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Sample records for pyrans

  1. Synthesis of Polyfunctionalized 4H-Pyrans

    Directory of Open Access Journals (Sweden)

    Manisha Bihani

    2013-01-01

    Full Text Available Amberlyst A21 catalyzed one-pot three-component coupling of aldehyde and malononitrile with active methylene compounds such as acetylacetone and ethyl acetoacetate for the synthesis of pharmaceutically important polyfunctionalized 4H-pyrans has been reported. Simple experimental procedure, no chromatographic purification, no hazardous organic solvents, easy recovery and reusability of the catalyst, and room temperature reaction conditions are some of the highlights of this protocol for the synthesis of pharmaceutically relevant focused libraries.

  2. Spectral, luminescent and lasing properties of pyran derivatives

    International Nuclear Information System (INIS)

    Kopylova, T N; Svetlichnyi, Valerii A; Samsonova, L G; Svetlichnaya, N N; Reznichenko, A V; Ponomareva, O V; Komlev, I V

    2003-01-01

    The spectral, luminescent and lasing properties of eight organic molecules, substituted pyrans (DCM), are studied upon pumping by an exciplex XeCl laser at 308 nm and by the second harmonic from a Nd:YAG laser at 532 nm. These molecules exhibit lasing in the red spectral region between 600 and 780 nm with the efficiency of 45%. Lasing was also obtained in bis-substituted pyrans having the quantum yield of fluorescence equal to 0.01. The possibility of preparation of solid active media for tunable lasers based on polymer matrices doped with substituted pyrans is discussed. (active media. lasers)

  3. Pyrones to pyrans: enantioselective radical additions to acyloxy pyrones.

    Science.gov (United States)

    Sibi, Mukund P; Zimmerman, Jake

    2006-10-18

    This paper describes a highly site-, diastereo-, and enantioselective intermolecular radical addition/hydrogen atom transfer to hydroxypyrone pyromeconic and kojic acids. The methodology can be extended to the formation of chiral quaternary centers. The products obtained are densely functionalized pyran moieties. The products contain structural features amenable for the introduction of additional substituents.

  4. Crystal structure of di-bromo-meth-oxy-seselin (DBMS), a photobiologically active pyran-ocoumarin.

    Science.gov (United States)

    Bauri, A K; Foro, Sabine; Rahman, A F M M

    2017-05-01

    The title compound, C 15 H 14 Br 2 O 4 [systematic name: rac -(9 S ,10 R )-3,9-dibromo-10-methoxy-8,8-dimethyl-9,10-dihydropyrano[2,3- h ]chromen-2(8 H )-one], is a pyran-ocoumarin derivative formed by the bromination of seselin, which is a naturally occurring angular pyran-ocoumarin isolated from the Indian herb Trachyspermum stictocarpum . In the mol-ecule, the benzo-pyran ring system is essentially planar, with a maximum deviation of 0.044 (2) Å for the O atom. The di-hydro-pyran ring is in a half-chair conformation and the four essentially planar atoms of this ring form a dihedral angle of 4.6 (2)° with the benzo-pyran ring system. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming chains propagating along [010]. In addition, π-π stacking inter-actions, with centroid-centroid distances of 3.902 (2) and 3.908 (2) Å, link the hydrogen-bonded chains into layers parallel to (001).

  5. Synthesis, characterization, photophysics and electroluminescence based on a series of pyran-containing emitters

    Energy Technology Data Exchange (ETDEWEB)

    Yang Lifen [State Key Laboratory of Rare Earth Materials Chemistry and Applications, Peking University, Beijing 100871 (China); Guan Min [State Key Laboratory of Rare Earth Materials Chemistry and Applications, Peking University, Beijing 100871 (China); Bian Zuqiang [State Key Laboratory of Rare Earth Materials Chemistry and Applications, Peking University, Beijing 100871 (China)]. E-mail: bianzq@pku.edu.cn; Xie Junqi [State Key Laboratory of Rare Earth Materials Chemistry and Applications, Peking University, Beijing 100871 (China); Chen Tianpeng [State Key Laboratory of Rare Earth Materials Chemistry and Applications, Peking University, Beijing 100871 (China); Huang Chunhui [State Key Laboratory of Rare Earth Materials Chemistry and Applications, Peking University, Beijing 100871 (China)]. E-mail: chhuang@pku.edu.cn

