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Articles from Wiley

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The latest chemistry from ChemPubSoc Europe and Wiley-VCH
Aggiornato: 7 settimane 5 giorni fa

Corrigendum: Phosphatase-Stable Phosphoamino Acid Mimetics That Enhance Binding Affinities with the Polo-Box Domain of Polo-like Kinase 1

23 gennaio, 2017 - 00:00

[Corrigendum]
David Hymel, Terrence R. Burke
ChemMedChem, January 23, 2017, DOI: 10.1002/cmdc.201700019. Read article

Cover Picture: Structural Simplification of Bedaquiline: the Discovery of 3-(4-(<i>N</i>,<i>N</i>-Dimethylaminomethyl)phenyl)quinoline-Derived Antitubercular Lead Compounds (ChemMedChem 2/2017)

23 gennaio, 2017 - 00:00

 the Discovery of 3‐(4‐(N,N‐Dimethylaminomethyl)phenyl)quinoline‐Derived Antitubercular Lead Compounds (ChemMedChem 2/2017)

The front cover picture shows a molecular model of a bacterial rotary ATP synthase, which is targeted and inhibited by the novel antituberculosis (TB) drug Bedaquiline (Sirturo®), the first anti-TB antibiotic compound in 40 years. Bedaquiline synthesis is expensive, mainly due to two chiral centers within the molecule. Using a fragment based synthesis approach He, Preiss et al. present an economical way of producing Bedaquiline derivatives with no chiral centers that still maintain antitubercular activity against Mycobacterium tuberculosis. More information can be found in the Full Paper by Huaqing Cui, Thomas Meier, Dali Yin et al. on page 106 in Issue 2, 2017 (DOI: 10.1002/cmdc.201600441). (The picture was drawn by Dr. Laura Preiss.)

[Cover Picture]
Chunxian He, Laura Preiss, Bin Wang, Lei Fu, Hui Wen, Xiang Zhang, Huaqing Cui, Thomas Meier, Dali Yin
ChemMedChem, January 23, 2017, DOI: 10.1002/cmdc.201600625. Read article

Synthesis and Biological Evaluation of Amidinourea and Triazine Congeners as Inhibitors of MDA-MB-231 Human Breast Cancer Cell Proliferation

23 gennaio, 2017 - 00:00

Synthesis and Biological Evaluation of Amidinourea and Triazine Congeners as Inhibitors of MDA‐MB‐231 Human Breast Cancer Cell Proliferation

New class in the fight: Breast cancer is currently the second most lethal cancer among women, preceded only by lung cancer. Novel amidinourea derivatives were synthesized and evaluated as inhibitors of MDA-MB-231 breast cancer cell proliferation. Amidinourea 3 d was found to be active against MDA-MB-231 breast cancer cells with an IC50 value of 0.76 &#x3BC;m, close to the activity of tamoxifen.

[Communication]
Rosemary Bass, Sarah Jenkinson, Jennifer Wright, Tora Smulders-Srinivasan, Jamie C. Marshall, Daniele Castagnolo
ChemMedChem, January 23, 2017, DOI: 10.1002/cmdc.201600580. Read article

Metal NHC Complexes with Naphthalimide Ligands as DNA-Interacting Antiproliferative Agents

23 gennaio, 2017 - 00:00

Metal NHC Complexes with Naphthalimide Ligands as DNA‐Interacting Antiproliferative Agents

Naphthalimide-based N-heterocyclic carbene (NHC) complexes were synthesized and investigated as antiproliferative agents that target DNA. The cytotoxic effects were found to be largely driven by the naphthalimide structure, which is a DNA-intercalating moiety. One stable rhodium(I)–NHC complex shows especially potent cytotoxic effects, interacts strongly with DNA, and induces apoptosis via mitochondrial pathways.

[Full Paper]
Wojciech Streciwilk, Alessio Terenzi, Rainer Misgeld, Corazon Frias, Peter G. Jones, Aram Prokop, Bernhard K. Keppler, Ingo Ott
ChemMedChem, January 23, 2017, DOI: 10.1002/cmdc.201600557. Read article

Synthesis and Olfactory Properties of a 6′-Silasubstituted “Spiro[4.5]-δ-Damascone”

23 gennaio, 2017 - 00:00

Synthesis and Olfactory Properties of a 6′‐Silasubstituted “Spiro[4.5]‐&#x3B4;‐Damascone”

A difference of a small thorn on the rose olfactophore yet, with giant consequences for olfaction! The odor threshold of a thermally unstable 6’-silasubsituted target structure (silver) is 900 times weaker than the “spiro[4.5]-&#x3B4;-damascone” lead (gold). Its degradation product through an enol Brook rearrangement (black) is even 12 000 times weaker. The difference is only a slight extension of the upper hydrophobe (cyan), offering fine-tuned insights into the structural requirements of rose ketones. More information can be found in the Full Paper by P. Kraft, et al. (DOI: 10.1002/chem.201605378).

