Chemistry—A European Journal is a truly international journal with top quality contributions (2018 ISI Impact Factor: 5.16). It publishes a wide range of outstanding Reviews, Minireviews, Concepts, Full Papers, and Communications from all areas of chemistry and related fields. Based in Europe Chemistry—A European Journal provides an excellent platform for increasing the visibility of European chemistry as well as for featuring the best research from authors from around the world. All manuscripts are peer-reviewed, and electronic processing ensures accurate reproduction of text and data, plus short publication times. The Concepts section provides nonspecialist readers with a useful conceptual guide to unfamiliar areas and experts with new angles on familiar problems. Chemistry—A European Journal is published on behalf of ChemPubSoc Europe, a group of 16 national chemical societies from within Europe, and supported by the Asian Chemical Editorial Societies. The ChemPubSoc Europe family comprises: Angewandte Chemie, Chemistry—A European Journal, European Journal of Organic Chemistry, European Journal of Inorganic Chemistry, ChemPhysChem, ChemBioChem, ChemMedChem, ChemCatChem, ChemSusChem, ChemPlusChem, ChemElectroChem, and ChemistryOpen.
AbstractThe NMR parameters (1H and 13C chemical shifts and coupling constants) for a series of naturally occurring molecules have been calculated mostly with DFT methods, and their spectra compared with available experimental ones. The comparison includes strychnine as a test case, as well as some examples of recently isolated natural products (corianlactone, daphnipaxinin, boletunone B) featuring unusual and/or crowded structures and, in the case of boletunone B, being the subject of a recent revision. Whenever experimental spectra were obtained in polar solvents, the calculation of NMR parameters was also carried out with the Integral Equation‐Formalism Polarizable Continuum Model (IEF‐PCM) continuum method. The computed results generally show a good agreement with experiment, as judged not only by statistical parameters but also by visual comparison of line spectra. The origin of the remaining discrepancies is attributed to the incomplete modeling of conformational and specific solvent effects.
Atanu Jana, Luke K. McKenzie, Ashley B. Wragg, Masatoshi Ishida, Jonathan P. Hill, Julia A. Weinstein, Elizabeth Baggaley, Michael D. Ward
AbstractA new class of substituted porphyrins has been developed in which a different number of cyclometalated PtII C^N^N acetylides and polyethylene glycol (PEG) chains are attached to the meso positions of the porphyrin core, which are meant for photophysical, electrochemical, and in vitro light‐induced singlet oxygen (1O2) generation studies. All of these ZnII porphyrin–PtII C^N^N acetylide conjugates show moderate to high (ΦΔ=0.55 to 0.63) singlet oxygen generation efficiency. The complexes are soluble in organic solvents but, despite the PEG substituents, slowly aggregate in aqueous solvent systems. These conjugates also exhibit interesting photophysical properties, including near‐complete photoinduced energy transfer (PEnT) through the rigid acetylenic bond(s) from the PtII C^N^N antenna units to the ZnII porphyrin core, which shows sensitized luminescence, as shown by quenching of PtII C^N^N‐based luminescence. Electrochemical measurements show a set of redox processes that are approximately the sum of what is observed for the PtII C^N^N acetylide and ZnII porphyrin units. UV/Vis spectroscopic properties are supported by DFT calculations.
Ping Wang, Chung‐Hang Leung, Dik‐Lung Ma, Siu‐Cheong Yan, Chi‐Ming Che
AbstractA series of platinum(II) complexes with tridentate ligands was synthesized and their interactions with G‐quadruplex DNA within the c‐myc gene promoter were evaluated. Complex 1, which has a flat planar 2,6‐bis(benzimidazol‐2‐yl)pyridine (bzimpy) scaffold, was found to stabilize the c‐myc G‐quadruplex structure in a cell‐free system. An in silico G‐quadruplex DNA model has been constructed for structure‐based virtual screening to develop new PtII‐based complexes with superior inhibitory activities. By using complex 1 as the initial structure for hit‐to‐lead optimization, bzimpy and related 2,6‐bis(pyrazol‐3‐yl)pyridine (dPzPy) scaffolds containing amine side‐chains emerge as the top candidates. Six of the top‐scoring complexes were synthesized and their interactions with c‐myc G‐quadruplex DNA have been investigated. The results revealed that all of the complexes have the ability to stabilize the c‐myc G‐quadruplex. Complex 3 a ([PtIIL2R]+; L2=2,6‐bis[1‐(3‐piperidinepropyl)‐1H‐enzo[d]imidazol‐2‐yl]pyridine, R=Cl) displayed the strongest inhibition in a cell‐free system (IC50=2.2 μM) and was 3.3‐fold more potent than that of 1. Complexes 3 a and 4 a ([PtIIL3R]+; L3=2,6‐bis[1‐(3‐morpholinopropyl)‐1H‐pyrazol‐3‐yl]pyridine, R=Cl) were found to effectively inhibit c‐myc gene expression in human hepatocarcinoma cells with IC50 values of ≈17 μM, whereas initial hit 1 displayed no significant effect on gene expression at concentrations up to 50 μM. Complexes 3 a and 4 a have a strong preference for G‐quadruplex DNA over duplex DNA, as revealed by competition dialysis experiments and absorption titration; 3 a and 4 a bind G‐quadruplex DNA with binding constants (K) of approximately 106–107 dm3 mol−1, which are at least an order of magnitude higher than the K values for duplex DNA. NMR spectroscopic titration experiments and molecular modeling showed that 4 a binds c‐myc G‐quadruplex DNA through an external end‐stacking mode at the 3′‐terminal face of the G‐quadruplex. Intriguingly, binding of c‐myc G‐quadruplex DNA by 3 b is accompanied by an increase of up to 38‐fold in photoluminescence intensity at λmax=622 nm.
