- Synthesis, molecular docking, and evaluation of novel bivalent pyrazolinyl-1,2,3-triazoles as potential VEGFR TK inhibitors and anti-cancer agents
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Abstract: Investigations in the discovery of tyrosinase enzyme inhibitors have the potential to design novel anti-cancer drugs. A variety of novel bivalent pyrazolinyl triazoles 5–7 were synthesized and identified. The bis-acetyl triazole 3 was accomplish
- Abd-Rabou, Ahmed A.,Abdel-Wahab, Bakr F.,Bekheit, Mohamed S.
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- Click chemistry produces hyper-cross-linked polymers with tetrahedral cores
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Methane and adamantane based hyper-cross-linked polymers have been prepared by click chemistry reacting the corresponding tetraalkynes with 1,4-diazidobenzene. The adamantane based HCP proved to be very efficient for CO2 capture at low pressure
- Plietzsch, Oliver,Schilling, Christine I.,Grab, Tobias,Grage, Stephan L.,Ulrich, Anne S.,Comotti, Angiolina,Sozzani, Piero,Muller, Thierry,Braese, Stefan
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- New cyclic RGD peptides: Synthesis, characterization, and theoretical activity towards αvβ3 integrin
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Two new cyclic RGD peptides were prepared using a click chemistry approach. The linear RGDfV peptide was synthesized by solid-phase peptide synthesis using a 9-fluorenylmetoxicarbonyl (Fmoc) strategy and a 2-chlorotrityl chloride resin. After coupling 5-h
- Vila?a, Helena,Ferreira, Paula M.T.,Micaelo, Nuno M.
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Read Online
- Length-dependent conductance of conjugated molecular wires synthesized by stepwise "click" chemistry
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We report the preparation and electrical characterization of conjugated oligophenylenetriazole (OPT) wires having systematically varied lengths up to 10 nm. OPT wires were built from gold substrates using Cu(I)-catalyzed azide alkyne cycloaddition and cha
- Luo, Liang,Frisbie, C. Daniel
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Read Online
- Bis-ethynylphosphonamidates as an Modular Conjugation Platform to Generate Multi-Functional Protein- and Antibody-Drug-Conjugates
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Bis-ethynylphosphonamidates allow for a simple chemoselective addition of two thiol-containing modules in a row. We describe four such bis-electrophiles that carry different functional O-substituents with tunable hydrophilicity and enable further subseque
- Hackenberger, Christian P. R.,Helma, Jonas,Kasper, Marc-André,Lassak, Lukas,Mai, Isabelle,Schumacher, Dominik,Vogl, Annette M.
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supporting information
(2022/01/20)
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- Heterogeneous photocatalysis of azides: Extending nitrene photochemistry to longer wavelengths
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The photodecomposition of azides to generate nitrenes usually requires wavelengths in the 300 nm region. In this study, we show that this reaction can be readily performed in the UVA region (368 nm) when catalyzed by Pd-decorated TiO2. In aqueous medium the reaction leads to amines, with water acting as the H source; however, in non-protic and non-nucleophilic media, such as acetonitrile, nitrenes recombine to yield azo compounds, while azirine-mediated trapping occurs in the presence of nucleophiles. The heterogeneous process facilitates catalyst separation while showing great chemoselectivity and high yields.
- Argüello, Juan E.,Lanterna, Anabel E.,Lemir, Ignacio D.,Scaiano, Juan C.
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supporting information
p. 10239 - 10242
(2020/10/02)
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- Linear C2 symmetric compound, lanthanide polynuclear complex and preparation method and application of lanthanide polynuclear complex
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The invention discloses a linear C2 symmetric compound, a lanthanide polynuclear complex and a preparation method and application of the lanthanide polynuclear complex, and belongs to the field of photochemical supramolecules. The structural formula of the linear C2 symmetric compound is shown in the specification. The linear C2 symmetric compound is obtained by carrying out triazole cyclization reaction on an azide compound and an alkyne compound at the temperature of 50-70 DEG C. The lanthanide polynuclear complex has a general formula Ln2nL3n, wherein Ln is selected from lanthanide, L is anorganic ligand selected from the linear C2 symmetric compound, and n is selected from 1 or 2. The preparation method comprises the steps: carrying out a reaction on a lanthanide Ln precursor with theorganic ligand L at the temperature of 30-50 DEG C. The linear C2 symmetric compound comprises a triazole-pyridine-amide chelating group, can improve the efficiency of energy transfer from an intermediate chromophore of the ligand to a rare earth center, and improve the construction of a lanthanide complex having a high nuclear number, and thus the obtained complex having strong light-emitting properties and includes a lanthanide organic polyhedral cage having a high nuclear number.
