthesized and characterized by physicochemical and spectroscopic methods. [Eu(Bod)(NO3)3] (1) is a discrete mononuclear species and [Ce(Bod)(NO3)3DMF]∞ (2) exhibits an inorganic coordination polymer. In the two complexes, the metal ions both are ten-coordinated and the geometric structure around the LnIII atom can be described as distorted hexadecahedron. Under excitation at room temperature, the red shift in the fluorescence band of the ligand in the complexes compared with that of the free ligand can be attributed to coordination of the rare earth ions to the ligand. Moreover, the antioxidant activities of the two complexes were investigated. The results demonstrated that the complexes have better scavenging activity than both the ligand and the usual antioxidants on the hydroxyl and superoxide radicals.
- Tang, Xia,Shi, Xinkui,Xu, Yuling,Shen, Kesheng,Mao, Shanshan,Wu, Huilu
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supporting information
p. 379 - 386
(2017/03/21)
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- Specific fluorescence labeling of target proteins by using a ligand-4-azidophthalimide conjugate
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We herein propose a simple affinity-labeling method using a ligand-4-azidophthalimide (AzPI) conjugate. As a proof of concept, we show that two different ligand-AzPI conjugates enabled highly specific fluorescence labeling of their individual target proteins even in crude cell lysates. This method was also applied to label endogenous target proteins inside living cells.
- Chiba, Kosuke,Asanuma, Miwako,Ishikawa, Minoru,Hashimoto, Yuichi,Dodo, Kosuke,Sodeoka, Mikiko,Yamaguchi, Takao
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supporting information
p. 8751 - 8754
(2017/08/10)
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- mellow amination by homogeneous catalysis of the method for the production of primary amines
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The invention relates to a method for producing primary amines by means of the alcohol amination of alcohols with ammonia, with water being eliminated. The method comprises the steps of: (a) a homogenously-catalysed reaction of a reaction mixture which contains at least one alcohol, ammonia, at least one non-polar solvent, and at least one catalyst containing at least one element selected from groups 8, 9 and 10 of the periodic table in the liquid phase, a product mixture (P) thus being obtained; (b) separating the phases of product mixture (P) which was obtained in step (a), if necessary after a reduction in temperature, a reduction in pressure and/or the addition of at least one polar solvent with a miscibility gap in relation to the non-polar solvent, and thus obtaining at least one polar product phase (A) and at least one non-polar phase (B) containing at least one portion of the catalyst that was introduced, with said non-polar phase (B) being separated off, (c) returning at least one portion of the non-polar phase (B) into the reaction in step (a), and (d) separating the amination product from the polar product phase (A). The non-polar solvent introduced in (a) and the catalyst introduced in step (a) are selected such that the catalyst in the non-polar phase (B) becomes enriched.
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Paragraph 0265; 0268
(2016/10/09)
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- METHOD FOR PRODUCING ALKANOL AMINES BY HOMOGENEOUSLY CATALYZED ALCOHOL AMINATION
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PROBLEM TO BE SOLVED: To provide a method for producing alkanol amines by alcohol amination of diols using ammonia under elimination of water. SOLUTION: The invention relates to a method for producing alkanol amines which comprise a primary amino group (-NH2) and a hydroxyl group (-OH), by alcohol amination of diols comprising two hydroxyl groups (-OH) using ammonia under elimination of water. The reaction is homogeneously catalyzed in the presence of at least one complex catalyst which contains at least one element selected from groups 8, 9 and 10 of the periodic table and at least one donor ligand. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPO&INPIT
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Paragraph 0088; 0100
(2016/10/27)
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- The preparation obtained by homogeneous catalysis mellow amination method of the primary amine
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The invention relates to a method for producing primary amines comprising at least one functional group of formula (-CH2-NH2), by alcohol amination of educts which comprise at least one functional group of formula (-CH2-OH), using ammonia, and elimination of water. The homogeneously catalyzed alcohol amination is carried out in the presence of at least one complex catalyst which contains at least one element selected from the groups 8 and 9 of the periodic table and at least one phosphorus donor ligand of general formula (I).
