- Synthesis and biological evaluation of pyridinium-functionalized carbazole derivatives as promising antibacterial agents
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Various pyridinium-functionalized carbazole derivatives were constructed by coupling the key fragments of carbazole skeleton and pyridinium nucleus in a single molecular architecture. Antibacterial bioassays revealed that some of the title compounds displ
- Wang, Pei-Yi,Fang, He-Shu,Shao, Wu-Bin,Zhou, Jian,Chen, Zhuo,Song, Bao-An,Yang, Song
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- Photoinduced intramolecular electron transfer between carbazole and bis(trichloromethyl)-s-triazine generating radicals
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An intramolecular electron transfer and photosensitivity in dye/initiator systems, in which an electron donating light-absorbing unit (carbazole) is tethered by methylene bonds to an electron-deficient initiator [bis-(trichloromethyl)-s-triazine], was investigated. The efficient quenching of fluorescence was observed in the tethered compounds in a rigid matrix at low temperature, and the higher sensitivity of photopolymerization was observed in the photopolymer films containing the tethered compounds as photoinitiating systems compared with the films containing physical mixtures of dye and initiator. The compounds tethered by a longer methylene chain (C6 and C11) showed a higher photosensitivity than that tethered by a shorter methylene chain (C2 and C3), despite the efficient fluorescence quenching in the latter compounds. Control of back electron transfer after initial electron transfer or control of radiationless deactivation via exciplex formation was suggested to be important factor to design efficient dye-linked photoinitiators.
- Kawamura, Koichi,Aotani, Yoshimasa,Tomioka, Hideo
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- Synthesis and polymerisation of novel methacrylates with carbazolyl and benzofuranyl pendant groups for photovoltaic applications
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This article reports properties of photovoltaic devices containing new donor materials - copolymers referred as PCEMB, composed of 2-(carbazol-9-yl) ethyl methacrylate (CEM) and benzofuran-2-carboxylic acid 2-(2- methylacryloyloxy)ethyl ester (MB). Manufactured photovoltaic cells consisted of donor and acceptor (PBT or P3OT) layers sandwiched between ITO covered glass and evaporated aluminum electrode. Performance of the cell was optimized for a copolymer composed of 8% CEM and 92% MB. The efficiency, found equal c.a. =0,03%, was low comparing to other photovoltaic cells reported in the literature. However, following the observed tendencies, it can be supposed that there exists a large reserve for the enhancement of the open circuit voltage through further chemical modifications of the chromophore. In the case of the PDT containing cells, measured Uoc was substantially lower. This fact may be attributed to difference in carrier mobility between this polymer and PCEMB. Simultaneously, the larger sizes of the MB molecule may favor separation of the charges and leads to enhancement of the corresponding voltage.
- Pokladko,Sanetra,Gondek,Bogdal,Niziol,Kityk
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p. 335/[701]-344/[710]
(2008)
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- FRET-based acrylic nanoparticles with dual-color photoswitchable properties in DU145 human prostate cancer cell line labeling
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Dual-color photoswitchable fluorescent polymer nanoparticles have emerged as an important type of cell detectors. Here, dual-color acrylic nanoparticles containing spiropyran and azo-carbazole derivatives with remarkable photostability and photoreversibility were employed. These prominent properties were attributed to the covalent bonding between the incorporated chromophores and the polymeric matrix and provided efficient fluorescence resonance energy transfer phenomenon. The obtained nanoparticles were purified after dialysis and delivered into DU145 cancer cells. Trypan blue dye exclusion assays showed that these nanoparticles were biocompatible with no toxicity to the cells. Fluorescence microscopy images demonstrated that the prostate cancer cells containing nanoparticles exhibited excellent cell uptake with green and red fluorescence emissions after primary excitation at 410?nm and subsequent irradiation at 365?nm, respectively, depicting their dual-color characteristics.
- Keyvan Rad, Jaber,Mahdavian, Ali Reza,Khoei, Samideh,Janati Esfahani, Azam
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- Synthesis and Morphology of Two Carbazole-Pyrazoline-Containing Polymer Systems and Their Electrical Memory Performance
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A new atom-transfer radical polymerization (ATRP) initiator 4-[1-(2-dodecyl-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)-3-(4-nitrophenyl)-4,5-dihydro-1H-pyrazol-5-yl]phenyl 2-bromo-2-methylpropanoate (IN) as an electron acceptor (A) and a monomer 2-(9H-carbazole-9-yl)-ethyl methacrylate (MCz) as an electron donor (D) were simultaneously introduced into two different D-A polymer systems by using the end-functionalizing or blending method. The mass percentage of IN in the end-functionalized polymer PMCz-IN and the mixed polymer composite PMCz+IN were both controlled at approximately 1.0wt. The optical, electrochemical, and surface morphology properties of the two polymeric films prepared by means of spin-coating technology were comparatively investigated. Sandwich devices based on PMCz-IN and PMCz+IN demonstrated nonvolatile write-once-read-many-times memory (WORM) and volatile static random access memory (SRAM) characteristics, respectively, which were further verified by the Kelvin probe force microscopy (KPFM) measurements. The proposed memory mechanism could be attributed to the formation of a stable charge-transfer (CT) complex for PMCz-IN and an unstable CT complex for PMCz+IN. Furthermore, the different distribution of IN in the two polymeric films might be the main reason for the stability of the CT complex.