    2006-04-03

    Four unsymmetric as well as symmetric carbazole or oxadiazole modified pyran-containing compounds have been synthesized and characterized. These compounds are 4-(dicyanomethylene)-2-methyl-6-(4-(carbazolo-9-yl)phenyl)-4H-pyran (10), 4-(dicyanomethylene)-2,6-bis(4-(carbazolo-9-yl)phenyl)-4H-pyran (11), 4-(dicyanomethylene)-2-methyl-6-(4-tert-phenyl)-1,3,4-oxdiazole-4-phenyl)-4 H-pyran (12), and 4-(dicyanomethylene)-2,6-bis(4-tert-phenyl)-1,3, 4-oxdiazole-4-phenyl-4H-pyran (13). Photoluminescent measurements indicated that their maximal emissions can be tuned from 543 to 590 nm in acetone solution. Electroluminescent studies based on these compounds as dopants resulted in greenish yellow light emission. It was found that the device based on the bis-condensed symmetric compound (11) with the configuration of indium tin oxide / Copper (II) phthalocyanine (5 nm) / N,N'-bis-(1-naphthl)-diphenyl-1,1'-biphenyl-4,4'-diamine (40 nm) / compound (11) : tris-(8-quinolinolato)aluminium (Alq{sub 3}) (1%) (30 nm) / 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (5 nm) / Alq{sub 3} (40 nm) / Mg : Ag (9 : 1) (200 nm) / Ag (80 nm) has achieved the highest luminance (6869 cd/m{sup 2}) and efficiency (1.32 lm/W and 2.52 cd/A) among the four emitters.

  6. Synthesis of Some O-Substituted Derivatives of Natural 6-hydroxymethyl-4-methoxy-2H-pyran-2-one (opuntiol)

    International Nuclear Information System (INIS)

    Shahzadi, T.; Akhtar, M.; Rehman, A.; Riaz, T.; Ashraf, M.

    2013-01-01

    This manuscript reports the synthesis of a series of new O-substituted derivatives of opuntiol (1) which is a naturally occurring compound isolated from a plant Opuntia dillenii Haw belonging to family Cactaceae. These derivatives 3a-t, were characterized by FAB-MS, IR, and 1H-NMR and then screened against acetylcholinesterase, butyrylcholinesterase, lipoxygenase and H-chymotrypsin enzymes. The screening results revealed that 6-(acetyloxy) methyl- 4-methoxy-2H-pyran-2-one (3b) and N-(2,5-dimethylphenyl)-2-((4-methoxy-6-oxo-2H-pyran-2-yl) methoxy)acetamide (3p) were found to be the inhibitor of butyrylcholinesterase while 6-(acetyloxy) methyl- 4-methoxy-2H-pyran-2-one (3b), 6-(ethoxymethyl)-4-methoxy-2H-pyran-2-one (3c), 4-methoxy-6-((phenylmethoxy)methyl)-2H-pyran-2-one (3g), 6-((2-bromoethyloxy)methyl)-4-methoxy-2H-pyran-2-one (3j), N-(5-chloro-2-ethoxyphenyl)-2-((4-methoxy-6-oxo-2H-pyran-2-yl)methoxy) acetamide (3r), N-(3,4-dimethylphenyl)-2-((4-methoxy-6-oxo-2H-pyran-2-yl)methoxy)acetamide (3s) N-(3,5-dimethylphenyl)-2-((4-methoxy-6-oxo-2H-pyran-2-yl)methoxy)acetamide (3t) were found to be active against H-chymotrypsin and among these 3s was the good inhibitor of this enzyme having IC50 value of 142.71 +- 0.22 micro moles/L. (author)

  7. Green synthesis of tetrahydrobenzo[b]Pyrans by microwave assisted multi-component one-pot reactions in PEG-400.

    Science.gov (United States)

    Feng, Chun; Wang, Qiuyan; Lu, Cuifen; Yang, Guichun; Chen, Zuxing

    2012-01-01

    Polyethylene glycol is found to be a nontoxic and recyclable reaction medium for the microwave-assisted, multi-component one-pot reactions of aromatic aldehydes with ethyl-2-cyanoacetate and 1,3-cyclohexanedione or 5,5- dimethyl-1,3-cyclohexanedione in the presence of piperidine. This environmentally friendly microwave protocol offers ease of operation and enables recyclability of reaction medium and synthesis of a variety of substituted tetrahydrobenzo[b]pyran derivatives. It is an efficient, promising, and green synthetic strategy to construct tetrahydrobenzo[b]pyran skeleton.

