- Efficient green coumarin dopants for organic light-emitting devices
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We have synthesized a new green fluorescent dopant C-545P having incorporated five strategically placed "methyl" steric spacers on the julolidyl ring system. C-545P has good thermal properties and photostability, and when fabricated as a dopant in an Alq3-hosted OLED device, it shows notable improvement in luminance efficiency and is more resistant to concentration quenching than C-545T, particularly in the doping concentration range between 1 and 2% v/v, while achieving comparable device stability.
- Lee, Meng-Ting,Yen, Chia-Kuo,Yang, Wen-Ping,Chen, Hsian-Hung,Liao, Chi-Hung,Tsai, Chih-Hung,Chen, Chin H.
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Read Online
- The synthesis and first full structural elucidation of a benzotriazole azo dye
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Although azo dyes containing benzotriazole are of interest as substrates for surface enhanced resonance Raman scattering, SERRS, little is known of their molecular structure due to their poor crystal growth properties. We recently synthesised a highly crystalline dihydroquinoline via an unusual condensation reaction and we report herein that the azo-benzotriazole dye subsequently formed was sufficiently crystalline to allow structural elucidation using synchroton radiation. It was found that this benzotriazole dye exists as the unexpected 6-isomer and the structure of the dihydroquinoline moiety changes markedly on coupling due to increased delocalisation.
- Graham,Kennedy,Teat
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Read Online
- 7-methoxy-2,2,4-trimethyl-1,2-dihydroquinoline
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The title compound, C13H17NO, was prepared using a new class of activator, alkyl bromides. The heterocyclic ring adopts a non-planar conformation, which contrasts with the conformations found for related compounds.
- Graham, Duncan,Kennedy, Alan R.
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Read Online
- Rhodamine analogs for molecular ruler applications
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A series of geometrically well-defined cationic fluorophores were designed based on molecular mechanics. They contain biaryl linkers to impart rigidity preventing intramolecular folding between a conjugated biomolecule and fluorophore. All probes have absorption and emission maxima within 20 nm from Texas Red, as predicted by TDDFT calculations and validated experimentally.
- Chu, Yu-Hsuan,Escobedo, Jorge O.,Jiang, Meiyan,Steyger, Peter S.,Strongin, Robert M.
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Read Online
- NEAR-INFRARED NERVE-SPARING FLUOROPHORES
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Provided are far red to near-infrared nerve-sparing fluorescent compounds, compositions comprising them, and methods of their use in medical procedures.
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Page/Page column 48
(2020/02/17)
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- Quinazoline Ligands Induce Cancer Cell Death through Selective STAT3 Inhibition and G-Quadruplex Stabilization
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The signal transducer and activator of transcription 3 (STAT3) protein is a master regulator of most key hallmarks and enablers of cancer, including cell proliferation and the response to DNA damage. G-Quadruplex (G4) structures are four-stranded noncanonical DNA structures enriched at telomeres and oncogenes' promoters. In cancer cells, stabilization of G4 DNAs leads to replication stress and DNA damage accumulation and is therefore considered a promising target for oncotherapy. Here, we designed and synthesized novel quinazoline-based compounds that simultaneously and selectively affect these two well-recognized cancer targets, G4 DNA structures and the STAT3 protein. Using a combination of in vitro assays, NMR, and molecular dynamics simulations, we show that these small, uncharged compounds not only bind to the STAT3 protein but also stabilize G4 structures. In human cultured cells, the compounds inhibit phosphorylation-dependent activation of STAT3 without affecting the antiapoptotic factor STAT1 and cause increased formation of G4 structures, as revealed by the use of a G4 DNA-specific antibody. As a result, treated cells show slower DNA replication, DNA damage checkpoint activation, and an increased apoptotic rate. Importantly, cancer cells are more sensitive to these molecules compared to noncancerous cell lines. This is the first report of a promising class of compounds that not only targets the DNA damage cancer response machinery but also simultaneously inhibits the STAT3-induced cancer cell proliferation, demonstrating a novel approach in cancer therapy.