- Lu, Cai-Jian,Li, Hua,Xu, Qing-Feng,Xu, Qing-Hua,Lu, Jian-Mei
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- Neutral state colorless electrochromic polymer networks: Spacer effect on electrochromic performance
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A series of carbazole-based monomers and their corresponding polymers with various spacer units were synthesized and coated onto ITO-glass surface via an electrochemical cross-linking process. All carbazole-based polymers exhibited multi-electrochromic be
- Gulfidan, Damla,Sefer, Emre,Koyuncu, Sermet,Acar, Metin H.
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- Palladium-based micellar nanohybrids: Preparation and nonlinear optical response
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In the present work the synthesis and physicochemical characterisation of a new class of Pd-containing micellar nanohybrid systems are presented. The new systems consist of metallic Pd nanoparticles and well-defined diblock copolymers, possessing carbazole and β-ketoester side-chain functionalities, namely poly[2-(N-carbazolyl) ethyl methacrylate]-block-poly[2- (acetoacetoxy) ethyl methacrylate] (CbzEMAx-b-AEMAy). Block copolymer synthesis has been carried out by Reversible Addition-Fragmentation chain Transfer (RAFT) polymerisation. The presence of the β-ketoester groups within these diblock copolymers enabled the complexation and stabilisation of the Pd nanoparticles in tetrahydrofuran. Visualisation of the Pd-containing micellar nanohybrids was realised by means of transmission electron microscopy (TEM), providing information on the metal nanoparticle sizes. The nonlinear optical response of these polymer-metal nanohybrid systems has been systematically studied both in solution and in thin films, using the Z-scan technique, employing 35 ps, visible (532 nm) and infrared (1064 nm) laser excitation. Discussion in regards to the spectral position of the surface plasmon resonance (SPR) of the Pd nanoparticles and its effect on the nonlinear optical response of the micellar systems has been carried out in terms of a two-photon process. The Royal Society of Chemistry.
- Papagiannouli, Irene,Demetriou, Maria,Krasia-Christoforou, Theodora,Couris, Stelios
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- Synthesis and photoluminescent property of star polymers with carbzole pendent and a zinc porphyrin core by ATRP
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Styrene-type monomer 9-(4-vinylbenzyl)-9H-carbazole (VBCz) and methacrylate-type monomer 2-(9Hcarbazole- 9-yl)-ethyl methacrylate (CzEMA) were polymerized to star polymers respectively via atom transfer radical polymerization (ATRP) using zinc 5,10,15,20-
- Tao, Yongxin,Xu, Qingfeng,Li, Najun,Lu, Jianmei,Wang, Lihua,Xia, Xuewei
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- The Effect of Random and Block Copolymerization with Pendent Carbozole Donors and Naphthalimide Acceptors on Multilevel Memory Performance
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Polymeric materials have been widely used in the fabrication of data-storage devices, owing to their unique advantages and defined conduction mechanisms. To date, the most-functional polymers that have been reported for memory devices were synthesized through random copolymerization, whilst there have been no reports regarding the memory effect of block polymers. Herein, we synthesized a random copolymer (PMCz8-co-PMBNa2) and its corresponding block copolymer (PMCz8-b-PMBNa2) to study the effect of the method of polymerization on the memory properties of the corresponding devices. Interestingly, both devices (ITO/PMCz8-co-PMBNa2/Al and ITO/PMCz8-b-PMBNa2/Al) exhibited ternary memory performance, with threshold voltages of ?1.7 V/?3.3 V and ?2.7 V/?3.8 V, respectively. However, based on comprehensive measurements, the memory properties of PMCz8-co-PMBNa2 and PMCz8-b-PMBNa2 were found to be owing to the operation of different conduction mechanisms, which resulted from different molecular stacking in the film state. Therefore, we expect that this work will be helpful for improving our understanding of the conduction mechanisms in polymer-based data-storage devices.
- Zhang, Qi-Jian,Zhou, Jia-Hui,Li, Hui,He, Jing-Hui,Li, Na-Jun,Xu, Qing-Feng,Chen, Dong-Yun,Li, Hua,Lu, Jian-Mei
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- Phosphorescence Spectroscopy for Poly and Its Copolymers with Methyl Methacrylate
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Our research project concerned to triplet spectroscopy of 3,6-dibromocarbazole chromophores in a methacrylate copolymer, poly.Owing to the "heavy atom effect" on the rate of singlet-triplet intersystem crossing, the phosphorescence spectra were clearly observed in a wide range of copolymer compositions.Although the triplet interaction between chromophores was weak in 2-methyltetrahydrofuran rigid glass, the copolymer films showed an alteration in spectra from the monomer to the triplet excimer emission with increasing chromophore concentration.The substituted bromine atoms provided a longer interaction distance between chromophores, and a weaker stabilization of energy at the excimer state, compared with unsubstituted carbazole.These effects were interpreted in terms of the extended electron cloud and the bulkiness of bromine atoms.
