- A novel axially palladium(II)-Schiff base complex substituted silicon(IV) phthalocyanine: Synthesis, characterization, photophysicochemical properties and photodynamic antimicrobial chemotherapy activity against Staphylococcus aureus
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In this study, a novel silicon(IV) phthalocyanine is reported for the first time as a phthalocyanine derivative bearing axially a palladium(II)-Schiff base complex. The photophysical and photochemical properties of the new Si(IV)Pc, such as absorption, fluorescence, singlet oxygen quantum yields, triplet state quantum yields and exited state lifetimes were measured in DMSO. The new silicon phthalocyanine displayed very low fluorescence, showing efficient intersystem crossing resulting in high triplet and high singlet oxygen quantum yields in DMSO. When compared with the unsubstituted SiPcCl2, the singlet oxygen quantum yield value (ΦΔ = 0.47) in relation to the triplet quantum yield (ΦT = 0.82), which is an important determinant for PDT applications, increased. The photodynamic antimicrobial chemotherapy activity (PACT) of new Si(IV)Pc towards Staphylococcus aureus was determined in comparison to the unsubstituted SiPcCl2. The results of the photodynamic antimicrobial effect study demonstrated that the Pd(II) complex substituted SiPc (5) possesses excellent photodynamic activity with a reduction percentage value of 99.94% and a log red value of 3.26.
- Sen, Pinar,Nyokong, Tebello
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- Copper ion-selective fluorescent sensor based on the inner filter effect using a spiropyran derivative
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A highly selective copper(II) ion fluorescent sensor has been designed based on the UV-visible absorption of a spiropyran derivative coupled with the use of a metal porphyrin operative on the fluorescence inner filter effect. Spiropyrans, which combine the characteristics of metal binding and signal transduction, have been widely utilized in cationic ion recognition by UV-visible spectroscopy. In the present work, the viability of converting the absorption signal of the spiropyran molecule into a fluorescence signal was explored. On account of overlap of the absorption band of the spiropyran (λabs = 547 nm) in the presence of copper ion with the Q-band of an added fluorophore, zinc meso-tetraphenylporphyrin (λabs = 556 nm), the effective light absorbed by the porphyrin and concomitantly the emitted light intensity vary as a result of varying absorption of the spiropyran via fluorescence inner filter effect. The metal binding characteristic of the spiropyran presents an excellent selectivity for copper ion in comparison with several other heavy or transition metal ions. Since the changes in the absorbance of the absorber translate into exponential changes in fluorescence of the fluorophore, the novelty of the present device is that the analytical signal is more sensitive over that of the absorptiometry or that of the fluorometry using one single dye. To realize a practical fluorescent sensor, both the absorber and fluorophore were immobilized in a plasticized poly(vinyl chloride) membrane, and the sensing characteristics of the membrane for copper ion were investigated. The sensor is useful for measuring Cu2+ at concentrations ranging from 7.5 × 10-7 to 3.6 × 10 -5 M with a detection limit of 1.5 × 10-7 M. The sensor is chemically reversible, the fluorescence was switched off by immersing the membrane in copper ion solution and switched on by washing it with EDTA solution.
- Shao, Na,Zhang, Ying,Cheung, SinMan,Yang, RongHua,Chan, WingHong,Mo, Tain,Li, KeAn,Liu, Feng
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- Zwitterionic macrocyclic metal sulfate extractants containing 3-dialkylaminomethylsalicylaldimine units
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10,25-Di-tert-alkyl-14,21-dimethyl-3,6,14,21-tetraazatricyclo[21.3.1.18, 12]octacosa-1(27),2,6,8,10,12(28),23,25-octaene-27,28-diol macrocycles form Ni(II) and Cu(II) complexes in which the metal cation and the sulfate anion are bound in separated sites in a zwitterionic form of the ligand. The nonyl-substituted macrocycle shows a higher affinity for SO42- and a lower binding strength for Cu2+ than open chain analogues, the pH-dependences for which fall in ranges which allow loading of CuSO4 at pH ≈4 and easy stripping to recycle the ligand. X-Ray structure determinations of the Cu(II) and Ni(II) sulfate complexes of the tert-butyl substituted ligand suggest that the de-tuning of M2+-binding results from a distortion from planarity of the "salen" N2O22- donor set imposed by the incorporation of the hexamethylene strap in the ligand and reveal that the sulfate is bound as a hydrate in a 2:2:2:2, ligand-M2+-SO42--H2O, assembly.
- Plieger, Paul G.,Tasker, Peter A.,Galbraith, Stuart G.
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- Dual-functional probe based on rhodamine for sequential Cu2+ and ATP detection in vivo
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A rhodamine-based fluorescent probe for Cu2+ and ATP has been designed. The fluorescence intensity/absorbance was significantly enhanced upon the addition of Cu2+ owning to the opening of the spiro-ring of rhodamine, which quickly returned to the original level due to the reconstruction of the probe by the reacting with ATP. Cu2+/ATP-induced fluorescent intensity/aborbance changes showed a good linear relationship with the concentration of Cu2+/ATP in the range of 2–20 μM/0–10 μM with a detection limit of 0.1 μM/1.0 μM. The proposed method is simple in design and fast in operation, and is suitable for the reversible monitoring of Cu2+ and ATP in bioanalytical applications.
- Jin, Xilang,Gao, Jingkai,Xie, Pu,Yu, Mengchen,Wang, Ting,Zhou, Hongwei,Ma, Aijie,Wang, Qian,Leng, Xin,Zhang, Xianghan
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- Structure-Based Design of Potent and Orally Active Isoindolinone Inhibitors of MDM2-p53 Protein-Protein Interaction
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Inhibition of murine double minute 2 (MDM2)-p53 protein-protein interaction with small molecules has been shown to reactivate p53 and inhibit tumor growth. Here, we describe rational, structure-guided, design of novel isoindolinone-based MDM2 inhibitors. MDM2 X-ray crystallography, quantum mechanics ligand-based design, and metabolite identification all contributed toward the discovery of potent in vitro and in vivo inhibitors of the MDM2-p53 interaction with representative compounds inducing cytostasis in an SJSA-1 osteosarcoma xenograft model following once-daily oral administration.