- ?hlund, Daniel,Akhunzianov, Almaz,Br?nnstr?m, Kristoffer,Chand, Karam,Chorell, Erik,Deiana, Marco,Doimo, Mara,Hedenstr?m, Mattias,Jamroskovic, Jan,Kasho, Kazutoshi,Kumar, Rajendra,Mason, James E.,Medini, Paolo,Nath Das, Rabindra,Obi, Ikenna,Pourbozorgi, Parham L.,Sabouri, Nasim,Sulis Sato, Sebastian,Wanrooij, Sjoerd
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supporting information
(2020/02/13)
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- MADRASIN-DERIVATIVE COMPOUNDS, COMPOSITION AND USES THEREOF FOR TREATING CANCER
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The present invention relates to the fields of medicine and in particular cancer treatment. The invention more specifically relates to new compounds which are typically for use as a medicament. In particular, the invention relates to the use of these new compounds for increasing the presentation, typically the production and presentation, of Pioneer Translation Products (PTPs)-derived antigens by cells, in particular cancer cells, or changing the immunopeptidome, in a subject, and inducing or stimulating an immune response in the subject. The present disclosure also relates to uses of such compounds, in particular to prepare a pharmaceutical composition and/or to allow or improve the efficiency of a therapy in a subject in need thereof. The invention also discloses methods for treating a disease, in particular cancer, for preventing or treating cancer metastasis and/or cancer recurrence, in a subject. The present invention in addition provides kits suitable for preparing a composition according to the present invention and/or for implementing the herein described methods.
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Page/Page column 23
(2020/06/05)
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- COMPOUNDS TARGETING DUAL G-QUADRUPLEX DNA AND STAT3
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The present invention relates to novel quinazoline compounds having the formula (I) or (II): (I) (II). The compounds are active both as stabilizers of G-quadruplex DNA structures and as inhibitors of STAT3 phosphorylation. The disclosed compounds are useful in medical treatment, such as the treatment of cancer.
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Page/Page column 31; 34-35
(2021/01/23)
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- Fluorescence Compounds and Preparation Method Therof
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An object of the present invention is to provide a fluorescent compound which is excellent in fluorescence intensity, relative quantum efficiency, and a labeling ratio, thereby being able to be used as a contrast agent composition, and a labeling method using the same. The fluorescent compound according to the present invention is superior in terms of fluorescence intensity, relative quantum efficiency, and the labeling ratio, thereby being able to be effectively used for labeling and dyeing a target material. In addition, the fluorescent compound has excellent optical stability, thereby exhibiting stable fluorescence even for a long time of dyeing, and since the fluorescent compound has excellent fluorescence intensity without accumulation during administration to the body, it is possible to easily perform dyeing and in-vivo imaging even when a small amount of a dye is used compared to conventional dyes, thereby being economically available.(AA) Compound 1-3 (0.013 andmu;M)COPYRIGHT KIPO 2019
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Paragraph 0071-0075
(2019/08/26)
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- DIARYLETHER-BASED FLUOROGENIC PROBES FOR DETECTION OF HYPOCHLOROUS ACID OR HYDROXYL RADICAL
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Provided herein are improved fluorogenic compounds and probes that can be used as reagents for measuring, detecting and/or screening hypochlorous acid or hydroxyl radical. The fluorogenic compounds of the invention can produce fluorescence colors, such as green, yellow, red, or far-red. Also provided herein are fluorogenic compounds for selectively staining hypochlorous acid or hydroxyl radical in the mitochondria of living cells. Provided also herein are methods that can be used to measure, directly or indirectly, the presence and/or amount of hypochlorous acid or hydroxyl radical in chemical samples and biological samples such as cells and tissues in living organisms. Also provided are high-throughput screening methods for detecting or screening hypochlorous acid or hydroxyl radical or compounds that can increase or decrease the level of hypochlorous acid or hydroxyl radical in chemical and biological samples.
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Paragraph 0101; 0102
(2016/11/14)
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- The: P -toluenesulfonic acid catalyzed single pot synthesis of tetracyclic 1,2-dihydroquinolines: A metal free approach
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A simple, convenient and efficient p-toluenesulfonic acid catalyzed tandem reaction of aliphatic ketones with substituted anilines towards the synthesis of polysubstituted 1,2-dihydroquinolines has been developed. The ready availability of the catalyst, operational simplicity, cost effectiveness of the process and excellent regioselectivity mark some of the highlights of this methodology.