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Paragraph 0207-0208; 0213
(2017/02/28)
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- Synthesis, structure, antioxidation, and DNA-binding studies of a binuclear ytterbium(III) complex with bis(N-salicylidene)-3-oxapentane-1,5-diamine
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A new complex of ytterbium(III) nitrate with bis(N-salicylidene)-3-oxapentane-1,5-diamine (H2L), with the composition Yb2(L)2(NO3)2·2H2O, was synthesized and characterized by physic-chemical and spectroscopic methods. The crystal structure of the ytterbium(III) complex has been determined by single-crystal X-ray diffraction. It reveals a centrosymmetric binuclear neutral entity where Yb(III) metal centers are bridged by two phenoxo oxygen atoms. Electronic absorption titration spectra, ethidium bromide displacement experiments, and viscosity measurements indicate that both the ligand and the Yb(III) complex can bind calf thymus DNA, presumably via a groove binding mechanism. Furthermore, the antioxidant activities of the Yb(III) complex were determined by a superoxide and hydroxyl radical scavenging method in vitro, which indicates that it is a scavenger for OH and O2 - radicals.
- Wu, Huilu,Pan, Guolong,Bai, Yuchen,Wang, Hua,Kong, Jin,Shi, Furong,Zhang, Yanhui,Wang, Xiaoli
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p. 3375 - 3388
(2015/06/08)
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- Powerful Bipodal Anion Transporters Based on Scaffolds That Contain Different Chalcogens
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A new family of bipodal anion transporters based on chalcogen-containing scaffolds has been designed and synthesized. Though structurally related to the well-studied tripodal anionophores, these molecules are simpler with only two anion-binding sites. However, the activities remain high. Anion transport could be facilitated by the new transporter at an exceptionally low loading of transporter/lipid ratio of 1:500000. This impressive efficiency is comparable with the most active one from the tren-based tripodal series. To investigate influences from different scaffolds and substituent groups, lipophilicity, anion-binding property, and transport activity of each molecule were studied. It was found that the bridge atom has a major impact on transport activities mainly as a result of anion-binding differences. The results also suggest that chalcogen can act as a key structural modulator to develop highly effective anion transporters and optimize their activities. Anion transporters based on chalcogen-containing scaffolds have been designed and synthesized. Their lipophilicities, anion binding properties, and transport activities were investigated in detail. The results suggest that chalcogen can act as a key structural modulator to develop highly effective anion transporters and optimize their activities.
- Lang, Chao,Zhang, Xin,Luo, Quan,Dong, Zeyuan,Xu, Jiayun,Liu, Junqiu
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p. 6458 - 6465
(2015/10/19)
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- · Uniform catalyst by using alcohol aminosilicone di-, tri-and a method of manufacturing a polyphenylenepolyamine
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The invention relates to a method for producing primary amines, which contain at least one functional group of the formula (-CH2-NH2) and at least one further primary amino group, by the alcohol amination of reactants, which contain at least one functional group of the formula (-CH2-OH) and at least one further functional group (-X), wherein (-X) is selected from hydroxyl groups and primary amino groups, using ammonia with removal of water, wherein the reaction is carried out in a homogeneously catalyzed manner in the presence of at least one complex catalyst containing at least one element selected from groups 8, 9 and 10 of the periodic table and at least one donor ligand.
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Paragraph 0099; 0108; 0109
(2016/10/09)
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- Synthesis, crystal structure, antioxidation and DNA-binding properties of a dinuclear copper(II) complex with bis(N-salicylidene)-3-oxapentane-1,5-diamine
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A Schiff base bis(N-salicylidene)-3-oxapentane-1,5-diamine (H2L) and its Cu(II) complex, [Cu2(L)2]·CHCl3, have been synthesized and characterized by physicochemical and spectroscopic methods. Single-crystal X-ray analysis revealed that the complex is a centrosymmetric binuclear neutral entity, in which Cu(II) is a five-coordinate in a distorted trigonal bipyramidal geometry. The DNA-binding properties of the free ligand and the complex have been investigated by electronic absorption, fluorescence, and viscosity measurements. The results suggest that the H2L and the complex to DNA via the intercalation mode and the binding affinity of the complex were higher than that of the H2L. The intrinsic binding constants Kb of the ligand and the complex are 2.2 × 104 and 2.7 × 104 M-1, respectively. Antioxidant assay in vitro shows the Cu(II) complex possesses significant antioxidant activities and better scavenging activity than the H2L and other antioxidants.