- Chessari, Gianni,Hardcastle, Ian R.,Ahn, Jong Sook,Anil, Burcu,Anscombe, Elizabeth,Bawn, Ruth H.,Bevan, Luke D.,Blackburn, Timothy J.,Buck, Ildiko,Cano, Celine,Carbain, Benoit,Castro, Juan,Cons, Ben,Cully, Sarah J.,Endicott, Jane A.,Fazal, Lynsey,Golding, Bernard T.,Griffin, Roger J.,Haggerty, Karen,Harnor, Suzannah J.,Hearn, Keisha,Hobson, Stephen,Holvey, Rhian S.,Howard, Steven,Jennings, Claire E.,Johnson, Christopher N.,Lunec, John,Miller, Duncan C.,Newell, David R.,Noble, Martin E. M.,Reeks, Judith,Revill, Charlotte H.,Riedinger, Christiane,St. Denis, Jeffrey D.,Tamanini, Emiliano,Thomas, Huw,Thompson, Neil T.,Vinkovi?, Mladen,Wedge, Stephen R.,Williams, Pamela A.,Wilsher, Nicola E.,Zhang, Bian,Zhao, Yan
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supporting information
p. 4071 - 4088
(2021/05/04)
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- Enantioselective Hydroboration of Ketones Catalyzed by Rare-Earth-Metal Complexes Supported with Phenoxy-Functionalized TsDPEN Ligands
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Six novel chiral rare-earth-metal complexes bearing the phenoxy-functionalized TsDPEN ligand H3L1 (H3L1 = N-((1R,2R)-2-((3,5-di-Tert-butyl-2-hydroxybenzyl)amino)-1,2-diphenylethyl)-4-methylbenzenesulfonamide) were synthesized successfully and well characterized. The solid-state structures of four tetranuclear rare-earth-metal complexes [RE2L13]2 (RE = Nd (1), Sm (2), Eu (3), Gd (4)) and the dual-core yttrium complex Y2L13 (5) were determined by X-ray diffraction, respectively. The structure of lanthanum complex 6 was speculated by the 1H DOSY spectroscopy in THF-d8 together with DFT calculations. Complexes 1-5 were employed to catalyze the enantioselective hydroboration of ketones and α,β-unsaturated ketones using pinacolborane (HBpin) as a reductant, and complex 1 gave better outcomes in comparison to the others. The corresponding secondary alcohols were obtained in excellent yields and moderate ee values. The same results were also achieved using the combined catalyst system of the neodymium amide Nd[N(SiMe3)2]3 with the phenoxy-functionalized TsDPEN ligand H3L1 in a 1:1.5 molar ratio.
- Yu, Qishun,Lu, Chengrong,Zhao, Bei
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supporting information
p. 2529 - 2537
(2021/07/28)
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- Unprecedented reductive cyclisation of salophen ligands to tetrahydroquinoxalines during metal complex formation
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The synthesis of novel tetrahydroquinoxalines by a metal induced one-electron reductive cyclisation of salophen ligands was found to occur when a salophen ligand was treated with chromium(ii) chloride or decamethylcobaltocene.
- Dowsett, Mark R.,Lamb, Katie J.,North, Michael,Parker, Rachel R.,Whitwood, Adrian C.
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supporting information
p. 4844 - 4847
(2020/05/13)
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- Development of a Cofilin Inhibitor for the Treatment of Hemorrhagic Brain Injury-Induced Neuroinflammation
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Compounds and methods for inhibiting cofilin activity or reducing total cofilin, improving motor deficits, attenuating LPS-induced microglial activation and inflammation, reducing microglial migration and proliferation, reducing TNF-α, reducing NF-κB, and improving motor deficits in a subject are described.
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Paragraph 0035; 0074; 0075
(2020/12/08)
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- Phosphine-Catalyzed [3+2] Annulation of β-Sulfonamido-Substituted Enones with Sulfamate-Derived Cyclic Imines
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Phosphine-catalyzed [3+2] annulation of β-sulfonamido-substituted enones and sulfamate-derived cyclic imines has been developed, giving a series of imidazoline derivatives in moderate to excellent yields with good to excellent diastereoselectivities. A scale-up reaction worked well under mild reaction conditions. A possible mechanism was proposed on the basis of the results obtained.
- Shi, Wangyu,Zhou, Leijie,Mao, Biming,Wang, Qijun,Wang, Chang,Zhang, Cheng,Li, Xuefeng,Xiao, Yumei,Guo, Hongchao
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supporting information
p. 679 - 685
(2019/01/24)
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- Synthesis of Monofunctionalized Calix[5]arenes
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Seven OH-free and O -permethylated monofunctionalized calix[5]arenes carrying either additional methyl or tert -butyl groups are prepared following fragment condensation protocols. This strategy proves to be superior to previous approaches. Calix[5]arenes with free OH groups all adopt a cone conformation stabilized by a seam of hydrogen bonds at the lower rim. Post-condensation modifications, i.e., methylation of phenolic OH groups or functional group interconversions can also be achieved. Bulky tert -butyl groups are also found to stabilize the cone conformations of O -methylated compounds. These compounds offer versatile functional groups that make these concave molecules interesting building blocks for the synthesis of more sophisticated molecular architectures.
- Ingenfeld, Bj?rn,Straub, Steffen,Fr?mbgen, Christopher,Lützen, Arne
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p. 676 - 684
(2017/11/16)
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- Efficient microwave-assisted regioselective one pot direct: Ortho -formylation of phenol derivatives in the presence of nanocrystalline MgO as a solid base catalyst under solvent-free conditions
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In this research, at first nanocrystalline MgO was prepared and then the solvent-free reactions of phenol derivatives with paraformaldehyde in the presence of the obtained nanocrystalline MgO as a new catalyst under microwave irradiation were investigated. In this reaction, ortho-hydroxyaromatic aldehydes were yielded as products. This method seems to be comparable with other reported methods due to its high yield and regioselectivity. The significant features of this method are short reaction times, high yields, and easy and quick isolation of the products.
- Naeimi, Hossein,Zakerzadeh, Elham
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p. 4590 - 4595
(2018/03/21)
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- Enantioselective Construction of Tetrahydroquinazoline Motifs via Palladium-Catalyzed [4 + 2] Cycloaddition of Vinyl Benzoxazinones with Sulfamate-Derived Cyclic Imines
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A palladium-catalyzed enantioselective [4 + 2] cycloaddition reaction of vinyl benzoxazinones with sulfamate-derived cyclic imines is described, affording the tetrahydroquinazolines bearing several functional rings in high yields (up to 99% yield) with good to excellent diastereoselectivities and excellent enantioselectivities (up to 96% ee). This reaction represents the first Pd-catalyzed asymmetric decarboxylative cycloaddition of vinyl benzoxazinones with imines.
