- Palladium complexes bearing an N-heterocyclic carbene–sulfonamide ligand for cooligomerization of ethylene and polar monomers
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Herein, we report the synthesis of palladium complexes bearing an N-heterocyclic carbene (NHC)-sulfonamide bidentate ligand and their application in ethylene oligomerization and ethylene/polar monomer cooligomerization. These catalysts could smoothly catalyze ethylene oligomerization and ethylene/methyl acrylate cooligomerization albeit the performance was lower compared to that of a NHC–phenoxide catalyst.
- Tao, Wenjie,Wang, Xiaoming,Ito, Shingo,Nozaki, Kyoko
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- Primaquine synergises the activity of chloroquine against chloroquine-resistant P. falciparum
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In recent years, resistance to the antimalarial drug, chloroquine, has become widespread. It is, therefore, imperative to find compounds that could replace chloroquine or work synergistically with this drug to overcome chloroquine resistance. We have examined the interaction between chloroquine, a 4-aminoquinoline, and a number of 8-aminoquinolines, including primaquine, a drug that is widely used to treat Plasmodium vivax infections. We find that primaquine is a potent synergiser of the activity of chloroquine against chloroquine-resistant Plasmodium falciparum. Analysis of matched transfectants expressing mutant and wild-type alleles of the P. falciparum chloroquine resistance transporter (PfCRT) indicate that primaquine exerts its activity by blocking PfCRT, and thus enhancing chloroquine accumulation. Our data suggest that a novel formulation of two antimalarial drugs already licensed for use in humans could be used to treat chloroquine-resistant parasites.
- Bray, Patrick G.,Deed, Samantha,Fox, Emma,Kalkanidis, Martha,Mungthin, Mathirut,Deady, Leslie W.,Tilley, Leann
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- Long-Chain Alkyl-Substituted 1,10-Phenanthrolines as Surfactant Ligands for Transition-Metal Ions. 1. Synthesis of 4- and 4,7-n-Undecyl-Substituted 1,10-Phenanthrolines
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A convenient synthesis for 4- and 7-n-undecyl-1,10-phenanthrolines, based on a modified Doebner-von Miller reaction, is described for the following 1,10-phenanthrolines: 4-n-undecyl, 4,7-di-n-undecyl, 2-methyl-4-n-undecyl, 2,9-dimethyl-4-n-undecyl, and 2-methyl-7-n-undecyl.
- Lund, Gary K.,Holt, Smith L.
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- Planar-locked Ru-PNN catalysts in 1-phenylethanol dehydrogenation
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Ru-PNN pincer catalysts of the general form [{PNN}Ru(H)(Cl)(CO)] can dehydrogenate alcohols through inner- and outer-sphere mechanisms, but determining the favored path is challenging. To address this challenge, the following planar-locked quinoline-based PNN ligands, which cannot form key inner-sphere transition states and intermediates, were synthesized: 2-((ditertbutylphosphaneyl)methyl)-N,N-diethylquinolin-8-amine (QNPtBu), 2-((diisopropylphosphaneyl)methyl)-N,N-diethyl-quinolin-8-amine (QNPiPr), and 2-((diphenylphosphaneyl)-methyl)-N,N-diethylquinolin-8-amine (QNPPh). In addition to the quinoline-derived ligands, we also prepared the isoquinoline PNN ligand N-((1-((ditert-butylphosphaneyl)methyl)isoquinolin-3-yl)methyl)-N-ethylethanamine (IsoQNP) and two known picoline- and lutidine-derived ligands 2-((ditert-butylphosphaneyl)-methyl)pyridine (PicP) and 2-((ditert-butylphosphaneyl)methyl)-6-methylpyridine (LutP). These six ligands were coordinated to Ru(II) ions to prepare six new complexes of the general formulation [{L}Ru(H)(Cl)(CO)] analogous to Milstein’s PNN catalyst precursor (1PyCl). The X-ray structural, NMR, UV-vis, and FTIR spectroscopic properties of the new complexes are similar to parent complex 1PyCl and were used in catalytic 1-phenylethanol acceptor-less and transfer dehydrogenation. The comparative results demonstrate that 1Py outperforms the other catalysts. DFT reaction profiles were computed for 1Py and the planar-locked catalysts. The results suggest that 1Py has access to a lower-energy inner-sphere path, whereas the planar-locked catalysts can only proceed through a high-energy outer-sphere mechanism and may even get trapped in unreactive alkoxide sinks.