- Wu, Huilu,Bai, Yuchen,Zhang, Yanhui,Li, Zhen,Wu, Mingchang,Chen, Chengyong,Zhang, Jiawen
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p. 3054 - 3066
(2015/10/20)
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- Preparation, structure, DNA-binding properties, and antioxidant activities of a homodinuclear erbium(III) complex with a pentadentate Schiff base ligand
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An erbium (III) complex of a pentadentate Schiff base ligand [(NO 3)Er(μ-L)2Er(NO3)].2H2O [H 2L=bis(N-salicylidene)-3- oxapentane-1,5-diamine] has been synthesised, characterised and its structure confirmed by X-ray crystallography. H2L and the Er(III) complex both bind to DNA via a groove binding mode, and the Er(III) complex binds to DNA more strongly than H2L. The complex shows strong scavenging effects for hydroxyl radicals (OH·) and superoxide radicals (O2-·).
- Wu, Huilu,Pan, Guolong,Bai, Yuchen,Wang, Hua,Kong, Jin,Shi, Furong,Zhang, Yanhui,Wang, Xiaoli
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p. 211 - 217
(2014/05/06)
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- Two Lanthanide(III) Complexes based on the Schiff Base N,N'- Bis(salicylidene)-1,5-diamino-3-oxapentane: Synthesis, Characterization, DNA-binding Properties, and Antioxidation
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The Schiff base N,N'-bis(salicylidene)-1,5-diamino-3-oxapentane (H 2L) and its lanthanide(III) complexes, PrL(NO3)(DMF) (H2O) (1) and Ho2L2(NO3) 2·2H2O (2), were synth
- Wu, Huilu,Bai, Yuchen,Zhang, Yanhui,Pan, Guolong,Kong, Jin,Shi, Furong,Wang, Xiaoli
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p. 2062 - 2071,10
(2014/12/09)
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- Synthesis, crystal structure, DNA-binding properties and antioxidant activities of a lutetium(III) complex with the bis(N-salicylidene)-3-oxapentane- 1,5-diamine ligand
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A Schiff base ligand bis(N-salicylidene)-3-oxapentane-1,5-diamine (H 2L) and its lutetium(III) complex, with composition Lu 2(L)2 (NO3)2, were synthesized and characterized by physico-chemical and spectroscopic methods. The crystal structure of the Lu(III) complex has been determined by single-crystal X-ray diffraction. It reveals a centrosymmetric binuclear neutral entity where Lu(III) metal centers are bridged by two phenoxo oxygen atoms. The DNA-binding properties of the Lu(III) complex were investigated by spectrophotometric methods and viscosity measurements, and the results suggest that the Lu(III) complex binds to DNA via a groove binding mode. Additionally, the antioxidant activity of the Lu(III) complex was determined by the superoxide and hydroxyl radical scavenging methods in vitro, which indicate that it is a scavenger for OH and O2- radicals.