- Hajare, Anil K.,Jagdale, Arun R.,Shenoy, G. Gautham,Sinha, Neelima
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supporting information
p. 4888 - 4890
(2016/07/06)
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- MONOAZO DYES WITH CYCLIC AMINE AS FLUORESCENCE QUENCHERS
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The present disclosure provides reactive quencher dyes that can be used in the detection and/or quantification of desirable target molecules, such as proteins, nucleic acids and various cellular organelles. These dyes are essentially non-fluorescent but are efficient quenchers of various fluorescent dyes. Also, provided are methods of using the dyes, bio-probes incorporating dyes and methods of using the bio-probes. The quencher dyes described herein are modified to provide beneficial properties.
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Paragraph 0060
(2016/10/27)
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- The catalytic enantioselective synthesis of tetrahydroquinolines containing all-carbon quaternary stereocenters via the formation of aza-ortho-xylylene with 1,2-dihydroquinoline as a precursor
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Tetrahydroquinolines (THQs) with an all-carbon quaternary stereocenter were effectively obtained via the in situ formation of aza-ortho-xylylene (AOX) with easily accessible 1,2-dihydroquinolines as precursors. The reaction was rationalized with chiral phosporic acid to afford chiral THQs with high yield and excellent enantioselectivity.
- Li, Guangxun,Liu, Hongxin,Wang, Yingwei,Zhang, Shiqi,Lai, Shujun,Tang, Ling,Zhao, Jinzhong,Tang, Zhuo
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supporting information
p. 2304 - 2306
(2016/02/09)
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- Synthesis and Biological Evaluation of Cyclopentaquinoline Derivatives as Nonsteroidal Glucocorticoid Receptor Antagonists
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The steroidal glucocorticoid antagonist mifepristone has been reported to improve the symptoms of depression. We report the discovery of 6-(3,5-dimethylisoxazol-4-yl)-2,2,4,4-tetramethyl-2,3,4,7,8,9-hexahydro-1H-cyclopenta[h]quinolin-3-one 3d (QCA-1093) as a novel nonsteroidal glucocorticoid receptor antagonist. The compound displayed potent in vitro activity, high selectivity over other steroid hormone receptors, and significant antidepressant-like activity in vivo.
- Eda, Masahiro,Kuroda, Tomoko,Kaneko, Satoshi,Aoki, Yoshiyuki,Yamashita, Masami,Okumura, Chieko,Ikeda, Yoshitaka,Ohbora, Tomoko,Sakaue, Masaki,Koyama, Natsumi,Aritomo, Keiichi
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supporting information
p. 4918 - 4926
(2015/07/02)
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- Enantioselective Organocatalytic Transfer Hydrogenation of 1,2-Dihydroquinoline through Formation of Aza-o-xylylene
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A new way of forming the aza-o-xylylene with easily accessible 1,2-dihydroquinolines as precursor has been developed. The presence of an electron-donating group at the proper position of 1,2-dihydroquinoline was crucial for protonation of the alkene through dearomatization with a simple Bronsted acid. The in situ forming reactive intermediate was trapped with Hantzsch ester to afford tetrahydroquinolines in excellent yield and enantioselectivity.
- Li, Guangxun,Liu, Hongxin,Lv, Gang,Wang, Yingwei,Fu, Qingquan,Tang, Zhuo
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supporting information
p. 4125 - 4127
(2015/09/15)
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- Regioselective synthesis of 1,2-dihydroquinolines by a solvent-free MgBr2-catalyzed multicomponent reaction
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A highly efficient and regioselective synthesis of 1,2-dihydroquinolines via a multicomponent reaction between an aniline and two ketones is described. This reaction was catalyzed by magnesium bromide and carried out under solvent-free conditions. When the reaction was performed by using 3-substituted anilines and nonsymmetrically substituted ketones, principally a single product was found among the four expected regioisomers. A variety of anilines and ketones, including cyclic ketones, were evaluated providing a series of 1,2-dihydroquinolines with diverse substitution patterns. A study of the mechanism is discussed. There is evidence of the in situ formation of the imine as a result of the reaction between the aniline and one of the ketones, before annulation to the heterocyclic ring.