  8. (E-4-Hydroxy-6-methyl-3-[1-(2-phenylhydrazinylideneethyl]-2H-pyran-2-one

    Directory of Open Access Journals (Sweden)

    Samra Rahmouni

    2016-05-01

    Full Text Available The title compound, C14H14N2O3, crystallized with three crystallographically independent molecules (A, B and C in the asymmetric unit. The three molecules each have an E conformation about the C=N bond but differ in the orientation of the phenyl and pyran rings. The dihedral angles between the phenyl and pyran ring planes are 14.30 (1, 28.38 (1 and 25.58 (1° in molecules A, B and C, respectively. There is an intramolecular O—H...N hydrogen bond in each molecule with an S(6 ring motif. In the crystal, molecules are linked by N—H...O and C—H...O hydrogen bonds, forming layers parallel to (001, enclosing R22(8 and R33(21 ring motifs. The layers are linked via C—H...π interactions, forming bilayers, which are joined by a further C—H...π interaction, forming a three-dimensional structure.

  9. Temperature dependence of (+)-catechin pyran ring proton coupling constants as measured by NMR and modeled using GMMX search methodology

    Science.gov (United States)

    Fred L. Tobiason; Stephen S. Kelley; M. Mark Midland; Richard W. Hemingway

    1997-01-01

    The pyran ring proton coupling constants for (+)-catechin have been experimentally determined in deuterated methanol over a temperature range of 213 K to 313 K. The experimental coupling constants were simulated to 0.04 Hz on the average at a 90 percent confidence limit using a LAOCOON method. The temperature dependence of the coupling constants was reproduced from the...

  10. pyran Derivatives

    African Journals Online (AJOL)

    NICO

    electrochemical and optical properties, as well as their good stability.1–4 Polyaniline is ... Realizing the importance of these compounds, various methods .... images were obtained on JEOL; JSM-6330 LA operated at 20.0 kV and 1.0000 nA.

  11. Ultrasound mediated, iodine catalyzed green synthesis of novel 2-amino-3-cyano-4H-pyran derivatives.

    Science.gov (United States)

    Tabassum, Sumaiya; Govindaraju, Santhosh; Khan, Riyaz-ur-Rahaman; Pasha, Mohamed Afzal

    2015-05-01

    An efficient synthesis of a novel series of twelve substituted 2-amino-3-cyano-4H-pyran derivatives was achieved by a one-pot three-component cyclocondensation reaction of heteroaryl aldehydes, malononitrile and active methylene compounds catalyzed by iodine in aqueous medium under ultrasound irradiation. In comparison with conventional methods, our protocol is convenient and offers several advantages, such as shorter reaction time, higher yields, milder conditions and environmental friendliness. We have herein successfully demonstrated the synergistic outcome of multi-component reaction (MCR) and sonication to offer a facile route for the design of these derivatives. Copyright © 2014 Elsevier B.V. All rights reserved.

  12. An Efficient and Green Synthesis of 5-Oxo-5,6,7,8-tetrahydro 4H-benzo-[b]-pyran Derivatives Promoted by InCl3·4H2O Under Microwave Irradiation

    Institute of Scientific and Technical Information of China (English)

    Xue Yuan HU; Xue Sen FAN; Xin Ying ZHANG; Gui Rong QU; Yan Zhen LI

    2005-01-01

    A rapid and facile preparation of benzo-[b]-pyran derivatives through condensation of chalcone and 5, 5-dimethyl-1,3-cyclohexandione under microwave irradiation in the presence of simplicity and environmental benignancy, this method may provide a useful alternative for the preparation of benzo-[b]-pyran derivatives.