- Pan, Guolong,Bai, Yuchen,Wang, Hua,Kong, Jin,Shi, Furong,Zhang, Yanhui,Wang, Xiaoli,Wu, Huilu
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p. 257 - 266
(2013/06/27)
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- Further studies on bis-charged tetraazacyclophanes as potent inhibitors of small conductance Ca2+-activated K+ channels
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Previously, quinolinium-based tetraazacyclophanes, such as UCL 1684 and UCL 1848, have been shown to be extraordinarily sensitive to changes in chemical structure (especially to the size of the cyclophane system) with respect to activity as potent non-peptidic blockers of the small conductance Ca 2+-activated K+ ion channels (SKCa). The present work has sought to optimize the structure of the linking chains in UCL 1848. We report the synthesis and SKCa channel-blocking activity of 29 analogues of UCL 1848 in which the central CH2 of UCL 1848 is replaced by other groups X or Y = O, S, CF2, CO, CHOH, CC, CHCH, CHMe to explore whether subtle changes in bond length or flexibility can improve potency still further. The possibility of improving potency by introducing ring substituents has also been explored by synthesizing and testing 25 analogues of UCL 1684 and UCL 1848 with substituents (NO2, NH2, CF 3, F, Cl, CH3, OCH3, OCF3, OH) in the 5, 6 or 7 positions of the aminoquinolinium rings. As in our earlier work, each compound was assayed for inhibition of the afterhyperpolarization (AHP) in rat sympathetic neurons, an action mediated by the SK3 subtype of the SK Ca channel. One of the new compounds (39, R7 = Cl, UCL 2053) is twice as potent as UCL 1848 and UCL 1684: seven are comparable in activity.
- Yang, Donglai,Arifhodzic, Lejla,Ganellin, C. Robin,Jenkinson, Donald H.
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supporting information
p. 907 - 923
(2013/07/27)
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- A Schiff base bis(N-salicylidene)-3-oxapentane-1,5-diamine and its yttrium(III) complex: Synthesis, crystal structure, DNA-binding properties, and antioxidant activities
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A Schiff base bis(N-salicylidene)-3-oxapentane-1,5-diamine (H2L) and its yttrium(III) (Y(III)) complex, Y2L2(NO 3)2?2H2O, have been synthesized and characterized by physico-chemical and spectroscopic methods. The crystal structure of the Y(III) complex has been determined by single-crystal X-ray diffraction, revealing a centrosymmetric binuclear neutral entity where Y(III) centers are bridged by two phenoxo oxygens. The DNA-binding properties of the Schiff base H2L and the Y(III) complex were investigated by spectrophotometric methods and viscosity measurements. The results suggest that ligand H2L and Y(III) complex both bind to DNA via groove binding, and the Y(III) complex binds to DNA more strongly than H2L. The antioxidant activity of the Y(III) complex was determined by superoxide and hydroxyl radical-scavenging method in vitro, which indicates that Y(III) complex scavenges OH? and O2 radicals.
- Wu, Huilu,Pan, Guolong,Bai, Yuchen,Wang, Hua,Kong, Jin,Shi, Furong,Zhang, Yanhui,Wang, Xiaoli
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p. 2634 - 2646
(2014/02/14)
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- PROCESS FOR THE PREPARATION OF PRIMARY AMINES BY HOMOGENEOUSLY CATALYZED ALCOHOL AMINATION
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Preparing a primary amine by alcohol amination of alcohol with ammonia and elimination of water includes reacting, in a homogeneously catalyzed reaction, a mixture of alcohol, ammonia, nonpolar solvent, and catalyst, in a liquid phase, to obtain a product mixture. The process then includes phase separating the product mixture into a polar product phase and a nonpolar product phase, and separating off the nonpolar product phase. At least some of the nonpolar phase returns to the homogenously catalyzed reaction. The process further includes separating off amination product from the polar product phase. At least some of the catalyst is in the nonpolar phase, and the catalyst accumulates in the nonpolar phase.
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(2012/09/22)
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- PROCESS FOR PREPARING DI-, TRI- AND POLYAMINES BY HOMOGENEOUSLY CATALYZED ALCOHOL AMINATION
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Process for preparing primary amines which have at least one functional group of the formula (—CH2—NH2) and at least one further primary amino group by alcohol amination of starting materials having at least one functional group of the formula (—CH2—OH) and at least one further functional group (—X), where (—X) is selected from among hydroxyl groups and primary amino groups, by means of ammonia with elimination of water, wherein the reaction is carried out homogeneously catalyzed in the presence of at least one complex catalyst comprising at least one element selected from groups 8, 9 and 10 of the Periodic Table and also at least one donor ligand.