- Gutierrez, Rsuini U.,Correa, Hans C.,Bautista, Rafael,Vargas, Jose Luis,Jerezano, Alberto V.,Delgado, Francisco,Tamariz, Joaquin
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p. 9614 - 9626
(2013/10/22)
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- FLUORESCENT DYES
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Provided are various compounds comprising the formula Also provided are fluorescent dyes comprising the above compound. Additionally, a fluorescence energy transfer system is provided that comprises the above-described fluorescent dye and a second dye, wherein the second dye is capable of energy transfer with the fluorescent dye. Further provided is a kit for labeling a target molecule, where the kit comprises the above-described fluorescent dye with additional reagents useful for labeling the target molecule. Additionally provided is a target molecule labeled with the above-described fluorescent dye. A method of labeling a target molecule is also provided. The method comprises contacting reactive group Z of the above-described fluorescent dye with the target molecule such that reactive group Z reacts with the target molecule to form a covalent bond between reactive group Z and the target molecule. Also, another method of labeling a target molecule is provided. The method comprises contacting the above-described fluorescent dye, which further comprises a member of a binding pair, with the target molecule, where the target molecule comprises a second member of the binding pair.
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Paragraph 0087
(2013/04/13)
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- Rhodamine F: A novel class of fluorous ponytailed dyes for bioconjugation
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Incorporation of fluorous ponytails such as polyfluorinated alkyl residues (CH2)m(CF2)nCF3 leads to a novel class of bright rhodamine-based fluorescence dyes. These dyes combine the excellent photophysical properties of the frequently used rhodamine dyes with the unique features of "light" fluorous molecules. One of those features is the possibility to separate substances utilizing fluorous solid-phase extraction (F-SPE), which is based on the specific intermolecular interaction between fluorous compounds. Thus, molecules, which are labeled with these new dyes, are not only accessible to fluorescence experiments, but can also be easily purified (via so-called FluoroFlash columns) prior to use. The dyes were bound to a cell penetrating peptoid (polycationic oligo(N-substituted) glycine) on solid supports. These conjugates were purified with F-SPE before their photophysical and biological properties were investigated. The Royal Society of Chemistry 2013.
- K?lmel, Dominik K.,Rudat, Birgit,Braun, Delia M.,Bednarek, Christin,Schepers, Ute,Br?se, Stefan
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p. 3954 - 3962
(2013/07/05)
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- Co-sensitization of organic dyes for efficient dye-sensitized solar cells
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Novel cyanine dyes, in which a tetrahydroquinoline derivative is used as an electron donor and 1-butyl-5-carboxy-3, 3-dimethyl-indol-1-ium moiety is used as an electron acceptor and anchoring group, were designed and synthesized for application in dye-sensitized solar cells. The photovoltaic performance of these solar cells depends markedly on the molecular structure of the dyes in terms of the n-hexyl chains and the methoxyl unit. Retardation of charge recombination caused by the introduction of n-hexyl chains resulted in an increase in electron lifetime. As a consequence, an improvement of open-circuit photovoltage (V oc) was achieved. Also, the electron injection efficiencies were improved by the introduction of methoxyl moiety, which led to a higher short-circuit photocurrent density (Jsc). The highest average efficiency of the sensitized devices (η) was 5.6 % (Jsc=13.3 mA cm-2, Voc=606 mV, and fill factor FF=69.1 %) under 100 mW cm-2 (AM 1.5G) solar irradiation. All of these dyes have very high absorption extinction coefficients and strong absorption in a relatively narrow spectrum range (500-650 nm), so one of our organic dyes was explored as a sensitizer in co-sensitized solar cells in combination with the other two other existing organic dyes. Interestingly, a considerably improved photovoltaic performance of 8.2 % (Jsc=20.1 mA cm-2, Voc=597 mV, and FF=68.3 %) was achieved and the device showed a panchromatic response with a high incident photon-to-current conversion efficiency exceeding 85 % in the range of 400-700 nm. Sensitive dyes absorb it all: Co-sensitization of three spectrally complementary dyes on a TiO2 film in a well-designed sequence significantly improves the photovoltaic performance of the device, and an efficiency of 8.2 % is achieved. The devices demonstrate a panchromatic response with an incident photon-to-current conversion efficiency >80 % over the entire visible spectral region from 400 to 700 nm. Copyright