- Fanara, Paul M.,MacMillan, Samantha N.,Lacy, David C.
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- Development of Improved Amidoquinoline Polyolefin Catalysts with Ultrahigh Molecular Weight Capacity
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A new synthetic route to amidoquinoline olefin polymerization catalysts has been developed involving significantly less expensive and more readily available starting materials. The new methodology was used to prepare N-mesityl-2-methylquinolin-8-amine, which in turn was converted into trialkyl complexes of Hf, Zr, and Ti. The new complexes were characterized by elemental analysis, 1D and 2D NMR spectroscopy, and X-ray crystallography. A batch reactor ethylene/1-octene copolymerization evaluation at 140 C showed that the new Hf congener outperformed a series of previously reported molecular olefin polymerization catalysts. In particular, the new Hf catalyst exhibits excellent activity and a remarkable capacity to produce ultrahigh molecular weight copolymers at elevated reaction temperatures. (Chemical Presented).
- Fontaine, Philip P.,Ueligger, Steve,Klosin, Jerzy,Hazari, Amaruka,Daller, Joe,Hou, Jianbo
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- Synthesis of mono-and dialkylsubstituted 1,10-Phenanthrolines
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Starting from o-anisidine, alkylated 8-hydroxyquinolines 2 and 8-aminoquinolines 3 were obtained. From the latter, dialkylsubstituted 1,10-phenanthrolines 5 have been prepared in good yields. Reaction of unsubstituted 8-aminoquinoline under the same conditions, yielded monoalkylated 1,10-phenanthrolines 4.
- Belser, Peter,Bernhard, Stefan,Guerig, Urs
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- Convenient syntheses and preliminary photophysical properties of novel 8-aminoquinoline appended diaza-18-crown-6 ligands
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Novel 7,16-bis(8-amino-2-quinolinylmethyl)- and 7,16-bis(8-amino-7-quinolinylmethyl)-diaza-18-crown-6 ligands (12 and 16) have been synthesized by reductive amination of 8-(di-tert-butoxycarbonyl)amino-2-quinolinecarboxaldehyde (followed by removal of the Boc protecting groups) or 8-amino-7-quinolinecarboxaldehyde with diaza-18-crown-6 using triacetoxyborohydride (NaBH(OAc)3) as the reducing agent. The crystal structure of ligand 16 is also given. The absorption spectra of 12 and 16 are dominated by two intense bands at 250±5 and 238±1 nm which are blue shifted upon addition of alkaline earth and heavy metal ions in acetonitrile. In addition, intensities of the fluorescence bands of 12 and 16 are reduced in the presence of metal ions.
- Xue, Guoping,Bradshaw, Jerald S,Dalley, N.Kent,Savage, Paul B,Krakowiak, Krzysztof E,Izatt, Reed M,Prodi, Luca,Montalti, Marco,Zaccheroni, Nelsi
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- Substitution effect on the one- and two-photon sensitivity of DMAQ "caging" groups
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The systematic SAR study of a "caging" group showed a strong influence of the position of the donor dimethylamino group on the efficiency of photolysis of the DMAQ (2-hydroxymethylene-(N,N-dimethylamino)quinoline) caged acetate under one-photon near-UV or two-photon near-IR excitation. Photorelease of l-glutamate by the most efficient 8-DMAQ derivative strongly and efficiently activated glutamate receptors, generating large, fast rising responses similar to those elicited by glutamate photoreleased from the widely used MNI-caged glutamate.
- Petit, Morgane,Tran, Christine,Roger, Thomas,Gallavardin, Thibault,Dhimane, Hamid,Palma-Cerda, Francisco,Blanchard-Desce, Mireille,Acher, Francine C.,Ogden, David,Dalko, Peter I.
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- Stepwise construction of polysubstituted phenanthroline-based glutamate pockets for lanthanide complexation
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A multi-functionalized ligand, based on a glutamic acid skeleton, bearing phenanthroline carboxylic units as chromophores and chelating arms has been designed. A base-assisted bis N-alkylation of dimethyl glutamate hydrochloride with the pivotal 2-carbomethoxy-4-methoxy-9-bromomethyl-1,10-phenanthroline building block, followed by a saponification step, provided the target ligand as its tetrahydrochloride salt. The spectroscopic properties of the ligand and its lanthanide(III) complexes were investigated in aqueous 0.01 M TRIS/HCl buffer at pH 7.0. The europium(III) complex was highly luminescent, exhibiting a quantum yield of 6% despite the presence of ca. one molecule of water in the first coordination sphere, whereas the terbium(III) complex was only weakly luminescent. Georg Thieme Verlag Stuttgart.