  13. Theoretical study on the Diels-Alder reaction of bromo-substituted 2H-pyrane-2-ones and some substituent vinyls

    Directory of Open Access Journals (Sweden)

    Haghdadi Mina

    2015-01-01

    Full Text Available A DFT study of the reactivity, regio- and stereoselectivity of Diels-Alder reaction between 3-bromo, 5-bromo, and 3,5-dibromo-2(H-pyran-2-ones and some weakly activated and unactivated alkenes has been carried out using density functional theory (DFT. Four possible reaction channels, which are related to the formation of meta- and para- and endo- and exo-cycloadducts have been explored and characterized. The energy and natural bond orbital analysis shows that the meta-regioselectivity on the exo pathway is preferred and follows an asynchronous concerted mechanism with a polar nature in all Diels-Alder cycloadditions. Moreover, the activation free energies of Diels-Alder cycloadditions of 3,5-dibromo-2(H-pyran-2one are lower than 3- bromo-2(H-pyran-2one and 5-bromo-2(H-pyran-2one, which are in line with experimental observation. DFT-based reactivity indices clearly predict the regiochemistry of the isolated cycloadducts.

  14. Genotoxicity evaluation of two kinds of smoke-water and 3,7-dimethyl-2H-furo[2,3-c]pyran-2-one

    Czech Academy of Sciences Publication Activity Database

    Trinh, C.; Gevaert, L.; Kohout, Ladislav; van Staden, J.; Verschaeve, L.

    2010-01-01

    Roč. 30, č. 6 (2010), s. 596-602 ISSN 0260-437X Institutional research plan: CEZ:AV0Z40550506 Keywords : butenolide * smoke -water * 3,7-dimethyl-2H-furo[2,3-c]pyran-2-one * assay * seed germination Subject RIV: CC - Organic Chemistry Impact factor: 2.322, year: 2010

  15. One-pot synthesis of 2H-pyrans by indium(III) chloride-catalyzed reactions. efficient synthesis of pyranocoumarins, pyranophenalenones, and pyranoquinolinones

    International Nuclear Information System (INIS)

    Lee, Yong Rok; Kim, Do Hoon; Shim, Jae Jin; Kim, Seog K.; Park, Jung Hag; Cha, Jin Soon; Lee, Chong Soon

    2002-01-01

    An efficient synthesis of 2H-pyrans is achieved by indium (III) chloride-catalyzed reactions of 1,3-dicarbonyl compounds with a variety of α.β-unsaturated aldehydes in moderates yields. This method has been applied to the synthesis of pyranocoumarins, pyranophenaleneones, and pyranoquinolinone alkaloids

  16. One-pot synthesis of 2H-pyrans by indium(III) chloride-catalyzed reactions. efficient synthesis of pyranocoumarins, pyranophenalenones, and pyranoquinolinones

    Energy Technology Data Exchange (ETDEWEB)

    Lee, Yong Rok; Kim, Do Hoon; Shim, Jae Jin; Kim, Seog K.; Park, Jung Hag; Cha, Jin Soon; Lee, Chong Soon [Yeungnam Univ., Kyongsan (Korea, Republic of)

    2002-08-01

    An efficient synthesis of 2H-pyrans is achieved by indium (III) chloride-catalyzed reactions of 1,3-dicarbonyl compounds with a variety of {alpha}.{beta}-unsaturated aldehydes in moderates yields. This method has been applied to the synthesis of pyranocoumarins, pyranophenaleneones, and pyranoquinolinone alkaloids.

  17. Fluorescence and amplified spontaneous emission of glass forming compounds containing styryl-4H-pyran-4-ylidene fragment

    Energy Technology Data Exchange (ETDEWEB)

    Vembris, Aivars, E-mail: aivars.vembris@cfi.lu.lv [Institute of Solid State Physics, University of Latvia, 8 Kengaraga Street, Riga LV-1063 (Latvia); Muzikante, Inta [Institute of Solid State Physics, University of Latvia, 8 Kengaraga Street, Riga LV-1063 (Latvia); Karpicz, Renata; Sliauzys, Gytis [Institute of Physics, Center for Physical Sciences and Technology, A. Gostauto 11, LT-01108 Vilnius (Lithuania); Miasojedovas, Arunas; Jursenas, Saulius [Institute of Applied Research, Vilnius University, Sauletekio 9-III, LT-10222 Vilnius (Lithuania); Gulbinas, Vidmantas [Institute of Physics, Center for Physical Sciences and Technology, A. Gostauto 11, LT-01108 Vilnius (Lithuania)