- Wada, Yoshio,Ito, Shinzaburo,Yamamoto, Masahide
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- Electron-Transfer Quenching Accompanied by Highly Efficient Energy Migration in Polymer Langmuir-Blodgett Films
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Copolymers of N-dodecylacrylamide (DDA), which has the excellent property to form LB film, and 2-(9-carbazolyl)ethyl acrylate (CzEA) with various copolymer compositions were prepared to investigate the electron transfer quenching of the excited carbazole chromophore in LB film assembly.The copolymers form a stable condensed monolayer and LB film in a wide range of copolymer compositions.In LB films, the emission spectra show only the structured emission characteristic of the monomeric carbazole chromophore at 350 nm and no excimer emission whereas the corresponding N-vinylcarbazole copolymer LB films in the previous study show strong emision from excimer which acts as an energy trapping site.For the quenching study, the DDA-CzEA monolayer are in direct contact with the mixed monolayer of barius stearate and stearyl viologen quencher.The emission of the excited carbazole was quenched effectively by a small amount of the viologen quencher in the mixed monolayer.The quenching efficiency was varied linearly by the mole fraction of carbazole chromophore in the copolymer monolayer.The effective electron-transfer quenching is attributed to the highly efficient energy migration between carbazole chromophores, which is assisted with a regular alignment of carbazole chromophore and no excimer formation in the copolymer LB films.The plots of ln(I0/I-1) (I in the presence of and I0 in the absence of the quencher) vs distance (R) between the quenchers gave a linear relationship.The mechanism of electron transfer quenching in the LB film assembly is discussed on the basis of electron-tunneling and energy migration.
- Yatsue, Toru,Miyashita, Tokuji
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- FRET Phenomenon in Photoreversible Dual-Color Fluorescent Polymeric Nanoparticles Based on Azocarbazole/Spiropyran Derivatives
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Incorporation of chromophores into a polymer chain results in prominent photoreversibility and fatigue resistance, photostability over the long term, and restriction of the internal conversion (IC). Here, we report the copolymerization of two photoactive monomers with methyl methacrylate via emulsion polymerization in order to obtain photoswitchable dual-color fluorescent nanoparticles. For this purpose, azocarbazole ethyl acrylate (AzoCzEA) and spiropyran ethyl acrylate (SPEA) were synthesized and the fluorescence polymeric latex nanoparticles were prepared correspondingly. FT-IR and 1HNMR spectra were used to confirm the structure of novel fluorescent AzoCzEA. UV-vis studies of the obtained nanoparticles displayed the spectral features of both AzoCzEA and SPEA under stimuli-irradiation and inclusion of these chromophores into the polymer particles. DSC analysis revealed an increase in Tg of the prepared copolymer, indicating covalently incorporation of the photoactive monomers into the polymer chains. The optimum ratio of two chromophores to achieve complete quenching and highest energy transfer was determined by UV-vis spectroscopy. DLS and SEM results demonstrated particle size distribution of 40-80 nm with spherical morphology. Fluorescence spectra revealed remarkable fluorescence resonance energy transfer (FRET) from AzoCzEA to SPEA after UV irradiation at 365 nm and dual-color characteristic of the prepared nanoparticles. Besides, an enhancement in the photoreversibility, photostability, prevention of IC, dye leakage, and aggregation were studied elaborately. The obtained results were attributed to the involvement of such chromophores into the polymeric matrix via covalent bonding. Labeling and tracking of living cells and rewriteable patterning are potential applications for such dual-color fluorescent nanoparticles.
- Keyvan Rad, Jaber,Mahdavian, Ali Reza,Salehi-Mobarakeh, Hamid,Abdollahi, Amin
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- Well-defined fluoro- and carbazole-containing diblock copolymers: Synthesis, characterization and immobilization onto Au-coated silicon surfaces
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A series of well-defined diblock copolymers consisting of 2-(N-carbazolyl)ethyl methacrylate (CbzEMA) and 2,2,3,3,4,4,4-heptafluorobutyl methacrylate (HFBMA) (CbzEMAx-b-HFBMAy) was synthesized by Reversible Addition-Fragmentation chain Transfer (RAFT) polymerization. All polymers were characterized in terms of molecular weights, molecular weight distributions and chemical compositions using Size Exclusion Chromatography (SEC), Fourier Transform Infrared (FTIR) spectroscopy and Proton Nuclear Magnetic Resonance (1H NMR) spectroscopy, respectively. The thermal properties (glass transition and decomposition temperatures) of the CbzEMAx and HFBMAx homopolymers and the CbzEMAx-b-HFBMAy diblock copolymers were determined by Differential Scanning Calorimetry (DSC) and Thermal Gravimetric Analysis (TGA). As demonstrated by photoluminescence measurements, immobilization of the dithioester-ended functionalized CbzEMAx-b-HFBMAy chains onto Au-coated silicon surfaces has been accomplished via anchoring of the sulfur-containing end-groups onto the Au surfaces. The presence of the low-surface energy fluorinated block, combined with the electro-active carbazole-containing segment within CbzEMAx-b-HFBMAy diblock copolymers imparts to these immobilized thin layers useful properties towards their potential applicability in gas sensing technologies.