[Cover Picture]
Martin A. Lovchik, Philip Kraft
Chem. Eur. J., January 23, 2017, DOI: 10.1002/chem.201700122. Read article

A Very Short Be–Be Distance but No Bond: Synthesis and Bonding Analysis of Ng–Be<sub>2</sub>O<sub>2</sub>–Ng′ (Ng, Ng′=Ne, Ar, Kr, Xe)

23 gennaio, 2017 - 00:00

 Synthesis and Bonding Analysis of Ng–Be2O2–Ng′ (Ng, Ng′=Ne, Ar, Kr, Xe)

Faraway, so close! The homo- and heteroleptic noble gas complexes Ng−Be2O2−Ng′ (Ng, Ng′=Ne, Ar, Kr, Xe) that were prepared in low-temperature matrices possess a cyclic Be2O2 core with Be−Be distances that are shorter than a standard Be=Be double bond without a chemical bond.

[Communication]
Qingnan Zhang, Wan-Lu Li, Lili Zhao, Mohua Chen, Mingfei Zhou, Jun Li, Gernot Frenking
Chem. Eur. J., January 23, 2017, DOI: 10.1002/chem.201605994. Read article

Exploring the Chemical Reaction Space at the Formation of Chalcogenidometalate Superspheres in Ionic Liquids

23 gennaio, 2017 - 00:00

Exploring the Chemical Reaction Space at the Formation of Chalcogenidometalate Superspheres in Ionic Liquids

Ionic liquids: The subtle influence of Cl− on the general observability as well as the crystal yield and quality of salts of the chalcogenidometalate supersphere anion [Ge24Sn36Se132]24− in ionothermal syntheses are presented, and are ascribed to lowering of the precursor's reactivity by complex equilibria. With Cl− as the major impurity of former “chloride-free” ionic liquid charges, many synthesis protocols in the literature might be questionable.

[Communication]
Silke Santner, Sivathmeehan Yogendra, Jan J. Weigand, Stefanie Dehnen
Chem. Eur. J., January 23, 2017, DOI: 10.1002/chem.201605988. Read article

Efficient Synthetic Routes to (±)-Hippolachnin A, (±)-Gracilioethers E and F and the Alleged Structure of (±)-Gracilioether I

23 gennaio, 2017 - 00:00

Efficient Synthetic Routes to (±)‐Hippolachnin A, (±)‐Gracilioethers E and F and the Alleged Structure of (±)‐Gracilioether I

Members of the family: The carbonyl group at the C-1 made the C-2 oxidation more difficult than otherwise. However, eventually the Pb(OAc)4/I2/80 °C conditions worked well where other conditions failed. The last step oxidation along with several other novel steps created a quick route to several members in the gracilioether family, including the alleged structure for gracilioether I.

[Communication]
Ze-Jun Xu, Yikang Wu
Chem. Eur. J., January 23, 2017, DOI: 10.1002/chem.201605776. Read article

<sup>13</sup>C NMR Spectroscopy of N-Heterocyclic Carbenes Can Selectively Probe σ Donation in Gold(I) Complexes

23 gennaio, 2017 - 00:00

13C NMR Spectroscopy of N‐Heterocyclic Carbenes Can Selectively Probe &#x3C3; Donation in Gold(I) Complexes

A call for solid-state NMR experiments: In a large set of charged and neutral N-heterocyclic carbene complexes of gold(I), it has been demonstrated that a specific component of the NMR chemical shift tensor of the carbenic carbon provides a selective measure of the &#x3C3; donation of the Dewar–Chatt–Duncanson bonding model.

[Full Paper]
Demian Marchione, Maria A. Izquierdo, Giovanni Bistoni, Remco W. A. Havenith, Alceo Macchioni, Daniele Zuccaccia, Francesco Tarantelli, Leonardo Belpassi
Chem. Eur. J., January 23, 2017, DOI: 10.1002/chem.201605502. Read article

“Trojan Horse” Effect in Photocatalysis–How Anionic Silver Impurities Influence Apparent Catalytic Activity

23 gennaio, 2017 - 00:00

“Trojan Horse” Effect in Photocatalysis–How Anionic Silver Impurities Influence Apparent Catalytic Activity

Small amount but a large impact: Identical photocatalysts showed severe differences in catalytic performance depending on utilization or avoidance of silver in the synthetic strategy.