    2012-09-15

    Potential of glassy films of newly synthesised low molecular weight organic molecules for light amplification and lasing applications has been investigated by analysing fluorescence, transient differential absorption and amplified spontaneous emission properties. These non-symmetric and symmetric molecules contain styryl-4H-pyran-4-ylidene fragment with three different electron acceptor groups: dicyanomethylene, barbituric acid, indene-1,3-dione. Fluorescence quantum yields of the investigated compounds in solutions are between 0.32 and 0.54, while they drop down by an order of magnitude in thin solid films. Incorporation of bulky side groups reduced excitonic interactions enabling manifestation of amplified spontaneous emission in the neat films of the investigated derivatives. - Highlights: Black-Right-Pointing-Pointer Bulky substituents attached to DCM dye enable formation of neat glassy films. Black-Right-Pointing-Pointer Investigated dyes show amplified spontaneous emission in neat films. Black-Right-Pointing-Pointer Two electron donor groups negatively influence light amplification.

  18. Synthesis of 6-Substituted 2-Pyrones Starting from Renewable Resources: Total Synthesis of Sibirinone, (E)-6-(Pent-1-en-1-yl)-2H-pyran-2-one, and (E)-6-(Hept-1-en-1-yl)-2H-pyran-2-one.

    Science.gov (United States)

    Dobler, Daniel; Reiser, Oliver

    2016-11-04

    An atom-economic reaction sequence to 6-substituted 2-pyrones was developed starting from furfuryl alcohol, a renewable resource made from bran or bagasse, and aldehydes, utilizing a thermal rearrangement of cyclopentadienone epoxides as key step. Derivatives bearing a hydroxyalkyl side chain could be enzymatically resolved, providing access to enantiomerically pure 2-pyrones, or converted to alkenyl-substituted 2-pyrones such as naturally occurring sibirinone, (E)-6-(pent-1-en-1-yl)-2H-pyran-2-one, and (E)-6-(hept-1-en-1-yl)-2H-pyran-2-one.

  19. Synthesis and Characterization of a Novel Nanosilica Supported Bipyridinium Chloride Nanocomposite and its Application as a Basic Catalyst in the One-pot Preparation of Tetrahydrobenzo[b]pyran, Dihydropyrano[3,2-c]chromene and Dihydropyrano[4,3-b]pyran Derivatives

    Directory of Open Access Journals (Sweden)

    Ali Reza Kiasat

    2016-07-01

    Full Text Available A novel rice-husk-silica supported n-propyl bipyridinium chloride (RHPrBPCl has been prepared. Due to the basicity of RHPrBPCl, it was decided to evaluate its catalytic activity in the one-pot preparation of tetrahydrobenzo[b]pyran, dihydropyrano[3,2-c]chromene and dihydropyrano[4,3-b]pyran derivatives. The catalyst was characterized by FT-IR, SEM and TGA analyses. This methodology offers several advantages including easy work-up procedure, high yields of the products, short reaction times, recyclable catalyst and green reaction medium.

  20. Synthesis and biological evaluation of certain 2-H-Pyran-2-Ones and some derived 1-H-Pyridin-2-One analogs as antimicrobial agents

    International Nuclear Information System (INIS)

    Faidallah, Hassan M.; Al-Saadi, Mohammad S.; Rostom, Sherif A. F.

    2008-01-01

    Pyran-2-one and pyridine-2-one analogs are known to be biological versatile compounds possessing variety of pharmacological activities. Some 4-(4-nitrophenyl)-5, 6-diphenyl-pyran-2-ones and their 1H-pyridin-2-oneanalogs were synthesized and evaluated for their in vitro intermediates and target compounds were discussed. The results evaluated that some compounds exhibited promising antibacterial and antifungal activities. Compound 8; 1-hydroxy-4-(4-nitrophenyl)-5, 6-diphenyl-1H-pyridin-2-one; showed the most potent broad spectrum antimicrobial activity. 1-Methyl-4-(4-nitrophenyl)-5, 6-diphenyl-1H-pyridin-2-thione 12; was able to exert weak growth inhibitory effect against the Mycobacterium tuberculosis. (author)

  1. Computational assessment of the electronic structures of cyclohexa-1,2,4-triene, 1-oxacyclohexa-2,3,5-triene (3delta(2)-pyran), their benzo derivatives, and cyclohexa-1,2-diene. An experimental approach to 3delta(2)-pyran.