- Savva, Ioanna,Demetriou, Maria,Othonos, Andreas,Turcu, Rodica,Popa, Adriana,Macavei, Sergiu,Krasia-Christoforou, Theodora
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- Synthesis, structure, and biological evaluation of a platinum-carbazole conjugate
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Cisplatin resistance is caused, in part, by the efficient removal of the helix-distorting cisplatin 1,2-intrastrand cross-links by nucleotide excision repair (NER) machinery. To make a platinum-DNA adduct that causes less helical distortion than the cisplatin 1,2-intrastrand adduct, we designed and synthesized a monofunctional platinum-carbazole conjugate (carbazoplatin). The 2.5?? crystal structure of carbazoplatin-DNA adduct revealed both the monoplatination of the N7 of a guanine (G) base and the intercalation into two G:C base pairs, while causing a minor distortion of the DNA helix. A 50-mer dsDNA containing a single carbazoplatin lesion was poorly processed by UvrABC endonuclease, the prokaryotic NER machinery that detects helical distortion and performs dual incision around the lesion. Our cell viability assay indicated that the cytotoxic pathways of carbazoplatin might be different from those of cisplatin; carbazoplatin was 5–8 times more cytotoxic than cisplatin against PANC-1 and MDA-MB-231 cancer cell lines.
- Cheun, Young,Koag, Myong-Chul,Naguib, Youssef W.,Ouzon-Shubeita, Hala,Cui, Zhengrong,Pakotiprapha, Danaya,Lee, Seongmin
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- Carbazole modified oligonucleotides: Synthesis, hybridization studies and fluorescence properties
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Synthesis of the novel thiophenyl carbazole phosphoramidite DNA building block 5 was accomplished in four steps using a Suzuki-Miyaura cross-coupling reaction from the core carbazole and it was seamlessly accommodated into a 9-mer DNA-based oligonucleotide by incorporation at the flanking 5′-end in combination with a central insertion of an LNA-T nucleotide. The carbazole-containing oligonucleotide was combined in different duplex hybrids, which were characterized by thermal denaturation, circular dichroism and fluorescence studies. The carbazole monomer modulates the duplex stability in various ways. Thus, monomer Z increased the thermal stability of the 9-mer towards the complementary 9-mer/15-mer DNA duplex by 4.2 °C. Furthermore, indications of its intercalation into the duplex were obtained by modeling studies and robust decreases in fluorescence emission intensities upon duplex formation. In contrast, no clear intercalating tendency was corroborated for monomer Z within the DNA/RNA hybrid duplex as indicated by moderate quenching of the fluorescence and similar duplex thermal stabilities relative to the corresponding control duplex. The recognition efficiencies of the carbazole modified oligonucleotide toward single nucleotide mismatches were studied with two 15-mer model targets (DNA and RNA). For both systems, mismatches positioned at the juxtaposition of the carbazole monomer showed pronounced deceases in thermal denaturation temperature. Steady-state fluorescence emission studies of all mismatched duplexes with incorporation of Z monomer typically displayed efficient fluorescence quenching.
- Gouda, Alaa S.,J?rgensen, Per T.,Przypis, ?ukasz,Walczak, Krzysztof,Wengel, Jesper
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- Adjustment of conformation change and charge trapping in ion-doped polymers to achieve ternary memory performance
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Ion-doped poly(4-vinylpyridine) derivatives (P4VPCz), where in the pendant chains the electron-withdrawing pyridine moiety and acceptor carbazole moiety are linked by a flexible alkyl spacer were designed and synthesized. Sandwiched ITO/P4VPCz/Al devices, made through simple spin-coating processes have shown that they could be tuned from a binary to ternary memory performance, by increasing the carbazole content. P4VPCz2 with a 20% mole ratio of the carbazole moiety shows a binary performance according to the charge trapping of the pyridine acceptor in the polymer, while P4VPCz5 which contains a 50% mole ratio of carbazole in the pendant chains, exhibits a ternary data storage ability, probably induced by double mechanisms (i.e. a conformational change and charge trapping). Interestingly, as the carbazole mole ratio reached 80%, the polymer P4VPCz8 has a high conductivity state, with no switching behavior, because of the large amount of doped ions improving the charge transfer mobility. Thus, we hope can offer a guideline to achieve a high-performance multilevel memory material, via combining different mechanisms as well as doping ions.