- Ziessel, Raymond,Weibel, Nicolas,Charbonniere, Loic J.
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- Continuous and Selective Hydrogenation of Heterocyclic Nitroaromatics in a Micropacked Bed Reactor
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The hydrogenation of heterocyclic nitroaromatics is of great importance in the pharmaceutical industry for the synthesis of key intermediates. However, high selectivity is difficult to achieve in conventional batch reactors owing to severe back mixing and poor mass transfer performance, resulting in the high requirement for subsequent separation processes. In this work, a continuous flow system based on a micropacked bed reactor is developed for the selective hydrogenation of heterocyclic nitroaromatics and the reductions of 5-nitroisoquinoline to 5-aminoisoquinoline and 5-amino-1,2,3,4-tetrahydroisoquinoline are selected as the model reactions. With the optimal reaction conditions, maximal yields of 99.9% (5-aminoisoquinoline) and 99.3% (5-amino-1,2,3,4-tetrahydroisoquinoline) are obtained successfully. Moreover, this system exhibits remarkable performance for the selective hydrogenation of relevant heterocyclic nitroaromatics with all yields beyond the level of 97.5%. The continuous flow system enables efficient hydrogenation of heterocyclic nitroaromatics and remarkable selectivity of target products with shorter reaction time and safer operation compared with batch reactors.
- Chen, Xingkun,Duan, Xiaonan,Wang, Xuepeng,Zhang, Jisong
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p. 2100 - 2109
(2021/09/08)
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- NaI/PPh3-Mediated Photochemical Reduction and Amination of Nitroarenes
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A mild transition-metal- and photosensitizer-free photoredox system based on the combination of NaI and PPh3 was found to enable highly selective reduction of nitroarenes. This protocol tolerates a broad range of reducible functional groups such as halogen (Cl, Br, and even I), aldehyde, ketone, carboxyl, and cyano. Moreover, the photoredox catalysis with NaI and stoichiometric PPh3 provides also an alternative entry to Cadogan-type reductive amination when o-nitrobiarenes were used.
- Qu, Zhonghua,Chen, Xing,Zhong, Shuai,Deng, Guo-Jun,Huang, Huawen
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supporting information
p. 5349 - 5353
(2021/07/21)
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- Method for reducing aromatic nitro into arylamine
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The invention relates to a method for reducing aromatic nitro to arylamine. The method comprises the following steps: (1) taking an aromatic nitro compound as a raw material, water as a hydrogen source, a palladium compound, cheap and easy to obtain, as a catalyst and tetrahydroxydiboron as an additive to reduce nitro to obtain a product; (2) taking the aromatic nitro compound as the raw material, a copper salt, cheap and easy to obtain, as the catalyst, the tetrahydroxydiboron as the additive to reduce the nitro to obtain a product; and (3) taking the aromatic nitro compound as the raw material, water as the hydrogen source, and the tetrahydroxydiboron as the additive, without needing a metal catalyst, to reduce the nitro to obtain a product. A preparation method for the arylamine, which is provided by the invention, is mild in reaction condition, low in costs, environment-friendly, high in yield, and suitable for industrial production.
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Paragraph 0201-0204; 0253-0256; 0293-0296
(2020/07/15)
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- HETEROCYCLIC CARBOXYLIC ACID AMIDE LIGAND AND APPLICATIONS THEREOF IN COPPER CATALYZED COUPLING REACTION OF ARYL HALOGENO SUBSTITUTE
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Provided are a heterocyclic carboxylic acid amide ligand and applications thereof in a copper catalyzed coupling reaction. Specifically, provided are uses of a compound represented by formula (I), definitions of radical groups being described in the specifications. The compound represented by formula (I) can be used as the ligand in the copper catalyzed coupling reaction of the aryl halogeno substitute, and is used or catalyzing the coupling reaction for forming the aryl halogeno substitute having C—N, C—O, C—S and other bonds.