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Paragraph 0112; 0121-0122
(2020/08/18)
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- Synthesis, structure, and synthetic potential of arenediazonium trifluoromethanesulfonates as stable and safe diazonium salts
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Aromatic diazonium salts are valuable building blocks for organic synthesis; however, in most cases, they are unstable, unsafe, poorly soluble, and/or expensive. In this paper, we have shown that a variety of stable and safe arenediazonium triflates ArN2+ TfO– can be obtained easily and in high yields by diazotization of anilines with tert-butyl nitrite in the presence of trifluoromethanesulfonic acid. Arenediazonium triflates are relatively shelf-stable in the dry state. They dissolve well in water, as well as polar and even nonpolar organic solvents. Less than 800 J/g of energy is released during the thermal decomposition of these salts, which indicates their explosion safety. Arenediazonium triflates have a high reactivity in the known reactions of diazonium chemistry, and undergo an unusual metal-free chlorodediazonization reaction with chloroform and CCl4.
- Filimonov, Victor D.,Krasnokutskaya, Elena A.,Kassanova, Assia Zh.,Fedorova, Valentina A.,Stankevich, Ksenia S.,Naumov, Nikolay G.,Bondarev, Alexander A.,Kataeva, Veronika A.
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supporting information
p. 665 - 674
(2018/09/14)
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- A green route for the cross-coupling of azide anions with aryl halides under both base and ligand-free conditions: Exceptional performance of a Cu2O-CuO-Cu-C nanocomposite
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A convenient, inexpensive and effective route for the preparation of a Cu2O-CuO-Cu-C nanocomposite is described here by applying Cu(ii) as a source of copper. Characterization of the nanocomposite was performed with X-ray diffraction (XRD), Fourier-transform infrared spectroscopy (FT-IR), transmission electron microscopy (TEM), high-resolution TEM (HR-TEM), field emission scanning electron microscopy (FE-SEM), X-ray photoelectron spectroscopy (XPS), and energy-dispersive X-ray spectroscopy (EDX). Analysis of the data showed that the particles of the nanocomposite are uniformly distributed and show high catalytic activity in the cross-coupling of sodium azide with various aryl iodides and bromides. This nanocomposite has a high level of performance, and even led to the synthesis of the products at room temperature. In addition, this is the first report of the synthesis of aryl azides under both base- and ligand-free conditions. For the first time, both ligand- and base-free conditions were applied for the synthesis of aryl azides, which implies exceptional performance of the Cu2O-CuO-Cu-C nanocomposite. Simultaneous removal of the base and ligand in a green solvent is the main advantage of this reaction. Unfortunately, aryl bromides and aryl iodides with electron-withdrawing functional groups in their scaffold did not give the desired aryl azides.
- Karimzadeh, Morteza,Niknam, Khodabakhsh,Manouchehri, Neda,Tarokh, Dariush
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p. 25785 - 25793
(2018/07/31)
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- Dual role of Cu2O nanocubes as templates and networking catalysts for hollow and microporous Fe-porphyrin networks
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Cu2O nanocubes were used for the synthesis of hollow and microporous Fe porphyrin networks (H-MFePN). In this synthesis, Cu2O nanocubes performed not only as networking catalysts but also as shape controlling templates. MFePN were formed on the surface of the Cu2O nanocubes through azide-alkyne cycloaddition of tetrakis(4-ethynylphenyl) Fe-porphyrin with 1,4-diazidobenzene. H-MFePN showed excellent catalytic activities in carbene insertion into N-H bonds, maintaining their activities during five recycle tests.