- Wang, Chang,Li, Yan,Wu, Yang,Wang, Qijun,Shi, Wangyu,Yuan, Chunhao,Zhou, Leijie,Xiao, Yumei,Guo, Hongchao
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supporting information
p. 2880 - 2883
(2018/05/29)
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- Synthesis characterization and cytotoxicity studies of platinum(II) complexes with reduced amino pyridine schiff base and its derivatives as ligands
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A series of reduced amino pyridine Schiff base platinum(II) complexes were prepared as potential anticancer drugs, and characterized by NMR, IR spectroscopy, elemental analysis, and molar conductivity. UV and CD results showed the binding mode between these compounds and salmon sperm DNA may be intercalation. The cytotoxicity of these complexes was validated against A549, Hela, and MCF-7 cell lines by MTT assay. Some complexes exhibited better cytotoxic activity than cisplatin against Hela and MCF-7 cell lines.
- Li, Li-Jun,Yan, Qin-Qin,Liu, Guo-Jun,Yuan, Zhen,Lv, Zhen-Hua,Fu, Bin,Han, Yan-Jun,Du, Jian-Long
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p. 1081 - 1089
(2017/05/29)
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- Polynuclear Enantiopure Salen-Mesoionic Carbene Hybrid Complexes
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Salen ligands and mesoionic carbene (MIC) ligands constitute important ligand classes in homogeneous catalysis. In this article we describe the first integration of a salen moiety and MIC donors in the same catalyst entity. Homo- and heterometallic polynuclear metal complexes could be selectively prepared by first installing a metal center (Ni(II), Pd(II)) in the N2O2 salen sphere followed by metalation of the mesoionic carbenes (Ag(I), Pd(II)). The silver complexes could be used for transmetalations to form Au(III) complexes. Several complexes showed catalytic activity in the 1,4-addition of an oxindole to a nitroolefin.
- Schmid, Juliane,Frey, Wolfgang,Peters, René
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p. 4313 - 4324
(2017/11/20)
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- Salicylaldehyde Hydrazones: Buttressing of Outer-Sphere Hydrogen-Bonding and Copper Extraction Properties
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Salicylaldehyde hydrazones are weaker copper extractants than their oxime derivatives, which are used in hydrometallurgical processes to recover ～20% of the world's copper. Their strength, based on the extraction equilibrium constant Ke, can be increased by nearly three orders of magnitude by incorporating electron-withdrawing or hydrogen-bond acceptor groups (X) ortho to the phenolic OH group of the salicylaldehyde unit. Density functional theory calculations suggest that the effects of the 3-X substituents arise from a combination of their influence on the acidity of the phenol in the pH-dependent equilibrium, Cu2++2Lorg→[Cu(L-H)2]org+2H+, and on their ability to 'buttress' interligand hydrogen bonding by interacting with the hydrazone N-H donor group. X-ray crystal structure determination and computed structures indicate that in both the solid state and the gas phase, coordinated hydrazone groups are less planar than coordinated oximes and this has an adverse effect on intramolecular hydrogen-bond formation to the neighbouring phenolate oxygen atoms.
- Roach, Benjamin D.,Lin, Tai,Bauer, Heiko,Forgan, Ross S.,Parsons, Simon,Rogers, David M.,White, Fraser J.,Tasker, Peter A.
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p. 556 - 565
(2017/05/09)
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- Phosphine-Catalyzed [4 + 2] Annulation of Allenoate with Sulfamate-Derived Cyclic Imines: A Reaction Mode Involving γ′-Carbon of α-Substituted Allenoate
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A phosphine-catalyzed [4 + 2] cycloaddition of cyclic α-substituted allenoates with sulfamate-derived cyclic imines has been reported. Using dibenzylphenylphosphine as the nucleophilic catalyst, the reaction worked efficiently to yield various fused multicyclic heterocyclic compounds in high yields with excellent diastereoselectivities. It undergoes a new reaction mode involving γ′-carbon of α-substituted allenoate.
- Mao, Biming,Shi, Wangyu,Liao, Jianning,Liu, Honglei,Zhang, Cheng,Guo, Hongchao
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supporting information
p. 6340 - 6343
(2017/12/08)
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- Olefin polymerization and copolymerization by complexes bearing [ONNO]-Type salan ligands: Effect of ligand structure and metal type (titanium, zirconium, and vanadium)
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A series of novel titanium(IV) complexes bearing tetradentate [ONNO] salan type ligands: [Ti{2,2′-(OC6H3-5-t-Bu) 2-NHRNH}Cl2] (Lig1TiCl2: R = C 2H4; Lig2TiCl2: R = C 4H8; Lig3TiCl2: R = C 6H12) and [Ti{2,2′-(OC6H 2-3,5-di-t-Bu)2-NHC6H12NH}Cl 2] (Lig4TiCl2) were synthesized and used in the (co)polymerization of olefins. Vanadium and zirconium complexes: [M{2,2′-(OC6H3-3,5-di-t-Bu)2-NHC 6H12NH}Cl2] (Lig4VCl2: M = V; Lig4ZrCl2: M = Zr) were also synthesized for comparative investigations. All the complexes turned out active in 1-octene polymerization after activation by MAO and/or Al(i-Bu)3/[Ph 3C][B(C6F5)4]. The catalytic performance of titanium complexes was strictly dependent on their structures and it improves for the increasing length of the aliphatic linkage between nitrogen atoms (Lig1TiCl2 2TiCl2 3TiCl2) and declines after adding additional tert-Bu group on the aromatic rings (Lig3TiCl2 4TiCl2). The activity of all titanium complexes in ethylene polymerization was moderate and the properties of polyethylene was dependent on the ligand structure, cocatalyst type, and reaction conditions. The Et2AlCl-activated complexes gave polymers with lover molecular weights and bimodal distribution, whereas ultra-high molecular weight PE (up to 3588 kg mol-1) and narrow MWD was formed for MAO as a cocatalyst. Vanadium complex yielded PE with the highest productivity (1925.3 kg mol v-1), with high molecular weight (1986 kg mol -1) and with very narrow molecular weight distribution (1.5). Copolymerization tests showed that titanium complexes yielded ethylene/1-octene copolymers, whereas vanadium catalysts produced product mixtures.