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Page/Page column 12; 14
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- PROCESS FOR PREPARING ALKANOLAMINES BY HOMOGENEOUSLY CATALYZED ALCOHOL AMINATION
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Process for preparing alkanolamines which have a primary amino group (—NH2) and a hydroxyl group (—OH) by alcohol amination of diols having two hydroxyl groups (—OH) by means of ammonia with elimination of water, wherein the reaction is carried out homogeneously catalyzed in the presence of at least one complex catalyst comprising at least one element selected from groups 8, 9 and 10 of the Periodic Table and also at least one donor ligand.
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Page/Page column 13-14; 17
(2012/09/22)
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- PROCESS FOR THE PREPARATION OF PRIMARY AMINES BY HOMOGENEOUSLY CATALYZED ALCOHOL AMINATION
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Process for the preparation of primary amines which have at least one functional group of the formula (—CH2—NH2) by alcohol amination of starting materials which have at least one functional group of the formula (—CH2—OH), with ammonia, with the elimination of water, where the alcohol amination is carried out under homogeneous catalysis in the presence of at least one complex catalyst which comprises at least one element selected from groups 8 and 9 of the Periodic Table of the Elements, and also at least one phosphorus donor ligand of the general formula (I).
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Page/Page column 10; 12
(2012/09/22)
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- MACROCYCLIC HOPO CHELATORS
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The present invention provides a novel class of macrocyclic compounds as well as complexes formed between a metal (e.g., lanthanide) ion and the compounds of the invention. Preferred complexes exhibit high stability as well as high quantum yields of lanthanide ion luminescence in aqueous media without the need for secondary activating agents. Preferred compounds comprise hydroxypyridinonyl moieties within their macrocyclic structure and are characterized by surprisingly low, non-specific binding to a variety of polypeptides such as antibodies and proteins as well as high kinetic stability.
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Page/Page column 50
(2011/04/14)
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- PROSTAGLANDIN TRANSPORTER INHIBITORS AND USES THEREOF
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Disclosed are compounds for inhibiting prostaglandin transporter (PGT) activity, pharmaceuticals compositions including the compounds, and methods of treating subjects using the compounds.
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Page/Page column 57
(2011/04/24)
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- Synthesis of a series of N6-substituted adenosines with activity against trypanosomatid parasites
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The involvement of purine salvage in the accumulation of current trypanocidal drugs is important for the treatment of African sleeping sickness. The substrate specificity of essential nucleoside transporters is therefore of physiological and pharmacological interest. With the intention to contribute to the knowledge in the field, a series of 16 adenosine derivatives with substituents in N6-position were prepared in order to evaluate their potential to inhibit Trypanosoma brucei spp. in vitro. An unmodified ribose moiety was selected to conserve key molecular recognition motifs of the arsenal of integral membrane proteins expressed in large numbers on the protozoan plasma membrane. Two of the new compounds prepared using a polymer-assisted acylation protocol showed antitrypanosomal activities in the single digit micromolar concentration range.
- Link, Andreas,Heidler, Philipp,Kaiser, Marcel,Brun, Reto
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experimental part
p. 3665 - 3671
(2009/12/04)
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- LUMINESCENT 1-HYDROXY-2-PYRIDINONE CHELATES OF LANTHANIDES
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The present invention provides luminescent complexes between a lanthanide ion and an organic ligand which contains 1,2-hydroxypyridinone units. The complexes of the invention are stable in aqueous solutions and are useful as molecular probes, for example in medical diagnostics and bioanalytical assay systems. The invention also provides methods of using the complexes of the invention.
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Page/Page column 63
(2008/06/13)
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- Direct synthesis of di-heteroatom containing cyclic organic compounds
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The present invention provides for the simplified, direct synthesis of di-heteroatom containing cyclic organic compounds by forming an aqueous mixture of material of the formula 1 wherein X and Y are heteroatoms which may be the same or different and X is selected from the group consisting of O, S and N, and both Y's are the same and are selected from the group consisting of O, S and N, and R1 through R8 are the same or different and are selected from the group consisting of H, C1 to C10 alkyl radicals, C1 to C10 aryl radicals, C1 to C10 alkyl aryl radicals, and z is zero when X and Y are O or S, and z is 1 when X and Y are N, and water at a mole ratio of water to material of formula I in the range of about 10:1 to about 0.001:1 and heating the mixture to a temperature in the range of about 250° C. to about 350° C. under autogeneous pressure for a time of from about 0.5 to 10 hours. Trace amounts of liquid, solid or gaseous acid can be present to further accelerate dehydration, dehydrosulfurization or deamination and cyclization.