[Communication]
Simon Kaufhold, Lydia Petermann, Dieter Sorsche, Sven Rau
Chem. Eur. J., January 23, 2017, DOI: 10.1002/chem.201605391. Read article

Free-Radical Carbo-Alkenylation of Olefins: Scope, Limitations and Mechanistic Insights

23 gennaio, 2017 - 00:00

 Scope, Limitations and Mechanistic Insights

Radical and fast: Free-radical carbo-alkenylation of electron-rich olefins has been studied, varying the substitution pattern on the alkene, the radical precursor and on the final sulfonyl acceptor. The scope and limitations of the process was established, and the reaction mechanism has been specified using selected dienes as radical clocks. It was shown that the reversible addition of the released sulfonyl group onto the olefin is important and should not be overlooked when using such processes.

[Full Paper]
Redouane Beniazza, Virginie Liautard, Clément Poittevin, Benjamin Ovadia, Shireen Mohammed, Frédéric Robert, Yannick Landais
Chem. Eur. J., January 23, 2017, DOI: 10.1002/chem.201605043. Read article

Ruthenium–Ruthenium-Bonded [Bis{corrolato-ruthenium(III)}]<sup><i>n</i></sup> (<i>n</i>=0, +1, −1) Complexes: Model Compounds for the Photosynthetic Special Pair

23 gennaio, 2017 - 00:00

 Model Compounds for the Photosynthetic Special Pair

Mimicking the special pair: A series of ruthenium–ruthenium-bonded dimeric corrole complexes has been prepared (see figure). Upon one-electron-oxidation of these complexes, the RuIII–RuIII situation is largely retained, and metal-bound corrolato radicals are generated. Two NIR bands at 1064 nm (LMCT-type) and 2315 nm (ILCT-type) are seen for a representative oxidized complex, which closely resemble those originating from the radical cations of the photosynthetic “special pair”.

[Full Paper]
Woormileela Sinha, Michael G. Sommer, Lara Hettmanczyk, Bratati Patra, Vasileios Filippou, Biprajit Sarkar, Sanjib Kar
Chem. Eur. J., January 23, 2017, DOI: 10.1002/chem.201604901. Read article

Tailoring Colors by O Annulation of Polycyclic Aromatic Hydrocarbons

23 gennaio, 2017 - 00:00

Tailoring Colors by O Annulation of Polycyclic Aromatic Hydrocarbons

Staring at the rainbow: &#x3C0;-extended O-doped polycyclic aromatic hydrocarbons were synthesized by high-yielding ring-closure reactions leading to the formation of furanyl or pyranopyranyl frameworks. Photophysical and electro chemical characterization showed that these compounds exhibit finely tunable optoelectronic properties (see figure), while third-order nonlinear optical measurements revealed very good second hyperpolarizability values, which make them exceptional candidates for photonic applications.

[Full Paper]
Tanja Mileti&#x107;, Andrea Fermi, Ioannis Orfanos, Aggelos Avramopoulos, Federica De Leo, Nicola Demitri, Giacomo Bergamini, Paola Ceroni, Manthos G. Papadopoulos, Stelios Couris, Davide Bonifazi
Chem. Eur. J., January 23, 2017, DOI: 10.1002/chem.201604866. Read article

Borinic Acid Catalysed Reduction of Tertiary Amides with Hydrosilanes: A Mild and Chemoselective Synthesis of Amines

23 gennaio, 2017 - 00:00

 A Mild and Chemoselective Synthesis of Amines

Unexpected reactivity: The boronic acid-catalysed reduction of tertiary amides with the use of hydrosilanes efficiently and chemoselectively led to the formation of several useful amines under very mild conditions. The procedure tolerates a variety of functional groups and may become a strong alternative to metal- and perfluoroborane-based reactions.

[Communication]
Aurélien Chardon, Tharwat Mohy El Dine, Rémi Legay, Michaël De Paolis, Jacques Rouden, Jérôme Blanchet
Chem. Eur. J., January 23, 2017, DOI: 10.1002/chem.201604802. Read article

Furan- and Thiophene-Based Auxochromes Red-shift Chlorin Absorptions and Enable Oxidative Chlorin Polymerizations

23 gennaio, 2017 - 00:00

Furan‐ and Thiophene‐Based Auxochromes Red‐shift Chlorin Absorptions and Enable Oxidative Chlorin Polymerizations

Stronger together: Chlorins carrying five-membered heterocycles in meso- and &#x3B2;-positions were prepared. Heterocycles in the 3- and 13-positions red-shift chlorin absorption and emission. Bis-thienylchlorins undergo oxidative electropolymerization, as well as co-polymerization with 3-hexylthiophene to yield red-absorbing polymers.