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Paragraph 0266-0267
(2019/05/15)
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- Oxalic amide ligands, and uses thereof in copper-catalyzed coupling reaction of aryl halides
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The present invention provides oxalic amide ligands and uses thereof in copper-catalyzed coupling reaction of aryl halides. Specifically, the present invention provides a use of a compound represented by formula I, wherein definitions of each group are described in the specification. The compound represented by formula I can be used as a ligand in copper-catalyzed coupling reaction of aryl halides for the formation of C—N, C—O and C—S bonds.
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Page/Page column 89-90
(2020/01/09)
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- Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant
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A photoreductive protocol utilizing [Ru(bpy)3]2+ photocatalyst, blue light LEDs, and ascorbic acid (AscH2) has been developed to reduce nitro N-heteroaryls to the corresponding anilines. Based on experimental and computational results and previous studies, we propose that the reaction proceeds via proton-coupled electron transfer between AscH2, photocatalyst, and the nitro N-heteroaryl. The method offers a green catalytic procedure to reduce, e.g., 4-/8-nitroquinolines to the corresponding aminoquinolines, substructures present in important antimalarial drugs.
- Todorov, Aleksandar R.,Aikonen, Santeri,Muuronen, Mikko,Helaja, Juho
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supporting information
p. 3764 - 3768
(2019/05/24)
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- Cu-catalyzed reduction of azaarenes and nitroaromatics with diboronic acid as reductant
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A ligand-free copper-catalyzed reduction of azaarenes with diboronic acid as reductant in an aprotic solvent under mild conditions has been developed. Most interestingly, the nitroazaarenes could be reduced exclusively to give the corresponding amines without touching the azaarene moieties. Furthermore, the reductive amination of aromatic nitro compounds and aromatic aldehydes has also been realized. A series of hydrogenated azaarenes and secondary amines were obtained with good functional group tolerance.
- Pi, Danwei,Zhou, Haifeng,Zhou, Yanmei,Liu, Qixing,He, Renke,Shen, Guanshuo,Uozumi, Yasuhiro
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p. 2121 - 2129
(2018/03/23)
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- Preparation of Tetradentate Copper Chelators as Potential Anti-Alzheimer Agents
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The uncontrolled redox activity of metal ions, especially copper, in the brains of patients with Alzheimer's disease (AD) should be considered the origin of intense oxidative damage to neurons in the AD brain. To obtain low-molecular-weight copper chelators that act as tetradentate ligands, we designed new compounds based on an 8-aminoquinoline motif with a lateral chain attached at the 2-position of the aromatic ring. Some of these new ligands, termed TDMQ for TetraDentate MonoQuinolines, are specific for copper chelation. Full characterization of these ligands is reported, as well as their affinities for CuII, and their capacities to inhibit oxidative stress induced by copper–amyloids activated by a reductant. Such metal ligands can be considered as potential anti-AD agents, as they should be able to regulate the homeostasis of copper in brain tissue.
- Zhang, Weixin,Huang, Daya,Huang, Meijie,Huang, Ju,Wang, Dean,Liu, Xingguo,Nguyen, Michel,Vendier, Laure,Mazères, Serge,Robert, Anne,Liu, Yan,Meunier, Bernard
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p. 684 - 704
(2018/02/28)
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- Metal-free Reduction of Nitro Aromatics to Amines with B 2 (OH) 4 /H 2 O
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A metal-free reduction of nitro aromatics mediated by diboronic acid with water as both the hydrogen donor and solvent under mild conditions has been developed. A series of aromatic amines were obtained with good functional group tolerance and in good yields.
- Chen, Danyi,Zhou, Yanmei,Zhou, Haifeng,Liu, Sensheng,Liu, Qixing,Zhang, Kaili,Uozumi, Yasuhiro
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supporting information
p. 1765 - 1768
(2018/06/26)
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- Water as a hydrogen source in palladium-catalyzed reduction and reductive amination of nitroarenes mediated by diboronic acid
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An unprecedented palladium-catalyzed chemoselective reduction and reductive amination of nitroarenes with water as a hydrogen source mediated by diboronic acid have been discovered. A series of aryl amines containing various reducible functional groups were obtained in good to excellent yields.