- Bialek, Marzena,Pochwala, Monika,Spaleniak, Grzegorz
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p. 2111 - 2123
(2014/07/08)
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- A family of enantiopure FeIII4 single molecule magnets: Fine tuning of energy barrier by remote substituent
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A new family of enantiopure star-shaped FeIII4 single-molecule magnets (SMMs) with the general formula [Fe4(L K)6] (H2L = (R or S)-2-((2-hydroxy-1- phenylethylimino methyl)phenol); K = H (1), Cl (2), Br (3), I (4), and t-Bu (5)), were structurally and magnetically characterized. Complex 1 was reported in our previous paper (Chem. Commun., 2011, 47, 8049-8051). Detailed magnetic measurements and a systematic magneto-structural correlation study revealed that the SMM properties of this series of compounds can be finely tuned by the remote substituent of the ligands. Although the change in the coordination environment of the central Fe3+ ions is very small, the properties of SMM behavior are changed considerably. All five complexes display frequency dependence of the ac susceptibility. However, the χ′′ac peaks of complexes 2 and 5 cannot be observed down to 0.5 K. The fitted anisotropy energy barriers (Ueff) of complexes 1, 3, and 4 were 5.9, 7.1, and 11.0 K, respectively. Moreover, the hysteresis loops of these three complexes can be also observed around 0.5 K. Magneto-structural correlation analyses revealed that the coordination symmetry of the central Fe3+ ion and the intermolecular interaction are two key factors affecting the SMM properties. Deviation to a trigonal prism coordination environment and the existence of intermolecular interactions between neighboring clusters may both reduce the anisotropy energy barriers. This journal is the Partner Organisations 2014.
- Zhu, Yuan-Yuan,Cui, Chang,Qian, Kang,Yin, Ji,Wang, Bing-Wu,Wang, Zhe-Ming,Gao, Song
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supporting information
p. 11897 - 11907
(2014/08/05)
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- Phenylene-diimine-capped conjugate of lower rim 1,3-Calix[4]arene as molecular receptor for Mg2+ via arm conformational changes followed by aggregation and mimicking the species by molecular mechanics
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A phenylene-diimine-capped conjugate of lower rim 1,3-calix[4]arene (L) was synthesized, characterized, and shown to selectively bind to Mg2+ using its capped arms. This results in a selective recognition of Mg 2+ through eliciting fluorescence enhancement of ～70 fold with a detection limit of 40 ± 5 ppb. However, in the presence of blood serum, the lowest detection limit is 209 ± 10 ppb (0.2 μM). The binding of Mg2+ to L is authenticated by absorption and 1H NMR data. The Jobs plot derived on the basis of the absorption data showed 1:1 stoichiometry between the receptor and Mg2+. The 1:1 species was further confirmed through ESI MS, that is, being supported by the isotope peak pattern authenticating the presence of Mg2+ in the complex. The L binds Mg2+ octahedrally using the tetradentate L2- and two additional acetic acid moieties by bringing conformational changes as studied on the basis of MM computations. The conformational changes that occur in the capped arms upon Mg2+ binding were supported experimentally by NOESY. AFM and SEM studies showed that spherical particles of L are modified into flower and chain type aggregates upon complexation with Mg2+, confirming the supramolecular behavior of the species formed.
- Nehra, Anita,Hinge, Vijaya Kumar,Rao, Chebrolu Pulla
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p. 5763 - 5770
(2014/07/08)
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- METHOD OF PREPARING POLY(ALKYLENE CARBONATE) VIA COPOLYMERIZATION OF CARBON DIOXIDE/EPOXIDE IN THE PRESENCE OF NOVEL COMPLEX
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Provided is a method of preparing poly(alkylene carbonate) using a molecular weight regulator in a process of preparing a copolymer of carbon dioxide/epoxide using a novel complex synthesized from salen-type ligand including a quaternary ammonium salt as a catalyst. According to the present invention, even though the molecular weight regulator is used, an activity of the catalyst may be stably maintained, whereby the low molecular weight of poly(alkylene carbonate) having a desirable level may be effectively provided. In addition, it is expected that since the novel complex as the catalyst of the present invention has a simple structure as compared to the existing copolymerization catalyst, due to the economical preparation cost thereof, the novel complex may be effectively applied to a large-scale commercial process.
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Paragraph 258; 259; 260; 261
(2014/10/04)
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- Facile one-pot transformation of phenols into o-cyanophenols
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The treatment of phenols with paraformaldehyde in the presence of MgCl2 and Et3N in THF at 80 C, followed by reaction with molecular iodine and aq. ammonia at room temperature provided the corresponding o-cyanophenols in moderate to good yields. The present reaction is a one-pot transformation of phenols into o-cyanophenols using much less expensive reagents than are typically used; the reaction is free of both transition-metals and cyanide. The utility of this reaction was highlighted during our preparation of Febuxostat from p-bromophenol.
- Nakai, Yuhta,Moriyama, Katsuhiko,Togo, Hideo
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p. 6077 - 6083
(2015/03/30)
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- Efficient cobalt-catalyzed oxidative conversion of lignin models to benzoquinones
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Phenolic lignin model monomers and dimers representing the primary substructural units of lignin were successfully oxidized to benzoquinones in high yield with molecular oxygen using new Co-Schiff base catalysts bearing a bulky heterocyclic nitrogen base as a substituent. This is the first example of a catalytic system able to convert both S and G lignin model phenols in high yield, a process necessary for effective use of lignin as a chemical feedstock.
- Biannic, Berenger,Bozell, Joseph J.