- Cheng, Ming,Yang, Xichuan,Li, Jiajia,Zhang, Fuguo,Sun, Licheng
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- Dye-sensitized solar cells based on a donor-acceptor system with a pyridine cation as an electron-withdrawing anchoring group
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New hemicyanine dyes (CM101, CM102, CM103, and CM104) in which tetrahydroquinoline derivatives are used as electron donors and N-(carboxymethyl)-pyridinium is used as an electron acceptor and anchoring group were designed and synthesized for dye-sensitized solar cells (DSSCs). Compared with corresponding dyes that have cyanoacetic acid as the acceptor, N-(carboxymethyl)-pyridinium has a stronger electron-withdrawing ability, which causes the absorption maximum of dyes to be redshifted. The photovoltaic performance of the DSSCs based on dyes CM101-CM104 markedly depends on the molecular structures of the dyes in terms of the n-hexyl chains and methoxyl. The device sensitized by dye CM104 achieved the best conversion efficiency of 7.0 % (Jsc=13.4 mA cm-2, Voc=704 mV, FF=74.8 %) under AM 1.5 irradiation (100 mW cm-2). In contrast, the device sensitized by reference dye CMR104 with the same donor but the cyanoacetic acid as the acceptor gave an efficiency of 3.4 % (Jsc=6.2 mA cm -2, Voc=730 mV, FF=74.8 %). Under the same conditions, the cell fabricated with N719 sensitized porous TiO2 exhibited an efficiency of 7.9 % (Jsc=15.4 mA cm-2, Voc=723 mV, FF=72.3 %). The dyes CM101-CM104 show a broader spectral response compared with the reference dyes CMR101-CMR104 and have high IPCE exceeding 90 % from 450 to 580 nm. Considering the reflection of sunlight, the photoelectric conversion efficiency could be almost 100 % during this region.
- Cheng, Ming,Yang, Xichuan,Li, Jiajia,Chen, Cheng,Zhao, Jianghua,Wang, Yu,Sun, Licheng
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supporting information
p. 16196 - 16202
(2013/02/23)
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- Synthesis of near-IR fluorescent oxazine dyes with esterase-labile sulfonate esters
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Near-IR oxazine dyes are reported that contain sulfonate esters which are rapidly cleaved by esterase activity to unmask highly polar anionic sulfonates. Strategies for the synthesis of these dyes included the development of milder dye condensation conditions with improved functional compatibility and the use of an alkyl halide that allows for the introduction of esterase-labile sulfonates without the need for sulfonation of the target molecule.
- Pauff, Steven M.,Miller, Stephen C.
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supporting information; experimental part
p. 6196 - 6199
(2012/01/06)
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- Antitrypanosomal activity of 1,2-dihydroquinolin-6-ols and their ester derivatives
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The current chemotherapy for second stage human African trypanosomiasis is unsatisfactory. A synthetic optimization study based on the lead antitrypanosomal compound 1,2-dihydro-2,2,4-trimethylquinolin-6-yl 3,5-dimethoxybenzoate (TDR20364, 1a) was undertaken in an attempt to discover new trypanocides with potent in vivo activity. While 6-ether derivatives were less active than the lead compound, several N1-substituted derivatives displayed nanomolar IC50 values against T. b. rhodesiense STIB900 in vitro, with selectivity indexes up to > 18000. 1-Benzyl-1,2-dihydro-2,2,4- trimethylquinolin-6-yl acetate (10a) displayed an IC50 value of 0.014 μM against these parasites and a selectivity index of 1700. Intraperitoneal administration of 10a at 50 (mg/kg)/day for 4 days caused a promising prolongation of lifespan in T. b. brucei STIB795-infected mice (>14 days vs 7.75 days for untreated controls). Reactive oxygen species were produced when T. b. brucei were exposed to 10a in vitro, implicating oxidative stress in the trypanocidal mode of action of these 1,2-dihydroquinoline derivatives.