- Kang, Daye,Ko, Ju Hong,Choi, Jaewon,Cho, Kyoungil,Lee, Sang Moon,Kim, Hae Jin,Ko, Yoon-Joo,Park, Kang Hyun,Son, Seung Uk
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p. 2598 - 2601
(2017/03/09)
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- One pot synthesis of aromatic azide using sodium nitrite and hydrazine hydrate
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A simple, rapid, and efficient protocol for the synthesis of aryl azide using sodium nitrite and hydrazine hydrate at room temperature is discussed. The short reaction time, simple work-up procedure, and use of inexpensive reagents are advantages of this method.
- Siddiki, Afsar Ali,Takale, Balaram S.,Telvekar, Vikas N.
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p. 1294 - 1297
(2013/03/13)
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- Synthesis of conjugated hyperbranched polytriazoles containing truxene units by click polymerization
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It has been a challenge to synthesize high molecular weight and soluble conjugated hyperbranched poly(1,2,3-triazole)s (hb-PTAs). In this paper a series of soluble hyperbranched polytriazoles, whose number-average molecular weight (Mn) and poly
- Li, Dongzhi,Wang, Xin,Jia, Yutao,Wang, Aiqing,Wu, Yonggang
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experimental part
p. 861 - 868
(2012/06/16)
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- A highly selective and sensitive polymer-based fluorescence sensor for Hg2+-ion detection via click reaction
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Mercury rising: A Highly Selective and sensitive polymer-based fluorescence sensor synthesized using click reactions affords the most-pronounced fluorescence response to Hg2+ ions.
- Wu, Yuanzhao,Dong, Yu,Li, Junfeng,Huang, Xiaobo,Cheng, Yixiang,Zhu, Chengjian
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supporting information; experimental part
p. 2725 - 2729
(2012/06/15)
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- Synthesis and characterization of DMAP-modified NPY Y1 receptor antagonists as acyl-transfer catalysts
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Starting from the working hypothesis that specific chemical labelling may be an attractive approach to detect and study G protein-coupled receptors (GPCRs) we synthesized catalytically active antagonists of the neuropeptide Y1 receptor (Y1R). An argininamide-type Y1R antagonist scaffold was combined with a DMAP moiety via spacers of different length and chemical nature. These hybrid compounds have Y1R affinities in the two-digit nanomolar range and are capable of catalysing acyl-transfer reaction to surrogates of bionucleophiles, as demonstrated in the absence of cells by using esters of fluorescent dyes as substrates in buffer. By contrast, selective staining of Y1Rs on living MCF-7 cells was not achieved due to significant non-catalysed (Y1R ligand independent) reaction with biomolecules and the limited density of Y1R on the cell surface. Although this may also depend on insufficient selectivity of the staining reagents, the results of this study suggest that the general applicability of catalytic staining to GPCRs has to be reconsidered, as this approach is hampered by a very low portion of receptor of interest compared to the total amount of membrane proteins.
- Weiss, Stefan,Bernhardt, Guenther,Buschauer, Armin,Koenig, Burkhard
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experimental part
p. 763 - 780
(2011/12/04)
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- Triazole-pyridine ligands: A novel approach to chromophoric iridium arrays
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We describe a novel modular approach to a series of luminescent iridium complexes bearing triazole-pyridine-derived ligands that were conveniently prepared by using "click" chemistry. One, two or three triazole-pyridine units were effectively built into the heteroaromatic macromolecule using versatile acetylene- and azide-functionalised precursors. Using this approach, a series of iridium-derived molecules, that differ in the number of iridium centres, the structural characteristics of the cyclometalating ligand and the backbone, were synthesised. The preliminary photophysical properties of the prepared complexes indicate that there is only limited interaction (through space or through the backbone) between the iridium centres within one molecule and that each iridium centre retains its individual properties. The results show that our approach can be generally applied towards covalently linked multichromophoric systems with potential application, for instance, in the design and preparation of tunable light emitters. As a demonstration of this concept, a single molecule white-light emitter, constructed from two iridium centres (yellow emission) and a fluorene unit (blue emission), is presented. The Royal Society of Chemistry.
- Juriek, Michal,Felici, Marco,Contreras-Carballada, Pablo,Lauko, Jan,Bou, Sandra Rodriguez,Kouwer, Paul H. J.,Brouwer, Albert M.,Rowan, Alan E.