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supporting information
p. 2730 - 2733
(2013/07/26)
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- Synthesis of chromones through LiOtBu/air-mediated oxidation and regioselective cyclization of o-hydroxyphenyl propargyl carbinols
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A cascade oxidative cyclization reaction for the synthesis of chromone derivatives was developed by using LiOtBu as a mediator and air as an oxidant. The reaction was carried out without the assistance of a transition metal under mild conditions to afford the chromones in good yields with high regioselectivities. A tandem reaction for the synthesis of various chromones was developed. LiOtBu was used as a mediator and air was used as a clean oxidant. The reaction generally showed high regioselectivity under mild conditions. Extensive research showed that dehydrogenative oxidation of the alcohols under strongly basic conditions was the crucial step, and Li+ was also found to play an important role in this process. Copyright
- Zhang, Shuai,Wan, Changfeng,Wang, Qiang,Zhang, Baiqun,Gao, Lingfeng,Zha, Zhenggen,Wang, Zhiyong
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supporting information
p. 2080 - 2083
(2013/05/09)
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- Synthesis and characterization of new extractants for Cu(II)
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New extractants for Cu2+ ions in raw ore powders or waste water (fluid) were successfully synthesized recently in good yields. Their structures and purity were confirmed by 1H NMR and IR.
- Zhang, Xing,Hui, Jianbin
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p. 4229 - 4231
(2013/07/25)
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- Cooperative Al(salen)-pyridinium catalysts for the asymmetric synthesis of trans-configured β-lactones by [2+2]-cyclocondensation of acylbromides and aldehydes: Investigation of pyridinium substituent effects
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The trans-selective catalytic asymmetric formation of β-lactones constitutes an attractive surrogate for anti-aldol additions. Recently, we have reported the first catalyst which is capable of forming trans-β-lactones with high enantioselectivity from aliphatic (and aromatic) aldehyde substrates by cyclocondensation with acyl bromides. In that previous study the concepts of Lewis acid and organic aprotic ion pair catalysis were combined in a salen-type catalyst molecule. Since a pyridinium residue on the salen periphery is essential for high trans- and enantioselectivity, we were interested in the question of whether substituents on the pyridinium rings could be used to further improve the catalyst efficiency, as they might have a significant impact on the effective charges within the heterocycles. In the present study we have thus compared a small library of aluminum salen/bispyridinium catalysts mainly differing in the substituents on the pyridinium residues. As one result of these studies a new catalyst was identified which offers slightly superior stereoselectivity as compared to the previously reported best catalyst. NBO calculations have revealed that the higher stereoselectivity can arguably not be explained by the variation of the effective charge.
- Meier, Patrick,Broghammer, Florian,Latendorf, Katja,Rauhut, Guntram,Peters, Rene
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experimental part
p. 7121 - 7150
(2012/09/07)
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- Imino-phenolic-pyridyl conjugates of calix[4]arene (L1 and L2) as primary fluorescence switch-on sensors for Zn2+ in solution and in HeLa cells and the recognition of pyrophosphate and ATP by [ZnL2]
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Pyridyl-based triazole-linked calix[4]arene conjugates, viz. L1 and L2, were synthesized and characterized. These two conjugates were shown to be selective and sensitive for Zn2+ among the 12 metal ions studied in HEPES buffer medium by fluorescence, absorption, and visual color change with the detection limit of ～31 and ～112 ppb, respectively, by L1 and L2. Moreover, the utility of the conjugates L 1 and L2 in showing the zinc recognition in live cells has also been demonstrated using HeLa cells as monitored by fluorescence imaging. The zinc complexes of L1 and L2 were isolated, and the structure of [ZnL1] has been established by single-crystal XRD and that of [ZnL2] by DFT calculations. TDDFT calculations were performed in order to demonstrate the electronic properties of receptors and their zinc complexes. The isolated zinc complexes, viz. [ZnL1] and [ZnL 2], have been used as molecular tools for the recognition of anions on the basis of their binding affinities toward Zn2+. [ZnL 2] was found to be sensitive and selective toward phosphate-bearing ions and molecules and in particular to pyrophosphate (PPi) and ATP among the other 18 anions studied; however, [ZnL1] was not sensitive toward any of the anions studied. The selectivity has been shown on the basis of the changes observed in the emission and absorption spectral studies through the removal of Zn2+ from [ZnL2] by PPi. Thus, [ZnL 2] has been shown to detect PPi up to 278 ± 10 ppb at pH 7.4 in aqueous methanolic (1/2 v/v) HEPES buffer.
- Kumar Pathak, Rakesh,Kumar Hinge, Vijaya,Rai, Ankit,Panda, Dulal,Pulla Rao, Chebrolu
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scheme or table
p. 4994 - 5005
(2012/06/15)
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- Enantioselective intramolecular formal [2 + 4] annulation of acrylates and α,β-unsaturated imines catalyzed by amino acid derived phosphines
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The first chiral phosphine-catalyzed activation of acrylates for intramolecular formal [2 + 4] reactions with unsaturated imines is described. The catalytic reactions afford N-heterocycles with exceptionally high diastereo- and enantioselectivities. The [2 + 4] products are amenable for further transformations to useful molecules such as chiral piperidines and multicyclic structures.
- Jin, Zhichao,Yang, Ruojie,Du, Yu,Tiwari, Bhoopendra,Ganguly, Rakesh,Chi, Yonggui Robin
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supporting information; experimental part
p. 3226 - 3229
(2012/08/08)
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- Triazole linked picolylimine conjugate of calix[6]arene as a sequential sensor for La3+ followed by F-
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A new 1,3,5-tris-triazole linked picolylimine conjugate of calix[6]arene (L) has been shown to be selective toward La3+ by turn on fluorescence with ～70-fold enhancement and emits blue, with a minimal detection limit of 65 ± 5 ppb (490 nM). The species of recognition has been modeled computationally to have a monocapped twisted square antiprism with a N6O3 binding core about La3+. The in situ complex of L with La3+ recognizes F- via fluorescence quenching. The reversible response of sensing La3+ and F- sequentially by L has been demonstrated.
- Mummidivarapu, V. V. Sreenivasu,Nehra, Anita,Hinge, Vijaya Kumar,Rao, Chebrolu P.