- Fotie, Jean,Kaiser, Marcel,Delfín, Dawn A.,Manley, Joshua,Reid, Carolyn S.,Paris, Jean-Marc,Wenzler, Tanja,Maes, Louis,Mahasenan, Kiran V.,Li, Chenglong,Werbovetz, Karl A.
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experimental part
p. 966 - 982
(2010/08/06)
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- Red-emitting rhodamine dyes for fluorescence microscopy and nanoscopy
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Fluorescent markers emitting in the red are extremely valuable in biological microscopy since they minimize cellular autofluorescence and increase flexibility in multicolor experiments. Novel rhodamine dyes excitable with 630 nm laser light and emitting at around 660 nm have been developed. The new rhodamines are very photostable and have high fluorescence quantum yields of up to 80 %, long excited state lifetimes of 3.4 ns, and comparatively low intersystem-crossing rates. They perform very well both in conventional and in subdiffraction-resolution microscopy such as STED (stimulated emission depletion) and GSDIM (ground-state depletion with individual molecular return), as well as in single-molecule-based experiments such as fluorescence correlation spectroscopy (FCS). Syntheses of lipophilic and hydrophilic derivatives starting from the same chromophore-containing scaffold are described. Introduction of two sulfo groups provides high solubility in water and a considerable rise in fluorescence quantum yield. The attachment of amino or thiol reactive groups allows the dyes to be used as fluorescent markers in biology. Dyes deuterated at certain positions have narrow and symmetrical molecular mass distribution patterns, and are proposed as new tags in MS or LC-MS for identification and quantification of various substance classes (e.g., amines and thiols) in complex mixtures. High-resolution GSDIM images and live-cell STED-FCS experiments on labeled microtubules and lipids prove the versatility of the novel probes for modern fluorescence microscopy and nanoscopy.
- Kolmakov, Kirill,Belov, Vladimir N.,Bierwagen, Jakob,Ringemann, Christian,Mueller, Veronika,Eggeling, Christian,Hell, Stefan W.
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body text
p. 158 - 166
(2010/03/26)
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- Rhodamine spiroamides for multicolor single-molecule switching fluorescent nanoscopy
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The design, synthesis, and evaluation of new rhodamine spiroamides are described. These molecules have applications in optical nanoscopy based on random switching of the fluorescent single molecules. The new markers may be used in (co)localization studies of various objects and their (mutual) positions and shape can be determined with a precision of a few tens of nanometers. Multicolor staining, good photoactivation, a large number of emitted photons, and selective chemical binding with amino or thiol groups were achieved due to the presence of various functional groups on the rhodamine spiroamides. Rigidized sulfonated xanthene fragment fused with six-membered rings, N,N′-bis(2,2,2-trifluoroethyl) groups, and a combination of additional double bonds and sulfonic acid groups with simple aliphatic spiroamide residue provide multicolor properties and improve performance of the rhodamine spiroamides in photoactivation and bioconjugation reactions. Having both essential parts of the photoswitchable assembly - the switching and the fluorescent (reporter) groups - combined in one chemical entity make this approach attractive for further development. A series of rhodamine spiroamides is presented along with characterizations of their most relevant properties for application as fluorescent probes in single-molecule switching and localization microscopy. Optical images with resolutions on the nanometer scale illustrate the potential of the labels in the colocalization of biological objects and the two-photon activation technique with optical sectioning.
- Belov, Vladimir N.,Bossi, Mariano L.,Foelling, Jonas,Boyarskiy, Vadim P.,Hell, Stefan W.
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experimental part
p. 10762 - 10776
(2010/04/05)
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- CONDENSED TETRAHYDROQUINOLINE DERIVATIVE AND USE THEREOF FOR MEDICAL PURPOSES
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The problem of the present invention is to provide a compound having a GR selective binding activity, which shows less action on other nuclear receptors such as progesterone receptor (PR), mineralocorticoid receptor (MR) and the like. The present invention provides a condensed tetrahydroquinoline compound represented by the following formula (I) wherein each symbol is as defined in the present specification, or a pharmaceutically acceptable salt thereof or a hydrate thereof.