Noora Svahn, Artur J. Moro, Catarina Roma‐Rodrigues, Rakesh Puttreddy, Kari Rissanen, Pedro V. Baptista, Alexandra R. Fernandes, João Carlos Lima, Laura Rodrı́guez
AbstractA series of 4‐ethynylaniline gold(I) complexes containing monophosphane (1,3,5‐triaza‐7‐phosphaadamantane (pta; 2), 3,7‐diacetyl‐1,3,7‐triaza‐5‐phosphabicyclo[3.3.1]nonane (3), and PR3, with R=naphthyl (4), phenyl (5), and ethyl (6)) and diphosphane (bis(diphenylphosphino)acetylene (dppa; 7), trans‐1,2‐bis(diphenylphosphino)ethene (dppet; 8), 1,2‐bis(diphenylphosphino)ethane (dppe; 9), and 1,3‐bis(diphenylphosphino)propane (dppp; 10)) ligands have been synthesized and their efficiency against tumor cells evaluated. The cytotoxicity of complexes 2–10 was evaluated in human colorectal (HCT116) and ovarian (A2780) carcinoma as well as in normal human fibroblasts. All the complexes showed a higher antiproliferative effect in A2780 cells, with the cytotoxicity decreasing in the following order 5>6=9=10>8>2>4>7>3. Complex 4 stands out for its very high selectivity towards ovarian carcinoma cells (IC50=2.3 μm) compared with colorectal carcinoma and normal human fibroblasts (IC50>100 μm), which makes this complex very attractive for ovarian cancer therapy. Its cytotoxicity in these cells correlates with the induction of the apoptotic process and an increase of intracellular reactive oxygen species (ROS). The effects of the nuclearity, rigidity, and solubility of these complexes on their biological activity were also analyzed. X‐ray crystal structure determination allowed the identification of short N−H⋅⋅⋅π contacts as the main driving forces for the three‐dimensional packing in these molecules.
Cong Yu, Kenneth Chan, Keith Man‐Chung Wong, Vivian Wing‐Wah Yam
AbstractPolyelectrolytes carrying multiple negative charges were found to induce the aggregation and self‐assembly of the positively charged platinum(II)–terpyridyl complexes in aqueous media. The aggregation and self‐assembly of the complexes were driven by electrostatic interactions between the polymer and the complex, and by terpyridine ligand π–π stacking and platinum–platinum (metal–metal) interactions. As a result, remarkable UV/Vis and emission spectral changes were observed. The spectroscopic property changes were related to the structural properties of the metal complexes as well as the polyelectrolytes. The induced self‐assembly of the platinum complexes was also strongly affected by the solution properties of the aqueous media, for example, the solution pH, ionic strength, and the percentage of organic solvent added.
Kun Huang, Yuanjian Zhang, Yun‐Ze Long, Junhua Yuan, Dongxue Han, Zhijuan Wang, Li Niu, Zhaojia Chen
AbstractOne‐dimensional gold/polyaniline (Au/PANI‐CSA) coaxial nanocables with an average diameter of 50–60 nm and lengths of more than 1 μm were successfully synthesized by reacting aniline monomer with chlorauric acid (HAuCl4) through a self‐assembly process in the presence of D‐camphor‐10‐sulfonic acid (CSA), which acts as both a dopant and surfactant. It was found that the formation probability and the size of the Au/PANI‐CSA nanocables depends on the molar ratio of aniline to HAuCl4 and the concentration of CSA, respectively. A synergistic growth mechanism was proposed to interpret the formation of the Au/PANI‐CSA nanocables. The directly measured conductivity of a single gold/polyaniline nanocable was found to be high (≈77.2 S cm−1). Hollow PANI‐CSA nanotubes, with an average diameter of 50–60 nm, were also obtained successfully by dissolving the Au nanowire core of the Au/PANI‐CSA nanocables.
AbstractThe biheteroaryl structural motif is prevalent in polymers, advanced materials, liquid crystals, ligands, molecules of medicinal interest, and natural products. Many types of synthetic transformations have been known for the construction of heteroaryl–heteroaryl linkages. Coupling reactions provide one of the most efficient ways to achieve these biheterocyclic structures. In this review, four types of coupling reactions are discussed: 1) transition‐metal‐catalyzed coupling reactions of heteroaryl halides or surrogates with heteroarylmetals; 2) direct inter‐ and intramolecular heteroarylations of CH bonds of heteroarenes with heteroaryl halides or pseudohalides; 3) oxidative CH/CH homo‐ and cross‐couplings of two unpreactivated heteroarenes; and 4) transition‐metal‐catalyzed decarboxylative cross‐coupling reactions between haloheteroarenes or heteroarenes and heteroarenecarboxylic acids. The general purpose of this review is to give an exhaustive and clear picture in heteroaryl–heteroaryl bond formation as well as its application in the synthesis of natural products, pharmaceuticals, catalyst ligands, and materials.
Yajun Li, Jiangtao Zhu, Lisi Zhang, Yongming Wu, Yuefa Gong
AbstractA highly efficient method for the synthesis of fluorine‐containing multisubstituted phenanthridines through Rh‐catalyzed alkyne [2+2+2] cycloaddition reactions has been developed. This method exhibits excellent functional‐group compatibility. When a bromodifluoromethyl group, rather than a trifluoromethyl group, was employed in the cycloaddition reaction, more‐complicated polycyclic compounds were obtained through tandem Rh‐catalyzed cycloaddition/CH difluoromethylenation. This route provides convenient access to fluorine‐containing polycyclic compounds.
Chỉ số ảnh hưởng
Total publication
124
Total citation
15,159
Avg. Citation
122.25
Impact Factor
0
H-index
59
H-index (5 years)
59
i10
121
i10-index (5 years)
9
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