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scheme or table
p. 2968 - 2971
(2012/09/22)
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- Triazole-linked-thiophene conjugate of calix[4]arene: Its selective recognition of Zn2+ and as biomimetic model in supporting the events of the metal detoxification and oxidative stress involving metallothionein
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Supramolecular calix[4]arene conjugate (L) has been developed as a sensitive and selective sensor for Zn2+ in HEPES buffer among the 12 metal ion by using fluorescence, absorption and ESI MS and also by visual fluorescent color. The structural, electronic, and emission properties of the calix[4]arene conjugates L and its zinc complex, [ZnL], have been demonstrated using ab initio density functional theory (DFT) combined with time-dependent density functional theory (TDDFT) calculations. The TDDFT calculations reveal the switch on fluorescence behavior of L is mainly due to the utilization of the lone pair of electrons on imine moiety by the Zn2+. The resultant fluorescent complex, [ZnL], has been used as a secondary sensing chemo-ensemble for the detection of -SH containing molecules by removing Zn2+ from [ZnL] and forming {Cys/DTT·Zn} adducts as equivalent to those present in metallothioneins. The displacement followed by the release of the coordinated zinc from its Cys/DTT complex by heavy metal ion (viz. Cd2+ and Hg2+), as in the metal detoxification process or by ROS (such as H2O2) as in the oxidative stress, has been well demonstrated using the conjugate L through the fluorescence intensity retrieval wherein the fluorescence intensity is the same as that observed with [ZnL], which in turn mimics the zinc sensing element (MTF) in biology (Figure presented).
- Pathak, Rakesh Kumar,Hinge, Vijaya Kumar,Mondal, Milon,Rao, Chebrolu Pulla
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experimental part
p. 10039 - 10049
(2012/02/06)
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- Calix[4]arene-based 1,3-diconjugate of salicylyl imine having dibenzyl amine moiety (L): Synthesis, characterization, receptor properties toward Fe2+, Cu2+, and Zn2+, crystal structures of its Zn2+ and Cu2+ complexes, and selective phosphate sensing by the [ZnL]
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A calix[4]arene conjugate bearing salicylyl imine having dibenzyl moiety (L) has been synthesized and characterized, and its ability to recognize three most important essential elements of human system, viz., iron, copper, and zinc, has been addressed by colorimetry and fluorescence techniques. L acts as a sensor for Cu2+ and Fe2+ by exhibiting visual color change and for Zn2+ based on fluorescence spectroscopy. L shows a minimum detection limit of 3.96 ± 0.42 and 4.51 ± 0.53 ppm and 45 ± 4 ppb, respectively, toward Fe2+, Cu2+, and Zn 2+. The in situ prepared [ZnL] exhibits phosphate sensing among 14 anions studied with a detection limit of 247 ± 25 ppb. The complexes of Zn2+, Cu2+, and Fe2+ of L have been synthesized and characterized by different techniques. The crystalline nature of the zinc and copper complexes and the noncrystalline nature of simple L and its iron complex have been demonstrated by powder XRD. The structures of Cu2+ and Zn2+ complexes have been established by single crystal XRD wherein these were found to be 1:1 monomeric and 2:2 dimeric, respectively, using N2O2 as binding core. The geometries exhibited by the Zn2+ and the Cu2+ complexes were found to be distorted tetrahedral and distorted square planar, respectively. The iron complex of L exists in 1:1 stoichiometry as evident from the mass spectrometry and elemental analysis.
- Joseph, Roymon,Chinta, Jugun Prakash,Rao, Chebrolu P.
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scheme or table
p. 7050 - 7058
(2011/09/20)
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- Selective recognition of cysteine in its free and protein-bound states by the Zn2+ complex of a triazole-based calix[4]arene conjugate
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Zinc-ed in: A highly fluorescent zinc complex of triazole-linked calix[4]arene (see scheme), [ZnL], for the selective recognition of Cys and other protein-bound/free thiols in the blood-serum milieu by mimicking the Zn2+-induced redox switch has been developed. Copyright
- Kumar Pathak, Rakesh,Tabbasum, Khatija,Kumar Hinge, Vijaya,Pulla Rao, Chebrolu
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supporting information; scheme or table
p. 13999 - 14003
(2012/01/06)
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- Mononuclear iron(III) complexes supported by tripodal N3O ligands: Synthesis, structure and reactivity towards DNA cleavage
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A new synthetic route to the known tripodal tetradentate N3O ligand L1 (HL1 = [N-(3,5-di-tert-butyl-2-hydroxybenzyl)-N,N-di-(2-pyridylmethyl)]amine) is reported. The related compounds HLn (n = 2, 3) were prepared by a similar procedure. Treatment of HLn (n = 1-3) with FeCl3·6H2O in hot methanol led to the mononuclear iron(III) complexes [Fe(Ln)Cl2] (1: n = 1, 2: n = 2, 3: n = 3). The solid-state structures of complexes 1 and 2 were determined by X-ray crystallography. [Fe(L1)Cl2] (1) showed effective nuclease activity in the presence of hydrogen peroxide, converting supercoiled plasmid DNA to its linear form.
- Wong, Yee-Lok,Mak, Chun-Yin,Kwan, Hoi Shan,Lee, Hung Kay
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experimental part
p. 1246 - 1253
(2010/07/05)
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- New dioxo-molybdenum(vi) and -tungsten(vi) complexes with N-capped tripodal N2O2 tetradentate ligands: Synthesis, structures and catalytic activities towards olefin epoxidation
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A series of N2O2 tripodal tetradentate ligands derived from di-/tetra-tert-butyl substituted 2-[bis(2-hydroxybenzyl) aminomethyl]X (X = pyridine and benzimidazole) (H2Ln (n = 1-4)) and 8-[bis(3,5-di-tert-butyl-2-hydroxybenzyl)]aminoquinoline (H 2L5) were synthesised through a 4-step reaction scheme involving sequential formylation, reduction, bromination and alkylation. Treatment of H2Ln (n = 1-5) with [WO2Cl 2(dme)] (dme = 1,2-dimethoxyethane) in the presence of triethylamine gave the corresponding cis-dioxotungsten(vi) complexes [WO2(L n)] (n = 1-5). The corresponding molybdenum analogues [MoO 2(Ln)] (n = 1-5) were also prepared from the reaction of [MoO2(acac)2] (acac = acetylacetonate) with H 2Ln (n = 1-3) or [MoO2Cl2(dme)] (dme = 1,2-dimethoxyethane) with H2Ln (n = 4 and 5). All these compounds were fully characterised by a wide range of spectroscopic methods. The molecular structures of [MoO2(Ln)] (n = 2, 4) and [WO2(L2)] were also confirmed by single-crystal X-ray diffraction analysis. The catalytic activities of [MO2(L n)] (M = Mo, W; n = 1-4) towards epoxidation of styrene were also examined.