    Science.gov (United States)

    Engels, Bernd; Schöneboom, Jan C; Münster, Arno F; Groetsch, Stefan; Christl, Manfred

    2002-01-16

    The six-membered cyclic allenes given in the title have been studied theoretically by means of an MR-CI approach. For all compounds, the allene structures were found to be the ground states in the gas phase. In the cases of cyclohexa-1,2-diene (1), the isobenzene 2, and the isonaphthalene 7, the most stable structures having a planar allene moiety are the diradicals 1b, 2b, and 7b, representing the transition states for the racemization of 1a, 2a, and 7a and being less stable than the latter by 14.1, 8.9, and 11.2 kcal/mol, respectively. At variance with this order, the 3delta(2)-pyran 4 and the chromene 5 have the zwitterions 4c and 5c as the most stable planar structures, which lie only 1.0 and 5.4 kcal/mol above 4a and 5a, respectively. According to the simulation of the solvent effect, 4c even becomes the ground state of 4 in THF solution. The frontier orbitals of the respective states of 2 and 4 suggest different rates and sites for the reaction with nucleophiles. For the first time, the pyran 4 has been generated and trapped. As a precursor for 4, 3-bromo-4H-pyran (9) was chosen, the synthesis of which was achieved on two routes from 4H-pyran. The treatment of 9 with potassium tert-butoxide (KOt-Bu)/18-crown-6 gave 4-tert-butoxy-4H-pyran as the only discernible product, whether styrene or furan was present, indicating the interception of 4 by KOt-Bu. Finally, the disagreement between the experiment and the theory concerning the heat of formation and the electronic nature of the isobenzene 2 is resolved by demonstrating that the experimental data can provide only an upper limit of the DeltaH(f) degrees value.

  2. Ethyl (E)-2-(2,7-dimethyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-4-ylidene)acetate

    OpenAIRE

    Oulemda Bassou; Hakima Chicha; Latifa Bouissane; El Mostapha Rakib; Mohamed Saadi; Lahcen El Ammari

    2017-01-01

    In the title compound, C14H14O5, the two heterocyclic rings are coplanar (r.m.s. deviation = 0.008 Å), with the largest deviation from the mean plane being 0.012 (1) Å. The mean plane through the acetate group is inclined slightly with respect to the oxopyrano[4,3-b]pyran-4-yl system, as indicated by the dihedral angle of 1.70 (7)° between them. Two intramolecular hydrogen bonds, completing S(6) ring motifs, are observed in the molecule. In the crystal, molecules are linked by weak C—H...O hy...

  3. Synthesis, spectral, thermal and biological studies of transition metal complexes of 4-hydroxy-3-[3-(4-hydroxyphenyl-acryloyl]-6-methyl-2H-pyran-2-one

    Directory of Open Access Journals (Sweden)

    BALASAHEB R. ARBAD

    2011-09-01

    Full Text Available The solid complexes of Mn(II, Fe(III, Co(II, Ni(II, and Cu(II with 4-hydroxy-3-[(2E-3-(4-hydroxyphenylprop-2-enoyl]-6-methyl-2H-pyran-2-one, derived from 3-acetyl-6-methyl-2H-pyran-2,4(3H-dione (dehydroacetic acid and 4-hydroxybenzaldehyde, were synthesized and characterized by elemental analysis, conductometry, thermal analysis, magnetic measurements, IR, 1H-NMR and UV–Vis spectroscopy and a biological study. From the analytical and spectral data, the stoichiometry of the complexes was found to be 1:2 (metal:ligand. The physico–chemical data suggest a distorted octahedral geometry for the Cu(II complexes and an octahedral geometry for all the other complexes. The thermal decomposition of all the complexes was studied by the TG–DTA method. The synthesized ligand and its metal complexes were screened for their in vitro antibacterial activity against Gram-negative (Escherichia coli and Gram-positive (Staphylococcus aureus bacterial strains and for in vitro antifungal activity against Aspergillus flavus, Curvularia lunata and Penicillium notatum. The results of these studies showed the metal complexes to be more antibacterial/antifungal against one or more species as compared with the non-complexed ligand.

  4. Thieno[3,2-c]pyran-4-one based novel small molecules: their synthesis, crystal structure analysis and in vitro evaluation as potential anticancer agents.