- He, Dongwei,Zhuang, Hao,Liu, Haifeng,Liu, Hongzhang,Li, Hua,Lu, Jianmei
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- Aza-Matteson Reactions via Controlled Mono-and Double-Methylene Insertions into Nitrogen-Boron Bonds
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Boron-homologation reactions represent an efficient and programmable approach to prepare alkylboronates, which are valuable and versatile synthetic intermediates. The typical boron-homologation reaction, also known as the Matteson reaction, involves formal carbenoid insertions into C-B bonds. Here we report the development of aza-Matteson reactions via carbenoid insertions into the N-B bonds of aminoboranes. By changing the leaving groups of the carbenoids and altering Lewis acid activators, selective mono- and double-methylene insertions can be realized to access various α- and β-boron-substituted tertiary amines, respectively, from common secondary amines. The derivatization of complex amine-containing bioactive molecules, diverse functionalization of the boronate products, and sequential insertions of different carbenoids have also been achieved.
- Xie, Qiqiang,Dong, Guangbin
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p. 14422 - 14427
(2021/09/29)
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- Photo-induced phosphorescence and mechanoluminescence switching in a simple purely organic molecule
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A simple organic molecule, 2-(9H-carbazol-9-yl)ethanol (CZEO), displays both mechanoluminescence (ML) and photo-induced room-temperature phosphorescence (RTP). The D-A type dimer formed in the crystals was found to play a crucial role in the light-stimulated luminescent response, responsible for the turn-on RTP and turn-off ML switching of CZEO.
- Huang, Qiuqin,Mei, Xiaofei,Xie, Zongliang,Wu, Duobin,Yang, Shuming,Gong, Wenjing,Chi, Zhenguo,Lin, Zhenghuan,Ling, Qidan
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supporting information
p. 2530 - 2534
(2019/03/08)
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- Optimization of the metabolic stability of a fluorinated cannabinoid receptor subtype 2 (CB2) ligand designed for PET studies
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The central CB2 receptor represents a promising target for the treatment of neuroinflammatory diseases as CB2 activation mediates anti-inflammatory effects. Recently, the F-18 labeled PET radiotracer [18F]7a was reported,
- Heimann, Dominik,B?rgel, Frederik,de Vries, Henk,Patberg, Marius,Jan-Smith, Eliot,Frehland, Bastian,Schepmann, Dirk,Heitman, Laura H.,Wünsch, Bernhard
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supporting information
p. 409 - 422
(2018/02/14)
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- THIABENDAZOLEMONO (METH) ACRYLATE COMPOUND AND METHOD FOR PRODUCING THE SAME
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PROBLEM TO BE SOLVED: To provide a monofunctional (meth) acrylate compound of a high refractive index which can be used as an optical material (particularly diluent), where the monofunctional (meth) acrylate compound can be produced with high yields by a method suitable for industrial production, and a method for producing the same. SOLUTION: The present invention provides a thiabendazolemono (meth) acrylate compound represented by formula (1) (R1 is H or a methyl group, R2-R5 independently represent H, a halogen atom, a branched/linear C1-8 alkyl group, a branched/linear C1-8 alkoxy group or aryl group). SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
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Paragraph 0050
(2017/05/11)
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- Macroscopic Wires from Fluorophore-Quencher Dyads with Long-Lived Blue Emission
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We report the formation of macroscopic wires up to centimeters in length from a series of structurally flexible, covalently tethered small-molecular fluorophore-quencher dyads (FQDs, average MW = 425 Da), comprised of carbazole, melatonin, and cyanobenzoa
- Wang, Tao,Wu, Ziye,Sun, Wei,Jin, Shengye,Zhang, Xingyuan,Zhou, Chuanyao,Jiang, Jun,Luo, Yi,Zhang, Guoqing
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p. 7183 - 7190
(2017/10/10)
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- Carbazole derivatives as friction light-emitting material in the production of the pressure-sensitive body or pressure sensor in the application of the
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The invention discloses application of a carbazole derivative as a triboluminescence material to manufacturing of a pressure-sensitive luminophor or a pressure sensor. The carbazole derivative has the following structural general formula shown in the description, wherein n is an integer between 1 and 11. The invention also specifically discloses a preparation process of the carbazole derivative. In the preparation process, an anaerobic and waterless system is adopted, and a solvent for use is purified before used, and a reaction is performed under an inert atmosphere, thus obtaining a needle-like crystal substance. Obvious blue light can be seen when the carbazole derivative is scraped by using a metal spoon, and therefore, with the triboluminescence performance, the carbazole derivative as the triboluminescence material has better application prospect in the manufacturing of the pressure-sensitive luminophor or the pressure sensor.