[Full Paper]
Ruisheng Xiong, Anna-Bea Bornhof, Anna I. Arkhypchuk, Andreas Orthaber, K. Eszter Borbas
Chem. Eur. J., January 23, 2017, DOI: 10.1002/chem.201604655. Read article

Synthesis of High-Purity Imidazolium Tetrafluoroborates and Bis(oxalato)borates

23 gennaio, 2017 - 00:00

Synthesis of High‐Purity Imidazolium Tetrafluoroborates and Bis(oxalato)borates

IL? Better! The synthesis and purification of imidazolium-based ionic liquids (ILs) with boron-containing anions is reported. It was possible to shorten the reaction and purification times, to avoid the use of acetonitrile as processing solvent, and to increase the yield compared to the known procedure for bis(oxalato)borate-containing ILs. Flashpoints of the ILs could be exactly determined by the continuously closed-cup flashpoint method.

[Communication]
Paulo Schmitz, Rene Jakelski, Kirsi Jalkanen, Martin Winter, Peter Bieker
Chem. Eur. J., January 23, 2017, DOI: 10.1002/chem.201604461. Read article

Metal–Organic Framework Supported on Processable Polymer Matrix by In Situ Copolymerization for Enhanced Iron(III) Detection

23 gennaio, 2017 - 00:00

Metal–Organic Framework Supported on Processable Polymer Matrix by In Situ Copolymerization for Enhanced Iron(III) Detection

Taming the MOF: An in situ copolymerization strategy was developed to load a predesigned metal–organic framework (MOF) onto a polymer matrix to afford a transparent and processable MOF–polymer composite with enhanced iron(III) ion detection (see figure).

[Full Paper]
Chun-Sen Liu, Min Chen, Jia-Yue Tian, Lei Wang, Min Li, Shao-Ming Fang, Xi Wang, Li-Ming Zhou, Zhuo-Wei Wang, Miao Du
Chem. Eur. J., January 23, 2017, DOI: 10.1002/chem.201604210. Read article

Ionic Liquids and Poly(ionic liquid)s for Morphosynthesis of Inorganic Materials

23 gennaio, 2017 - 00:00

Ionic Liquids and Poly(ionic liquid)s for Morphosynthesis of Inorganic Materials

Designer solvents and additives: Ionic liquids and poly(ionic liquid)s have demonstrated great potential as “designer solvents and additives” for advanced inorganic synthesis. This review surveys recent key progress in this exciting research field and speculates on possible future directions.

[Minireview]
Min-Rui Gao, Jiayin Yuan, Markus Antonietti
Chem. Eur. J., January 23, 2017, DOI: 10.1002/chem.201604191. Read article

Microarray Analysis of Antibodies Induced with Synthetic Antitumor Vaccines: Specificity against Diverse Mucin Core Structures

23 gennaio, 2017 - 00:00

 Specificity against Diverse Mucin Core Structures

Antibody mapping: A library of mucin glycopeptides was prepared for the evaluation of antibodies generated from synthetic vaccines and directed against tumor-associated mucin-1 glycoproteins. All antibody sera showed high reactivity to the tumor-associated saccharide structures on MUC1. Extensive glycosylation with branched core 2 structures, typically found on healthy cells, abolishes antibody recognition of the antisera, and suggests that all vaccine conjugates preferentially induce a tumor-specific humoral immune response.

[Full Paper]
Christian Pett, Hui Cai, Jia Liu, Björn Palitzsch, Manuel Schorlemer, Sebastian Hartmann, Natascha Stergiou, Mengji Lu, Horst Kunz, Edgar Schmitt, Ulrika Westerlind
Chem. Eur. J., January 23, 2017, DOI: 10.1002/chem.201603921. Read article

Multichromophoric Perylenediimide–Silicon Phthalocyanine–C<sub>60</sub> System as an Artificial Photosynthetic Analogue

23 gennaio, 2017 - 00:00

Multichromophoric Perylenediimide–Silicon Phthalocyanine–C60 System as an Artificial Photosynthetic Analogue

The persistence of charge separation? A silicon phthalocyanine has been asymmetrically appended with perylenediimide and fulleropyrrolidine moieties through different linking units (see figure). The optical, energy-transfer (ET), and electron-transfer (EnT) properties of the resulting triad have been investigated.

[Full Paper]
Luis Martín-Gomis, Francisco Peralta-Ruiz, Michael B. Thomas, Fernando Fernández-Lázaro, Francis D'Souza, Ángela Sastre-Santos
Chem. Eur. J., January 23, 2017, DOI: 10.1002/chem.201603741. Read article

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