- Wong, Yee-Lok,Tong, Lok H.,Dilworth, Jonathan R.,Ng, Dennis K. P.,Lee, Hung Kay
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supporting information; experimental part
p. 4602 - 4611
(2010/08/22)
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- A lower rim triazole linked calix[4]arene conjugate as a fluorescence switch on sensor for Zn2+ in blood serum milieu
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A fluorescence turn-on receptor based on triazole linked calix[4]arene (L) for selective recognition of Zn2+ in aqueous-methanolic HEPES buffer has been developed and showed its utility for sensing Zn2+ in blood serum milieu.
- Pathak, Rakesh Kumar,Dikundwar, Amol G.,Row, Tayur N. Guru,Rao, Chebrolu Pulla
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supporting information; scheme or table
p. 4345 - 4347
(2010/08/04)
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- MODULATORS OF CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR
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This invention relates to a compound of Formula I or a pharmaceutically acceptable salt thereof, wherein R is COOH or CH2OH.
- -
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Page/Page column 14-15; 34-36; 45
(2010/10/03)
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- PROCESS FOR MAKING MODULATORS OF CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR
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The invention provides a process for the preparation of a compound of Formula 1; comprising coupling a carboxylic acid of Formula 2; with an aniline of Formula 3; in the presence of a coupling agent.
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Page/Page column 64-66; 75
(2010/10/03)
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- Palladium(0)-catalyzed intramolecular heck reaction: A resourceful route for the synthesis of naphthoxepine naphthoxocine derivatives
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The synthesis of oxocines and oxepines is difficult. Two efficient protocols have been developed for the construction of naphthoxepine and naphthoxocine derivatives by sequential Wittig olefination and intramolecular Heck reaction. Georg Thieme Verlag Stuttgart.
- Majumdar,Ansary, Inul,Sinha, Biswajit,Chattopadhyay, Buddhadeb
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experimental part
p. 3593 - 3602
(2010/03/03)
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- Reductive deoxygenation of ortho-hydroxyaromatic aldehydes to 1,2-bis(hydroxyaryl)ethanes: application to the synthesis of ethylene bridged calixarene-analogous metacyclophanes
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A novel and convenient protocol for the synthesis of hexahydroxy[2.1.2.1.2.1]- and octahydroxy[2.1.2.1.2.1.2.1]metacyclophanes from 4-substituted phenol in four steps has been developed. The synthetic route involved the preparation of the key intermediate 1,2-bis(5-substituted-2-hydroxyphenyl)ethanes in good yields via (i) formylation of 4-substituted phenol, (ii) reductive deoxygenation of 5-substituted 2-hydroxy aromatic aldehydes with low-valent titanium reagent and (iii) catalytic hydrogenation. The metacyclophanes were prepared by base-catalyzed macrocyclization of the above intermediates with formaldehyde in refluxing xylene in high yields.
- Bhatt, Suchitra,Nayak, Sandip K.
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experimental part
p. 5823 - 5826
(2010/01/11)
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- Phthalides by rhodium-catalyzed ketone hydroacylation
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(Chemical Equation Presented) Phthalides are biologically relevant five-membered lactones found in herbs, fruits, and vegetables. Herein we communicate the first atom-economical approach to phthalides by using enantioselective ketone hydroacylation. In the presence of Rh[(Duanphos)]X (X = NO3, OTf, OMs), various 2-ketobenzaldehydes undergo intramolecular hydroacylation to produce phthalide products in good yields and 92-98% ee's. Our study highlights the key role counterions play in controlling both reactivity and enantioselectivity. A concise asymmetric total synthesis of the celery extract (S)-(-)-3-n-butylphthalide is also presented.
- Phan, Diem H. T.,Kim, Byoungmoo,Dong, Vy M.
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supporting information; experimental part
p. 15608 - 15609
(2010/01/30)
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- Asymmetric Henry reaction catalyzed by a copper tridentate chiral schiff-base complex
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A series of copper-tridentate chiral Schiff-base complexes were prepared and employed in an asymmetric Henry reaction, affording the corresponding adducts in good yields and with high enantioselectivities (up to 96% ee).
- Lai, Guoyin,Wang, Sujing,Wang, Zhiyong
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p. 1813 - 1819
(2008/12/22)
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- Polyacidic multiloading metal extractants
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Novel polynucleating, di- and tri-acidic ligands have been designed to increase the molar and mass transport efficiencies for the recovery of base metals by solvent extraction. The Royal Society of Chemistry.
- Gordon, Ross J.,Campbell, John,Henderson, David K.,Henry, Dorothy C. R.,Swart, Ronald M.,Tasker, Peter A.,White, Fraser J.,Wood, Jenny L.,Yellowlees, Lesley J.
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supporting information; experimental part
p. 4801 - 4803
(2009/03/12)
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- Synthesis of chromanones: A novel palladium-catalyzed Wacker-type oxidative cyclization involving 1,5-hydride alkyl to palladium migration
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A series of 2-methylchromanone derivatives have been prepared by using a novel palladium-catalyzed Wacker-type oxidative cyclization, in which a 1,5-hydride alkyl to palladium migration and a direct chirality transfer were involved. The Royal Society of Chemistry.
- Zhang, Zuhui,Pan, Chongfeng,Wang, Zhiyong
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p. 4686 - 4688
(2008/10/09)
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- Microwave assisted synthesis of 4-alkyl-2-([5-substituted-2-hydroxyphenyl]- iminomethyl)benzenols and their NMR characterization
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Imines, 4-alkyl-2-([5-substituted-2-hydroxyphenyl]iminomethyl)-benzenols 1, have been obtained successfully in excellent yield from the corresponding aldehydes and amines by microwave irradiation. The resultant Schiff bases have been fully characterized by spectral data.