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Paragraph 0010; 0011
(2017/08/24)
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- METHOD FOR PRODUCING N-(2-HYDROXYETHYL) CARBAZOLES
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PROBLEM TO BE SOLVED: To provide a method capable of producing N-(2-hydroxyethyl) carbazoles with high selectivity at a low cost by a process suitable for industrial production. SOLUTION: N-(2-hydroxyethyl) carbazoles can be produced by reacting an N-unsubstituted carbazole and an ethylene carbonate with each other in the presence of a salt containing halogen ions without using a large amount of expensive compound with poor handleability, such as tertiary amines, a diazabicyclo base, and potassium hydride. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0048
(2017/05/02)
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- An efficient ultrasound-assisted synthesis of n-alkyl derivatives of carbazole, indole, and phenothiazine
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Heterocyclic compounds bearing an acidic hydrogen atom attached to nitrogen such as carbazole, indole, and phenothiazine can be efficiently alkylated in DMSO or N,N-DMF under ultrasonic irradiation in the presence of potassium hydroxide as a base. In almost all cases, a dramatic reduction of the reaction time results and a clear yield increase accompanied by an improved quality of the products occurs.
- Zhao, Sanhu,Kang, Jin,Du, Yuting,Kang, Jingyan,Zhao, Xiaoni,Xu, Yinfeng,Chen, Ruixi,Wang, Qianqian,Shi, Xitao
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supporting information
p. 683 - 689
(2014/06/10)
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- Hydroxyalkylation with cyclic sulfates: Synthesis of carbazole derived CB2 ligands with increased polarity
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In order to increase the polarity of the potent CB2 ligand 1a, the homologous hydroxyalkyl carbazoles 2a-c were prepared and pharmacologically evaluated. An important step in the synthesis is the hydroxyalkylation of carbazole with cyclic sulfa
- Lueg, Corinna,Galla, Fabian,Frehland, Bastian,Schepmann, Dirk,Daniliuc, Constantin G.,Deuther-Conrad, Winnie,Brust, Peter,Wuensch, Bernhard
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- Mastering tricyclic ring systems for desirable functional cannabinoid activity
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There is growing interest in using cannabinoid receptor 2 (CB2) agonists for the treatment of neuropathic pain and other indications. In continuation of our ongoing program aiming for the development of new small molecule cannabinoid ligands, we have synthesized a novel series of carbazole and γ-carboline derivatives. The affinities of the newly synthesized compounds were determined by a competitive radioligand displacement assay for human CB2 cannabinoid receptor and rat CB1 cannabinoid receptor. Functional activity and selectivity at human CB1 and CB2 receptors were characterized using receptor internalization and [35S]GTP-γ-S assays. The structure-activity relationship and optimization studies of the carbazole series have led to the discovery of a non-selective CB1 and CB2 agonist, compound 4. Our subsequent research efforts to increase CB2 selectivity of this lead compound have led to the discovery of CB2 selective compound 64, which robustly internalized CB2 receptors. Compound 64 had potent inhibitory effects on pain hypersensitivity in a rat model of neuropathic pain. Other potent and CB2 receptor-selective compounds, including compounds 63 and 68, and a selective CB1 agonist, compound 74 were also discovered. In addition, we identified the CB2 ligand 35 which failed to promote CB2 receptor internalization and inhibited compound CP55,940-induced CB2 internalization despite a high CB2 receptor affinity. The present study provides novel tricyclic series as a starting point for further investigations of CB2 pharmacology and pain treatment.
- Petrov, Ravil R.,Knight, Lindsay,Chen, Shao-Rui,Wager-Miller, Jim,McDaniel, Steven W.,Diaz, Fanny,Barth, Francis,Pan, Hui-Lin,Mackie, Ken,Cavasotto, Claudio N.,Diaz, Philippe
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p. 881 - 907
(2013/11/19)
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- Design and synthesis of carbamate and thiocarbamate derivatives and their inhibitory activities of NO production in LPS activated macrophages
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Series of carbamate and thiocarbamate derivatives were designed and synthesized and their inhibitory activities of NO production in lipopolysaccharide-activated macrophages were evaluated. Several thoicarbamate derivatives revealed promising inhibitory ac
- Jin, Guo Hua,Lee, Hwa Jin,Gim, Hyo Jin,Ryu, Jae-Ha,Jeon, Raok
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supporting information; experimental part
p. 3301 - 3304
(2012/06/18)
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- Synthesis of heterocycle-linked thioureas and their inhibitory activities of NO production in LPS activated macrophages
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A series of thioureas were synthesized as inhibitors of NO production in lipopolysaccharide-activated macrophages. We investigated the effect of lipophilic moiety and N-substituents of the thioureas on the activity. Phenoxazine and carbazole-containing de
- Cheon, Ye-Jin,Gim, Hyo Jin,Jang, Hee Ryun,Ryu, Jae-Ha,Jeon, Raok
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scheme or table
p. 27 - 30
(2010/08/20)
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- Synthesis of phenylisothiourea derivatives as inhibitors of NO production in LPS activated macrophages
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A series of phenylisothioureas were synthesized as inhibitors of NO production in lipopolysaccharide-activated macrophages. We investigated the effect of lipophilic moiety and N- or S-substituents of the phenylisothioureas on the activity. Inhibitory acti
- Jin, Guo Hua,Lee, Da Yeon,Cheon, Ye-Jin,Gim, Hyo Jin,Kim, Do Hee,Kim, Hee-Doo,Ryu, Jae-Ha,Jeon, Raok
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supporting information; experimental part
p. 3088 - 3092
(2010/03/03)
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- Design and synthesis of urea and thiourea derivatives and their inhibitory activities on lipopolysaccharide-induced NO production
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Series of ureas and thioureas were designed and synthesized, and their inhibitory activities of NO production in lipopolysaccharide-activated macrophages were evaluated. We found several essential moieties in the structure of the prepared compounds for th
- Kim, Yoon Jung,Ryu, Jae-Ha,Cheon, Ye Jin,Lim, Hyo Jin,Jeon, Raok
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p. 3317 - 3321
(2008/02/09)
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- Microstructure characterization of poly(2-N-carbazolylethyl acrylate) by two-dimensional NMR spectroscopy
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Poly(2-N-carbazolylethyl acrylate) has been synthesized by solution polymerization of 2-N-carbazolyethyl acrylate with 2,2′- azobisisobutyronitrile as free radical initiator. Distortionless Enhancement by Polarization Transfer has been used to distinguish between the overlapping main-chain methine and side-chain methylene resonances in 13C( 1H) NMR spectrum. Configurational assignments of carbon and proton resonances of main-chain methylene group have been done using two-dimensional Heteronuclear Single Quantum Correlation spectroscopy and two-dimensional Total Correlation Spectroscopy. Two and three bond order carbon/proton couplings have been investigated using Heteronuclear Multiple Bond Correlation studies.