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Page/Page column 5
(2008/06/13)
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- Processes for the preparation of aminoethers
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A process for preparing aminoethers, particularly bis[2-(N,N-dialkylamino)alkyl]ethers, which comprises contacting a carboxylated aminoether with a metal oxide catalyst under conditions effective to produce the aminoether. Many of these aminoethers are useful as catalysts in the production of polyurethanes, especially cellular polyurethanes.
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- Perhydrotriquinacenic hosts. 2. Synthesis and complexation properties of speleands of C3symmetry
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The synthesis and complexation properties of four spela0eands (13-16) derived from triol 4 and the chiral C3 concave cap 3, linked to the cyclic aza-oxa macrocycle 2 by means of ester-amide bridges, are described.
- Almansa, Carmen,Moyano, Albert,Serratosa, Felix
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p. 1497 - 1506
(2007/10/02)
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- Host-Guest Complexation. 38. Cryptahemispherands and Their Complexes
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Syntheses and crystal structures are reported for a new class of hosts, their complexes, and their precursors.The cryptahemispherands 5-8 are composed of molecular modules that are half spherand 1 and half cryptand 3.They were synthesized by the reactions of diacid chloride 20 with cyclic diamines 21-23 to produce diamides 13-16, reduction of which gave the desired hosts 5-8.These diamines were best purified, stored, and handled through their respective hydroborane complexes, 9-12.Hosts 6 and 7 are diastereomeric, as are diamides 14 and 15 and hydroborane complexes 10 and 11.Diamines 6 and 7 equilibrate rapidly at 25 deg C probably by ring inversion of the methoxyl groups to give a 5:1 ratio of 6 over 7.Diamides 14 and 15 equilibrate readily at 90 deg C to give only 14 in detectable amounts.Hydroborane complexes 10 and 11 do not equilibrate at 90 deg C.Cryptahemispherands 5, 6 and 8 formed a variety of complexes with the alkali metal cations, diamides 14 and 16 exhibited a low level of binding power, and hydroborane complexes 10 and 12 had no detectable affinity for the alkali metal cations.Hemispherand 17 was synthesized for comparison purposes.Crystal structures were determined for the isomeric diamides 14 and 15, for hydroborane complex 9, and for alkali cation complexes 5.NaB(Ph)4, 6.KSCN, 8.NaSCN, 8.KSCN, and 8.CsClO4.The trisanisyl modules of all eight compounds possess the same preorganized conformation, with the unshared electron pairs of the three methoxyl groups turned inward and the methyl groups outward.The potential cavities of 9, 14, and 15 are filled inward-turned hydrogens of the ethylene bridges.In the alkali metal ion complexes, the unshared electron pairs of the heteroatoms are all turned inward toward the quest metal ion.The use of CPK molecular models in predicting the structures of complexes is evaluated.
- Cram, Donald J.,Ho, Siew Peng,Knobler, Carolyn B.,Maverick, Emily,Trueblood, Kenneth N.
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p. 2989 - 2998
(2007/10/02)
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- Synthesis of +(1.1.1)>X- Cryptates Assisted by Intramolecular Hydrogen Bonding
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Condensation of diazacoronand and diethylene glycol bis(methanesulfonate)as well as with its alkylsubstituted derivatives in the presence of 1 molar equiv of BuLi or KH gives the corresponding +(1.1.1)>X- cryptates in 31-43percent yields.Experimental results indicate that in the intermediate monosubstituted diazacoronand, the NH hydrogen plays a templating role, thus favoring the bicyclic ring closure by intramolecular hydrogen bonding.Similar base-promoted condensations of and diazacoronands with triethylene glycol bis(methanesulfonates) afford and cryptates in 20-35percent yields.