- Zhou, Yanmei,Zhou, Haifeng,Liu, Sensheng,Pi, Danwei,Shen, Guanshuo
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p. 3898 - 3904
(2017/06/13)
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- Discovery of N-(Naphthalen-1-yl)-N′-alkyl Oxalamide Ligands Enables Cu-Catalyzed Aryl Amination with High Turnovers
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A class of N-(naphthalen-1-yl)-N′-alkyl oxalamides have been proven to be powerful ligands, making a coupling reaction of (hetero)aryl iodides with primary amines proceed at 50 °C with only 0.01 mol % of Cu2O and ligand as well as a coupling reaction of (hetero)aryl bromides with primary amines and ammonia at 80 °C with only 0.1 mol % of Cu2O and ligand. A wide range of coupling partners work well under these conditions, thereby providing an easy to operate method for preparing (hetero)aryl amines.
- Gao, Jie,Bhunia, Subhajit,Wang, Kailiang,Gan, Lu,Xia, Shanghua,Ma, Dawei
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supporting information
p. 2809 - 2812
(2017/06/07)
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- Synthesis of fluorine-containing 1,10-phenanthrolines using mild versions of Skraup and Doebner-von Miller reactions
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A versatile route for the synthesis of new 1,10-phenanthroline derivatives with fluorine-containing groups is described. Skraup reactions were performed with yields of 19 up to 48% and overall yields of 5 up to 13% based on different fluorinated anilines as starting materials. Ten formerly unknown derivatives were synthesized and characterized by NMR spectroscopy (1H,13C,19F), ESI mass spectrometry and elemental analysis.
- Lüdtke, Carsten,Haupt, Axel,Wozniak, Martin,Kulak, Nora
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- Color filter comprising Yellow Dye and Display Device using the same
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The present invention relates to a color filter comprising a yellow dye which is composed of a compound represented by chemical formula 1 (in the chemical formula 1, R1 to R8 are respectively made of hydrogen or an alkyl group having 1-20 carbon atoms). The present invention further relates to a display device using the color filter.(AA) Penetration rate(%)(BB) Wavelength(nm)(CC) No baking(DD) Baking at 180anddeg;C(EE) Baking at 200anddeg;C(FF) Baking at 230anddeg;CCOPYRIGHT KIPO 2016
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Paragraph 0033; 0034; 0035
(2016/10/20)
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- Color filter comprising Yellow Dye and Method of manufacturing the same and Display Device using the same
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The present invention relates to a color filter comprising a yellow dye, a manufacturing method thereof, and a display device using the same. The yellow dye comprises a compound represented by chemical formula 1. In the chemical formula 1, R1 to R5 are independently composed of hydrogen or a C1-C20 alkyl group, and R6 to R13 are independently composed of a halogen group.(CC) No baking(BB) Wavelength(nm)(AA) Absorbing rate(FF) Baking at 230anddeg;C(EE) Baking at 200anddeg;C(DD) Baking at 180anddeg;CCOPYRIGHT KIPO 2015
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Paragraph 0028-0030
(2017/01/05)
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- Assembly of Primary (Hetero)Arylamines via CuI/Oxalic Diamide-Catalyzed Coupling of Aryl Chlorides and Ammonia
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A general and practical catalytic system for aryl amination of aryl chlorides with aqueous or gaseous ammonia has been developed, with CuI as the catalyst and bisaryl oxalic diamides as the ligands. The reaction proceeds at 105-120°C to provide a diverse set of primary (hetero)aryl amines in high yields with various functional groups.
- Fan, Mengyang,Zhou, Wei,Jiang, Yongwen,Ma, Dawei
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supporting information
p. 5934 - 5937
(2015/12/11)
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- Copper(II)-coordinated α-Azophenols: Effect of the metal-ion geometry on phenoxyl/phenolate oxidation potential and reactivity
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Two copper(II) complexes were synthesized from tridentate ligands involving a (Nquinoline,Nazo,Ophenol) donor set. The copper(II) ion is tetracoordinate with a chloride ion occupying the fourth position of the coordination sphere. Both X-ray diffraction and electron paramagnetic resonance (EPR) spectroscopy reveal that the copper(II) ion geometry is square planar in 1. In contrast, significant tetrahedral distortions are observed in 2, as a result of the steric clash between the hydrogen atoms of the methyl substituent of the quinoline group and the chloride ion. Cyclic voltammetry curves of 1 and 2 in CH2Cl2 display a reversible oxidation wave at E1/2 = 0.59 V and 0.56 V versus ferrocenium/ferrocene, respectively, which was assigned to the phenoxyl/phenolate redox couple. Compounds 1+ and 2+ were generated and characterized by UV/Vis and EPR spectroscopy. Their reactivity with benzyl alcohol was investigated by kinetic measurements. Tetrahedral distortion at the metal ion in a copper(II) complex containing tridentate ligands with a (Nquinoline,Nazo,Ophenol) donor set is tuned by the α-quinoline substituent. The CuII-phenoxyl radical species oxidizes benzyl alcohol at rate constants that are essentially independent of the distortion at the metal center.