- Brar,Markanday,Gandhi
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- Colorant for ocular lenses and colored ocular lens using the colorant
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A colorant for ocular lenses represented by the following formula (1): wherein A and B are each selected from the group consisting of halogens, a cyano group, a nitro group, alkyl groups, alkylsulfonyl groups and alkoxy groups; R represents a linear or br
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- Synthesis and solid state structures of N,N′-linked carbazoles and indoles
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The synthesis and solid state conformations of a number of N,N′-linked carbazoles and indoles has been investigated. Using xylyl-based linkers, the o, m and p-linked carbazoles and indoles 4-6, 8-10 and 12, 13 were prepared. Likewise, unsymmetrical deriva
- Bloxham, Jason,Moody, Christopher J,Slawin, Alexandra M.Z
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p. 3709 - 3720
(2007/10/03)
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- Chromophoric carbazole methacrylates as intermediates for photorefractive applications
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Methacrylate monomers containing a carbazole fragment and a chromophoric azophenyl sulfonyl group were synthesized, being characterized as definite chemical species and as potential intermediates for photorefractive applications. Quantum chemical calculat
- Diduch,Kucharski
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p. 1495 - 1503
(2007/10/03)
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- Efficient fully functionalized photorefractive polymethacrylates with infrared sensitivity and different spacer lengths
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A series of photorefractive polymethacrylates, containing a Disperse Red type chromophore and carbazole as charge transport agent with various spacer lengths, was synthesized and characterized. The photorefractive effect of these materials was studied by
- Engels, Christiaan,Van Steenwinckel, David,Hendrickx, Eric,Schaerlaekens, Mark,Persoons, Andre,Samyn, Celest
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p. 951 - 957
(2007/10/03)
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- 3-piperidyl-4-oxoquinazoline derivatives and pharmaceutical compositions comprising the same
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3-piperidyl-4-oxoquinazoline derivatives are provided, which is represented by the formula (I): wherein R represents an amino group or a cyclic amino group such as dibenzoazepine, each of which is substituted with a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or the like, n is an integer of 1 to 3, R3and R4independently represents a hydrogen atom, a lower alkyl group, or the like, or a pharmaceutically acceptable salt thereof. Compounds (I) of the present invention have excellent MTP-inhibitory activity. Thus, these compounds not only inhibit formation of LDL that is a cause of arteriosclerotic diseases but also regulate TG, cholesterol, and lipoproteins such as LDL in the blood and regulate cellular lipids through regulation of MTP activity. They can also be used as a new type of preventive or therapeutic agents for hyperlipemia or arteriosclerotic diseases. Furthermore, they can be used as therapeutic or preventive agents for pancreatitis, obesity, hypercholesterolemia, and hypertriglyceridemia.
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- Anionic living polymerization of monomers with photo-electronic properties for control of polymeric nano architectures
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Block copolymers, 9-ethylcarbazolyl methacrylate (CzMA) with 3-nitro-9-ethylcarbazolyl methacrylate (NCzMA), and styrene with optically functionalized isocyanates containing disperse red 1 (DR1NCO) and (s)-(-)-2-methylbutanol (MBI), were prepared by anionic polymerization for photo-electronic materials. The living condition of CzMA was found at -78°C for 3 h with diethyl zinc and block copolymers of CzMA with NCzMA were synthesized successfully. The polymers show potential to be used as energy transfer materials in UV and PL spectra. Block copolymers of styrene with optically functionalized isocyanates were also synthesized with high yield and the polymers showed the large optical activity at 476 nm.