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supporting information; experimental part
p. 2104 - 2111
(2011/10/02)
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- Facile synthesis of σ-π Conjugated organosilicon polymers via Click polymerization
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Poly[silylene-(1,2,3-triazol-4-yl)-1,4-phenylene]s have been prepared via Cu(I)-catalyzed Azides and Alkynes Cycloaddition (CuAAC) polymerization from diethynylsilanes and 1,4-diazidobenzene. The organosilicon units contribute to electronic transitions be
- Wang, Yike,Wang, Dengxu,Han, Jianjun,Feng, Shengyu
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experimental part
p. 1874 - 1878
(2011/06/19)
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- Click polymerization: Synthesis of novel σ-π Conjugated organosilicon polymers
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Poly[silylene-1,4-phenylene-(1,2,3-triazol-4-yl)-1,4-phenylene]s were prepared via step-growth Click coupling polymerization of bis(p-ethynylphenyl) silanes and 1,4-diazidobenzene. The organosilicon units in the backbones may contribute to an electronic c
- Wang, Yike,Wang, Dengxu,Xu, Caihong,Wang, Rui,Han, Jianjun,Feng, Shengyu
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experimental part
p. 3000 - 3005
(2011/09/15)
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- Fluorescence polymer incorporating triazole and Benzo[2,1,3]thiadiazole moieties for Ni2+ detection
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Conjugated polymer could be obtained by the polymerization of 4,7-diethynylbenzo[2,1,3]thiadiazole (M-1) with 1,4-diazidobenzene (M-2) via click reaction. The polymer shows strong blue-green fluorescence due to the extended π-electronic structure in the m
- Huang, Xiaobo,Dong, Yu,Meng, Jie,Cheng, Yixiang,Zhu, Chengjian
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supporting information; experimental part
p. 1841 - 1844
(2010/10/02)
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- Polymer-based fluorescence sensor incorporating triazole moieties for Hg2+ detection via click reaction
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The polymer could be obtained by the polymerization of 1,4-dibutoxy-2,5-diethynylbenzene (M-1) with 1,4-diazidobenzene (M-2) via click reaction. The polymer show blue fluorescence. The responsive optical properties of the polymer on various transition metal ions were investigated by fluorescence spectra. Compared with other cations, such as Co2+, Ni2+, Ag+, Cd2+, Cu2+ and Zn2+, Hg2+ can exhibit the most pronounced fluorescence response of the polymer Hg2+ can exhibit the most pronounced fluorescence response of the polymer due to triazole moiety in the polymer main chain as the metal binding ligand. The results indicate this kind of conjugated polymer with triazole moiety synthesized by click reaction can be used as a selective fluorescence sensor for Hg2+ detection.
- Huang, Xiaobo,Meng, Jie,Dong, Yu,Cheng, Yixiang,Zhu, Chengjian
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scheme or table
p. 3064 - 3067
(2011/11/12)
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- Characterizing triplet states of quinonoidal dinitrenes as a function of conjugation length
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Photolysis of para,para'-diazide precursors in 2-methyltetrahydrofuran gives biradical ESR spectra assignable to quinonoidal dinitrenes with excited triplet biradical states. The zero field splitting (zfs) parameters for the biradicals at 77 K are as foll
- Minato, Masaki,Lahti, Paul M.
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p. 2187 - 2195
(2007/10/03)
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- Rates of thermolysis of azidobenzenes in solution: Large stabilizations of transition states by charge transfer from electron-donor substituents
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Introduction of +R type para substituents into azidobenzenes causes very large increases in rate of thermolysis, up to 225-fold. The rates of nitrobenzene solutions at 120°C follow a Hammett-type linear free energy relationship log k = -5.44 - 2.33σ1 - 1.48R+ which indicates conjugative stabilization of a nitrene-like transition state. ortho-Substituents of the +R type causes still larger rate enhancements, up to 456-fold for 2-amino, which identify a special resonance proximity effect. It is suggested that the very high rates reported for such α-azidoheterocycles as 2-azidothiophene are due to similar resonance stabilizations and not to ring-opening concerted with nitrogen loss.
- Dyall, Leonard K.,L'abbe, Gerrit,Dehaen, Wim
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p. 971 - 975
(2007/10/03)
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