- Kochem, Amélie,Carrillo, Alexandre,Philouze, Christian,Van Gastel, Maurice,Du Moulinet D'Hardemare, Amaury,Thomas, Fabrice
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supporting information
p. 4263 - 4267
(2015/03/30)
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- Direct amination of phenols under metal-free conditions
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Herein, we disclose the metal-free synthesis of arylamines via the direct amination of phenols using aminating reagents. This reaction procedure uses easy accessible aminating reagents and provides a versatile synthetic route to a broad range of arylamines with various functionalities in good to excellent yield. By using a two-step route of amination and oxidative coupling reaction, we synthesized three naturally occurring carbazole alkaloids: murrayafoline A, mukonine, and clausenine from two commercially available phenols. Georg Thieme Verlag Stuttgart · New York.
- Yu, Jianzhong,Wang, Yongtao,Zhang, Peizhi,Wu, Jun
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supporting information
p. 1448 - 1454
(2013/07/26)
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- Novel Sulfonaminoquinoline Hepcidin Antagonists
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The present invention relates to novel hepcidin antagonists, pharmaceutical compositions comprising them and the use thereof as medicaments for the use in the treatment of iron metabolism disorders, such as, in particular, iron deficiency diseases and anemias, in particular anemias in connection with chronic inflammatory diseases.
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Page/Page column 126
(2012/09/05)
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- Novel guanidine-quinoline hybrid ligands and the application of their zinc complexes in lactide polymerisation
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The syntheses of the three new guanidine-quinoline hybrid ligands TMGmqu, DMEGmqu and TMGtbqu are reported. Zinc chlorido and triflato complexes with these ligands were obtained and structurally characterised by X-ray crystallography. In the chlorido complexes the zinc atom is coordinated by two chlorido ligands and the bidentate guanidine ligand in a distorted tetrahedron. Using zinc triflate, tetrahedral bis(chelate) complexes are formed, and the triflate anions serve only for charge compensation. All reported complexes show activity in the polymerisation of rac-lactide, with the chlorido complexes only showing a poor activity. With the bis(chelate) triflato complexes a high polymerisation activity with a slight heterotactic bias was observed. Kinetic studies reveal a firstorder chain growth reaction for the lactide polymerisation with all complexes.
- Dos Santos Vieira, Ines,Herres-Pawlis, Sonja
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experimental part
p. 320 - 330
(2012/07/14)
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- NOVEL NITROGEN-CONTAINING ORGANIC COMPOUNDS USABLE AS CATALYTIC COMPOSITION PRECURSORS
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The present invention describes novel nitrogen-containing organic compounds obtained by reacting a compound X of substituted pyridine type comprising at least one ketone function with a compound Y belonging to the aminoquinoleine family and derivatives thereof. Said organic compounds can be used as precursors in a catalytic composition.
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Page/Page column 6
(2011/02/15)
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- Synthesis of substituted 8-aminoquinolines and phenanthrolines through a Povarov approach
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The synthesis of 8-aminoquinolines and 1,10-phenanthrolines with substituents in α of the nitrogen has been performed through an inverse-demanding aza-Diels-Alder (Povarov reaction) in the fluoroalcohols TFE or HFIP. This path involves simple starting materials: 1,2-phenylenediamines, enol ethers and aldehydes.
- De, Kavita,Legros, Julien,Crousse, Benoit,Chandrasekaran, Srinivasan,Bonnet-Delpon, Daniele
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supporting information; experimental part
p. 347 - 350
(2011/02/26)
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- Chromofluorescent indicator for intracellular Zn2+/Hg 2+ dynamic exchange
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(Chemical Equation Presented) (Figure Presented) The fluorescence of NABQ increases remarkably in the presence of Zn2+ and is quenched by Hg2+. As shown by confocal imaging, NABQ-Zn2+ can penetrate cells, where the bound Zn2+ is exchanged for Hg 2+. This results in the concomitant export of Hg2+ from the cells, showing that NABQ can act as a Zn2+ carrier and as a Hg2+ extracting agent in living cells.