    Science.gov (United States)

    Nakhi, Ali; Adepu, Raju; Rambabu, D; Kishore, Ravada; Vanaja, G R; Kalle, Arunasree M; Pal, Manojit

    2012-07-01

    Novel thieno[3,2-c]pyran-4-one based small molecules were designed as potential anticancer agents. Expeditious synthesis of these compounds was carried out via a multi-step sequence consisting of few steps such as Gewald reaction, Sandmeyer type iodination, Sonogashira type coupling followed by iodocyclization and then Pd-mediated various C-C bond forming reactions. The overall strategy involved the construction of thiophene ring followed by the fused pyranone moiety and then functionalization at C-7 position of the resultant thieno[3,2-c]pyran-4-one framework. Some of the compounds synthesized showed selective growth inhibition of cancer cells in vitro among which two compounds for example, 5d and 6c showed IC(50) values in the range of 2.0-2.5 μM. The crystal structure analysis of an active compound along with hydrogen bonding patterns and molecular arrangement present within the molecule is described. Copyright © 2012 Elsevier Ltd. All rights reserved.

  5. Ethyl (E-2-(2,7-dimethyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-4-ylideneacetate

    Directory of Open Access Journals (Sweden)

    Oulemda Bassou

    2017-02-01

    Full Text Available In the title compound, C14H14O5, the two heterocyclic rings are coplanar (r.m.s. deviation = 0.008 Å, with the largest deviation from the mean plane being 0.012 (1 Å. The mean plane through the acetate group is inclined slightly with respect to the oxopyrano[4,3-b]pyran-4-yl system, as indicated by the dihedral angle of 1.70 (7° between them. Two intramolecular hydrogen bonds, completing S(6 ring motifs, are observed in the molecule. In the crystal, molecules are linked by weak C—H...O hydrogen bonds involving the same acceptor atom, forming chains propagating along the c-axis direction and enclosing R21(6 ring motifs. The chains are linked via offset π–π interactions [intercentroid distance = 3.622 (1 Å], involving inversion-related oxopyrano[4,3-b]pyran-4-yl ring systems, forming slabs parallel to the bc plane.

  6. Synthesis, characterization, and crystal structure of 2-amino-7-methyl-5-oxo-4-phenyl-4,5-dihydropyrano[3,2-c] pyran-3-carbonitrile

    Energy Technology Data Exchange (ETDEWEB)

    Sharma, S. [University of Jammu, X-ray Crystallography Laboratory, Post-Graduate Department of Physics and Electronics (India); Banerjee, B.; Brahmachari, G. [Visva-Bharati (a Central University), Laboratory of Natural Products & Organic Synthesis, Department of Chemistry (India); Kant, Rajni; Gupta, V. K., E-mail: vivek-gupta2k2@hotmail.com [University of Jammu, X-ray Crystallography Laboratory, Post-Graduate Department of Physics and Electronics (India)

    2015-12-15

    2-Amino-7-methyl-5-oxo-4-phenyl-4,5-dihydropyrano[3,2-c] pyran-3-carbonitrile, C{sub 16}H{sub 12}N{sub 2}O{sub 3} is synthesized via one-pot multi-component reaction at room temperature using commercially available urea as inexpensive and environmentally benign organo-catalyst. Its structure is determined by single-crystal X-ray diffraction technique The crystals are monoclinic, a = 10.7357(12), b = 8.7774(8), c = 15.0759(16) Å, β = 103.575(11)°, Z = 4, sp. gr. P2{sub 1}/n, R = 0.0551 for 1696 observed reflections. The crystal structure is stabilized by N–H···N, C–H···O, and C–H···π interactions.

  7. 2-Acetyl-amino-1,3,4,6-tetra-O-(tri-methyl-silyl)-2-de-oxy-α-d-gluco-pyran-ose.

    Science.gov (United States)

    Cheng, Zhao-Dong; Cui, Yan-Li; Mao, Jian-Wei

    2013-06-01

    The title compound, C20H47NO6Si4, was synthesized by per-O-tri-methyl-silylation of N-acetyl-d-glucosa-mine using chloro-tri-methyl-silane in the presence of hexa-methyl-disiloxane. The tri-methyl-silyl group and acetamido group are located on the same side of the pyran ring, showing an α-configuration glycoside. One of the tri-methyl-silyl groups is disordered over two orientations, with site-occupancy factors of 0.625 (9) and 0.375 (9). In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into supra-molecular chains along the a-axis direction.