- Anelli, Pier Lucio,Montanari, Fernando,Quici, Silvio
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p. 3453 - 3457
(2007/10/02)
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- Preparation of amines by the reduction of imines with phosphorous acid
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This invention relates to the preparation of amines by the reduction of imines with phosphorous acid, preferably under basic conditions.
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- Process of preparing hexahydropyrimidines
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This invention relates to hexahydropyrimidines (HHP) of the formula STR1 where R' is a substituted group and R is hydrogen or a substituted group; the process of preparing and the uses therefor, particularly as deterioration inhibitors in hydrocarbon fuels.
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- PECULIARITIES OF THE REACTION OF N,N'-SUBSTITUTED DIPHTHALIMIDES WITH AMINES
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Macrocyclic phthalic acid diamides were obtained by the reaction of N,N'-substituted diphthalimides with polyoxyethylenediamines, while the corresponding tetraamides were obtained with primary aliphatic amines.It is shown that the reaction is a thermodynamically controlled process.
- Anikin, V. F.,Ganin, E. V.,Rozynov, B. V.,Zakharova, R. M.,Kamalov, G. L.
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p. 193 - 196
(2007/10/02)
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- Macroheterocycles. III. Synthesis, properties, and tautomeric transformations of macrocyclic thioureas
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Macrocyclic thioureas of the and types, where R=CH2(CH2OCH2)nCH2 and (CH2)m (n=1, 2, 3, m=8), were obtained for the first time by the reaction of diamines with carbon bisulfide.The UV, IR, and PMR spectra of the compounds were studied.It was shown that they exist in the thione form in the crystalline state and in protic solvents.Thione - thiol isomerization is observed in nonpolar solvents.
- Bogatskii, A.V.,Luk'yanenko, N. G.,Kirichenko, T. I.
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p. 1124 - 1129
(2007/10/02)
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- Complexes of macrocyclic compounds
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Novel macrocyclic (monocyclic and bicyclic) compounds having nitrogen bridgehead atoms and having in the hydrocarbon bridging chains at least two additional hetero atoms selected from the group consisting of sulfur, oxygen, and nitrogen, when admixed with a compatible cation-donor compound form stable cation-containing macrocyclic complexes which, in turn, can be conveniently dissociated by addition of acid or a quaternizing agent. The novel macrocyclics are valuable for use in the same way and for the same purposes as chelating agents.
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- Novel bisulfate and sulfate salts of bis(2-aminoethyl) ether and methods of preparation
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The title compounds correspond to formulas O--CH2 CH2 NH3≈)2.2HSO4? and )--CH2 CH2 NH3≈)2 SO4?. They are prepared by (A) reacting by contacting HOCH2 CH2 NH3≈ HSO4? with ≈ NH3 CH2 CH2 O--SO3? in the presence of a catalytic amount of sulfuric acid at a temperature greater than about 140° C, thereby forming a reaction product comprising O--CH2 CH2 NH3≈)2. 2HSO4? ; and (B) reacting by contacting the reaction product of step (A) or O--CH2 CH2 NH3≈)2 . 2HSO4? with a methanol solution of HOCH2 CH2 NH2, thereby forming O--CH2 CH2 NH3≈)2 SO4? as a solid precipitate. The latter compound is extremely useful as a chemical intermediate in forming bis(2-aminoethyl) ether.
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- Amine bisulfites
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This invention relates to the amine bisulfites which are useful as a combination corrosion inhibitor/oxygen scavenger. This is illustrated by heterocyclic amine bisulfites such as pyridine bisulfites.
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- Monocyclic macrocyclic compounds and complexes thereof
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Novel monocyclic macrocyclic compounds having nitrogen bridgehead atoms and having in the hydrocarbon bridging chains at least two additional hetero atoms selected from the group consisting of sulfur, oxygen, and nitrogen, when admixed with a compatible cation-donor compound form stable cation-containing macrocyclic complexes which, in turn, can be conveniently dissociated by addition of acid or a quaternizing agent. The novel macrocyclics are valuable for use in the same way and for the same purposes as chelating agents.
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