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Page/Page column 53
(2009/12/05)
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- Scope and mechanistic study of the ruthenium-catalyzed ortho-C-H bond activation and cyclization reactions of arylamines with terminal alkynes
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The cationic ruthenium hydride complex [(PCy3) 2(CO)(CH3CN)2RuH]+BF 4- was found to be a highly effective catalyst for the C-H bond activation reaction of arylamines and terminal alkynes. The regioselective catalytic synthesis of substituted quinoline and quinoxaline derivatives was achieved from the ortho-C-H bond activation reaction of arylamines and terminal alkynes by using the catalyst Ru3-(CO)12/HBF 4·OEt2. The normal isotope effect (k CH/kCD = 2.5) was observed for the reaction of C 6H5NH2 and C6D5NH 2 with propyne. A highly negative Hammett value (ρ = -4.4) was obtained from the correlation of the relative rates from a series of meta-substituted anilines, m-XC6H4NH2, with σp in the presence of Ru3(CO)12/ HBF4·OEt2 (3 mol % Ru, 1:3 molar ratio). The deuterium labeling studies from the reactions of both indoline and acyclic arylamines with DC≡CPh showed that the alkyne C-H bond activation step is reversible. The crossover experiment from the reaction of 1-(2-amino-1-phenyl)pyrrole with DC≡CPh and HC≡CC6H4-p-OMe led to preferential deuterium incorporation to the phenyl-substituted quinoline product. A mechanism involving rate-determining ortho-C-H bond activation and intramolecular C-N bond formation steps via an unsaturated cationic ruthenium acetylide complex has been proposed.
- Yi, Chae S.,Yun, Sang Young
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p. 17000 - 17006
(2007/10/03)
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- Fluorescent probe for magnesium ion determination
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A fluorescent probe for measuring magnesium ion, which can selectively form a complex with magnesium ion in aqueous system is disclosed. The fluorescent probe for measuring magnesium ion according to the present invention has the structure represented by the following Formula [I]: 1(wherein R1 represents a hydrogen atom, metal atom or an ester-forming group; A represents a group which forms a ring structure together with carbon atom 1 and carbon atom 2; and X is a fluorescent group which may form a condensed ring together with the ring containing the group A).
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- Rhodamine derivatives and the use thereof
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The invention concerns rhodamine derivatives of the general formulae in which Ca-Cd each denote a C atom, and Ca and Cb as well as Cc and Cd are either linked together by a single bond or by a double bond; X1 to X16 denote independently of one another halogen, sulfonic acid, hydrogen or an alkyl residue with 1-20 C atoms in which the alkyl residue can be substituted with one or several halogen or sulfonic acid residues; R1 and R2 are either identical or different and denote either hydrogen, alkyl with 1-20 C atoms, polyoxyhydrocarbyl units, phenyl or phenylalkyl with 1-3 carbon atoms in the alkyl chain in which the alkyl and/or phenyl residues can be substituted by one or several hydroxy, halogen, sulfonic acid, amino, carboxy or alkoxycarbonyl groups where alkoxy can have 1-4 carbon atoms, R1 contains at least one activatable group, R2 and X4 can be optionally linked together via a bridge composed of 0-2 C atoms. In contrast to the prior art, these compounds are characterized in that A1, A2 and A3 can independently of one another denote hydrogen, cyano, halogen and sulfonic acid; B1 denotes either halogen, cyano or hydrogen; B2 denotes hydrogen, amide, halogen and an alkyl residue with 1-20 C atoms. In addition the invention concerns activated rhodamine derivatives, correspondingly conjugated biomolecules and their use in diagnostic systems.
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- Substitution Reaction of Tetracyanoethylene with Acetone-Anils
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The products from the condensation of acetone-anils (1) and TCNE reaction were characterized after separation. The main products, tricyanoethylene derivatives (7-9) were isolated with the malonodinitrile derivatives (10-12), respectively. The [2+2] cycloaddition product (13), namely 5-methoxy-3,4-(2′,2′,3′,3′-tetracyanocyclobutano)-1,2- dihydro-2,2,4-trimethylquinoline also has been isolated. The distribution of these three products is substituent dependent.
- Lin, Wen-Chung,Huang, Shing-Ting,Lin, Shaw-Tao
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p. 497 - 501
(2007/10/03)
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