- Lee, Jeong Won,Jung, Hyo Sung,Kwon, Pil Seung,Kim, Jong Wan,Bartsch, Richard A.,Kim, Youngmee,Kim, Sung-Jin,Kim, Jong Seung
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supporting information; scheme or table
p. 3801 - 3804
(2009/07/01)
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- Reactivity of yttrium quinoline-imine-phenoxide complexes towards interand intramolecular alkyl nucleophilic attacks
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Yttrium(III) chloride complexes [YCl2(NNOH)] (1H) and [YCl2(NNOMe)] (1Me) {NNOH = 2-tert-butyl-6-(quinolin-8-yliminomethyl) phenoxide; NNOMe = 2-tert-butyl-6-[(2-methylquinolin-8-ylimino)methyl]phenoxide} were synthesized by treating a thf solution of YCl3 at room temperature with the NNOH-H and NNOMe-H ligands {NNOH-H = 2-tert-butyl-6-(quinolin-8-yliminomethyl)phenol; NNOMe-H = 2-tert-butyl-6-[(2-methylquinolin-8-ylimino)methyl]phenol}, which were previously deprotonated with potassium tert-butoxide or thallium ethoxide. Surprisingly, reaction of 1H with the Grignard reagent MeMgBr to prepare the corresponding dialkyl derivative led to the formation of the tetranuclear magnesium dimer [Mg2BrCl{NN(Me)OH}(thf)] 2 {NN(Me)OH = 2-tert-butyl-6-[1-(quinolin-8-ylamido)ethyl] phenoxide} (2), whose structure was determined by single-crystal X-ray diffraction. By reacting the neutral ligand NNOH-H with Y(CH 2SiMe3)3·2thf in toluene at low temperature the alkyl complex [Y(CH2SiMe3){NN(CH 2SiMe3)O}(thf)] {NN(CH2Si-Me3)O = 2-tert-butyl-6-[1-(quinolin-8-ylamido)-2-trimethylsilanylethyl] phenoxide} (3) was isolated. The supposed reaction mechanism leading to the formation of 3 was simulated by using the PM6 Hamiltonian. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Paolucci, Gino,Bortoluzzi, Marco,Bertolasi, Valerio
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experimental part
p. 4126 - 4132
(2009/02/07)
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- Tri-substituted triazoles as potent non-nucleoside inhibitors of the HIV-1 reverse transcriptase
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A new series of 1,2,4-triazoles was synthesized and tested against several NNRTI-resistant HIV-1 isolates. Several of these compounds exhibited potent antiviral activities against efavirenz- and nevirapine-resistant viruses, containing K103N and/or Y181C mutations or Y188L mutation. Triazoles were first synthesized from commercially available substituted phenylthiosemicarbazides, then from isothiocyanates, and later by condensing the desired substituted anilines with thiosemicarbazones.
- De La Rosa, Martha,Kim, Hong Woo,Gunic, Esmir,Jenket, Cheryl,Boyle, Uyen,Koh, Yung-hyo,Korboukh, Ilia,Allan, Matthew,Zhang, Weijian,Chen, Huanming,Xu, Wen,Nilar, Shahul,Yao, Nanhua,Hamatake, Robert,Lang, Stanley A.,Hong, Zhi,Zhang, Zhijun,Girardet, Jean-Luc
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p. 4444 - 4449
(2007/10/03)
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- Preparation of some new intercalating europium(III) sensitizers
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The synthesis of phenanthridinium salts linked to a chelating phenanthroline-2,9-dicarboxylic acid group, as in 1 and 2, is described.These derivatives behave as useful probes for the identification of DNA single strands in a new homogeneous assay.
- Mullins, Stephen T.,Sammes, Peter G.,West, Richard M.,Yahioglu, Gokhan
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- Substituted 8-sulfonamidoquinolines
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Certain sulfonamidoquinolines and metal complexes thereof both of which are soluble in essentially water-immiscible organic solvents. The sulfonamidoquinolines have the structural formula STR1 where the R, R1 and R2 groups and m and n are as defined in the specification and claims hereof. Solutions of the sulfonamidoquinolines and the metal complexes thereof in essentially water-immiscible organic solvents.
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