- Shin, Yeong-Deuk,Cho, Young-Sun,Kim, Jang-Joo,Lee, Jae-Suk,Han, Song-Hee,Wu, Jeong Weon
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- Convergent functional groups. 13. High-affinity complexation of adenosine derivatives within induced binding pockets
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Receptors based upon 3,6-diaminocarbazole have been synthesized that bind to adenosine derivatives with an interaction energy of approximately 8 kcal/mol in CDCl3 and over 3 kcal/mol in CD3OD. The purine nucleus is bound within a cavity by simultaneous Watson-Crick and Hoogsteen base-pairing, hydrogen bonding to N3, and stacking on both of its aromatic faces. Hydrogen bond interactions can be estimated at approximately 0.5-0.75 kcal/mol in methanol. The structure of the complex in solution has been deduced through binding assays of incremental derivatives, one- and two-dimensional NMR studies, and molecular modeling.
- Conn, M. Morgan,Deslongchamps, Ghislain,De Mendoza, Javier,Rebek Jr., Julius
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p. 3548 - 3557
(2007/10/02)
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- A NOVEL SYNTHESIS OF POLYACRYLATES AND POLYMETHACRYLATES WITH PENDANT CARBAZOLE GROUPS
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A series of novel polyacrylates and polymethacrylates with pendant carbazole groups has been prepared.In these polymers the carbazole groups are separated from the polymer backbone by alkyl spacers of variable length.The title compounds have been prepared by two different methods: free radical polymerization of the corresponding acrylates and methacrylates and a novel polymeranalogous reaction of ω-hydroxyalkylcarbazoles with poly(meth)acryloylchloride.
- Strohriegl, Peter
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p. 261 - 267
(2007/10/02)
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- Efficient Singlet Energy Migration in Amorphous Copolymer Film Having No Excimer Forming Site: Poly
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Singlet energy migration in the solid state for the homopolymer of 2-(9-carbazolyl)ethyl methacrylate and the copolymers with methyl methacrylate was investigated using perylene as an acceptor molecule.In this system, the carbazole (Cz) chromophore is dispersed uniformly even in the homopolymer and a deep trap is not formed.The fluorescence spectra and their decays were measured for these samples and the energy migration was analyzed on the basis of three models, i.e., random hopping model, Smoluchowski diffusion model, and Yokota-Tanimoto (Y-T) Pade model.Among these models, the Y-T Pade model gave the most reliable diffusion coefficient.The diffusion coefficient was obtained in a wide range of carbazole concentrations from 0.14 to 4.4 mol/l and we obtained the following conclusions. 1.The energy diffusion coefficient D is proportional to 4/3 as predicted fron the Foerster mechanism even for the samples of Cz concentration higher than 1 mol/l. 2.At a low temperature, the energy migration rate becomes slow owing to shallow traps.The activation energy in a low temperature region is about 4 kJ/mol. 3.Fast energy migration (D = 2.0*1E-4 cm2/s) was found for the polymers whose concentration of Cz-chromophore is high, but do not form excimer. - Key words: Energy Transfer / Fluorescence / Polymers
- Ohmori, Satoru,Ito, Shinzaburo,Yamamoto, Masahide
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p. 815 - 824
(2007/10/02)
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- Electrically conductive liquid crystalline substance and polymer
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An electrically conductive liquid crystalline substance represented by the general formula L-S1 -CT or L-CT, wherein L is a residue of a liquid crystalline substance, S1 is an atom or atomic grouping which becomes a spacer and CT is a charge-transfer complex, is disclosed. An electrically conductive liquid crystalline polymer having an electrically conductive liquid crystalline substance portion in its side chain is also provided. These electrically conductive liquid crystalline materials are useful in the conventional applications of liquid crystals and in other applications which utilize their electrical conductivity.
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- A Convenient and One-pot Synthesis of 9-Substituted Carbazoles from Primary Amine Hydrochlorides and 2,5-Dimethoxytetrahydrofuran
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Carbazoles are the very important compounds in material science, nevertheless conventional syntheses required severe and very complicated reaction conditions.In the process of preparation of pyrrole derivatives, we found that a primary amine hydrochloride 1 and 2,5-dimethoxytetrahydrofuran 2 were refluxed in benzene-water (100:4 (v/v)) mixture to be obtained 9-substituted carbazole 5 in a high yield.This method is the one-pot synthesis of 9-substituted carbazoles 5 under mild and convenient conditions.
- Kashima, Choji,Hibi, Shigeki,Maruyama, Tatsuya,Harada, Kazuo,Omote, Yoshimori
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p. 913 - 916
(2007/10/02)
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- THE CONVENIENT AND ONE-POT SYNTHESIS OF N-SUBSTITUTED CARBAZOLES
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In spite of the very important compounds in the material sciences, conventional syntheses of carbazoles required severe and complicated reaction conditions.We can now report the convenient and one-pot synthesis of N-substituted carbazoles under mild conditions.
- Kashima, Choji,Hibi, Shigeki,Maruyama, Tatsuya,Omote, Yoshimori
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p. 2131 - 2134
(2007/10/02)
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