- Sridharan,Muthusubramanian,Sivasubramanian
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p. 416 - 419
(2007/10/03)
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- Copper(II) complexes of thioether-substituted salcyen and salcyan derivatives and their silver(I) adducts
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New syntheses are reported of 5-tert-butyl-2-hydroxy-3- methylsulfanylbenzaldehyde, 5-tert-butyl-2-hydroxy-3-phenylsulfanyl- benzaldehyde, and salcyen (H2L1-H2L 3) and salcyan (H2L4-H2L 6)-type ligands derived from these aldehydes and from 5-tert-butyl-2-hydroxybenzaldehyde. The complexes [CuL] (L2- = [L1]2--[L6]2-) bearing sulfanyl substituents each show two distinct voltammetric ligand-based oxidations under the same conditions, the first of which is chemically reversible. The first oxidation product is much longer lived by coulometry for the salcyen than for the salcyan ligand complexes, despite the latter having a substantially lower oxidation potential. The lifetimes of all the ligand oxidation products in this system are substantially smaller than for similar compounds derived from 3,5-di(tert-butyl)-2-hydroxybenzaldehyde (Dalton Trans., 2004, 2662). Attempted chemical oxidation of the Schiff base compounds using AgBF4 yielded instead stable silver(I) adducts. A crystal structure of one such compound showed that the Ag atom was coordinated in a slightly bent geometry by the two ligand sulfanyl groups, with two additional long-range Ag ... O interactions to the phenoxide donors. EPR spectra showed that some of these silver adducts dimerise in CH2Cl2, probably through basal, apical intermolecular Cu-O ... Cu bridging. In contrast the parent copper(II) complexes are all monomeric in this solvent by EPR. The Royal Society of Chemistry 2005.
- Sylvestre, Isabelle,Wolowska, Joanna,Kilner, Colin A.,McInnes, Eric J. L.,Halcrow, Malcolm A.
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p. 3241 - 3249
(2007/10/03)
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- Synthesis and characterisation of a high valent dinuclear Mn(III,III) complex of a triphenolate ligand [N4O3]3- with two extra functional groups
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A new high valent complex [Mn2(III,III)L(μ-OAc) 2]·PF6 7 was prepared, where L was the tri-anion of 2,6-Bis {[(2-hydroxy-5-tert-butylbenzyl)(pyridyl-2-methyl)amino]methyl}-4-methylphenol which contained two additional phenolate groups and two tert-butyl groups compared to its parent [Mn2(II,II)(bpmp)(μ-OAc) 2]·PF6. These improvements narrowed the disparity between the new model and (Mn)4 cluster (OEC in nature).
- Li, Hongyang,Shi, Feng,Gao, Yan,Zhang, Rong,Peng, Xiaojun,Sun, Licheng
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- Ligand tuning in the chromium-salen-mediated asymmetric epoxidation of alkenes
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A series of Cr(salen) complexes have been synthesised from 5-substituted-3-bromosalicylaldehydes and trans-1,2-cyclohexanediamine. These have been used to probe the Cr(salen)-mediated asymmetric epoxidation of alkenes. No simple correlation was found between the electronic character of the salen-substituents and the enantioselectivity - multiple oxidation pathways are proposed as a possible explanation. Enantioselectivities of up to 90% have been achieved using a novel, synthetically accessible Cr(salen) complex.
- McGarrigle,Murphy,Gilheany
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p. 1343 - 1354
(2007/10/03)
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- Selectivity in the photodimerization of 6-alkylcoumarins
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Coumarin and 6-alkylcoumarins (alkyl = C1 to C16) were photodimerized in homogeneous solvents differing in polarity and in aqueous micellar solutions. The four possible photodimers, syn head-to-head (hh), anti head-to-head, syn head-to-tail (ht), and anti head-to-tail, were identified through a combination of X-ray analysis and NMR spectroscopy. In 6-methylcoumarin the concentration-corrected dimerization (quantum) yield increases with decreasing concentration of the educt; anti- hh was formed exclusively in nonpolar solvents and upon triplet sensitization and was the main product under all conditions except for ionic micellar systems, which direct to preferred syn-hh dimerization. Long alkyl substituents, however, lead to anti-hh in polar solvents and in micelles, too. Predominating ht dimer formation was observed for nonsubstituted coumarin in polar solvents only. Thus, syn/anti and hh/ht selectivity can be steered by varying the 6-alkyl substituent. Syn- hh photodimers of 6-methylcoumarin can be photochemically split into the monomers; they partly proved thermally unstable against acids, bases, methanol, and on SiO2 surfaces.
- Yu, Xiuling,Scheller, Dieter,Rademacher, Otto,Wolff, Thomas
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p. 7386 - 7399
(2007/10/03)
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- Synthesis of a tridentate ligand for use in TiIV-catalyzed acetate aldol addition reactions
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A facile, practical synthesis and resolution of (±) -2′-amino-[1,1′-binaphthalen]-2-ol (1) is described, as well as the preparation of the tridentate Schiff base ligand 2 derived from condensation of 1 with 3-bromo-5-(tert-butyl)salicylaldehyde, which has been used in catalytic enantioselective acetate aldol addition reactions.
- Singer, Robert A.,Brock, Jane R.,Carreira, Erick M.
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p. 1040 - 1044
(2007/10/03)
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- Biaryl-bridged Schiff base complexes of zirconium alkyls: Synthesis structure and stability
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Three substituted salicylaldimine derivatives H2 L1-3 of 2,2′-diamino-6,6′-dimethylbiphenyl give, under appropriate conditions, isolable alkyls of zirconium [ZrL1-3R2] (R=CH2Ph, CH2 But). Two molecular structures confirm their cis-α geometry (C2-symmetric with cis alkyl ligands). They decompose via 1,2-migratory insertion of an alkyl group to imine, followed in some instances by a second similar reaction. The dimeric molecular structure of one such doubly-inserted product is presented. The kinetics of decomposition by this process are studied briefly, and it is noted that the rate increases with increased steric demand of the salicylaldimine unit.
- Knight, Paul D.,O'Shaughnessy, Paul N.,Munslow, Ian J.,Kimberley, Brian S.,Scott, Peter
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p. 103 - 113
(2007/10/03)
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- The separation and synthesis of lipidic 1,2- and 1,3-diols from natural phenolic lipids for the complexation and recovery of boron
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A study has been made of the semi-synthesis of 1,3-diols (anacardic alcohols) from natural phenolic lipid resources from Anacardium occidentale and Anacardium giganteum which have given C15 and C11 derivatives, respectively. An isomeric 1,3-diol (isoanacardic alcohol) has been obtained from cardanol separated from technical cashew nut-shell liquid. Homologous1,3-diols have been synthesised from a range of synthetic 2-alkyl-, 3-alkyl- and 4-alkylphenols and from 6-alkylsalicylic acids. The natural 1,2-diol, urushiol, from Rhus vernicifera has been purified. All these lipidic compounds have been studied for their complexation and the potential recovery of boron as boric acid.
- Tyman, John H.P.,Mehet, Satinderjit K.
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p. 177 - 199
(2007/10/03)
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