  8. 1,3,5-Trihydroxy-13,13-dimethyl-2H-pyran [7,6-b] xanthone directly targets heat shock protein 27 in hepatocellular carcinoma.

    Science.gov (United States)

    Fu, Wei-Ming; Wang, Wei-Mao; Wang, Hua; Zhu, Xiao; Liang, Yan; Kung, Hsiang-Fu; Zhang, Jin-Fang

    2014-02-01

    We previously showed that the small molecule 1,3,5-trihydroxy-13,13-dimethyl-2H-pyran [7,6-b] xanthone (TDP) induces apoptosis in hepatocellular carcinoma (HCC) by suppressing Hsp27 expression, although the mechanism is not fully understood. To investigate the functional association between TDP and Hsp27 protein in HCC, recombinant Hsp27 protein was incubated with TDP at room temperature, and assayed by mass spectrum (MS) and natural electrophoresis. TDP effectively stimulated Hsp27 to form aggregates ex vitro, leading to suppression of its chaperone activity. The aggregates were degraded by the ubiquitin-proteasome (UPS) pathway. TDP directly interacted with Asp17 and Phe55 in chain C of Hsp27 on the basis of bioinformatic prediction. In conclusion, Hsp27 is a direct target of TDP in its anti-cancer activity, which provides strong support for a clinical application. © 2013 International Federation for Cell Biology.

  9. Stereoselective synthesis of 5-alkoxycarbonyl-4 alkyl-2-anino-3-cyano-6-methyl-4H-pyranes 3 via asymmetric Michael addition to aceptors-gamma-stereogenics; Sintesis esteroselective de 5-alcoxicarbonil-4-alquil-2-amino-3-ciano-6-metil-4H-piranos via adicion Michael sobre aceptores-gama-esterogenicos

    Energy Technology Data Exchange (ETDEWEB)

    Martinez-Grau, A.; Jimenez, B.; Martin, N.; Seoane, C.; Marco, J.L. [Departamento de Quimica Organica, Facultad de Quimica, Universidad Complutense, Madrid (Spain)

    1994-12-31

    The stereoselective synthesis of 5-alkoxycarbonyl-4-alkyl-2-amino-3-cyano-6-methyl-4H-pyrans 3 via asymmetric Michael addition of malononitrile to gamma-stereogenic alpha-acetylacrylates 2 obtained by Knoevenagel reaction of acetylacetates to quiral alpha-hydroxyaldehydes 1 is described. The resulting 2-amino-4H-pyrans 3 have been obtained in moderate yield and good diastereoselectivity. 15 refs.

  10. Antimicrobial assay and genetic screening of selected freshwater Cyanobacteria and identification of a biomolecule dihydro-2H-pyran-2-one derivative.

    Science.gov (United States)

    Srivastava, A; Singh, V K; Patnaik, S; Tripathi, J; Singh, P; Nath, G; Asthana, R K

    2017-04-01

    Explorations of freshwater Cyanobacteria as antimicrobial (bacteria, fungi and methicillin-resistant Staphylococcus aureus (MRSA) strains) drug resource using bioassay, NRPS (non-ribosomal polypeptide synthetase) and PKS (polyketide synthase) genes, as well as in silico approach. We have bioassayed the extracts of Phormidium CCC727, Geitlerinema CCC728, Arthrospira CCC729, Leptolyngbya CCC732, Phormidium CCC730, Phormidium CCC731 against six pathogenic bacteria comprising Gram (+ve): S. aureus including seven clinical MRSA and Enterococcus faecalis, Gram (-ve): Escherichia coli, Salmonella Typhimurium, Klebsiella pneumoniae and Shigella boydii along with non-pathogenic Enterobacter aerogenes as well as fungal strains (Cryptococcus neoformans and Candida albicans, C. krusei, C. tropicalis and Aspergillus niger) exhibiting antimicrobial potential. The NRPS and PKS genes of the target strains were also amplified and sequenced. The putative protein structures were predicted using bioinformatics approach. PKS gene expression indicated β keto-acyl synthase as one of the important active domains in the biomolecules related to antitumour and antifungal group. The simultaneous identification of the biomolecule (dihydro-2H-pyran-2-one derivative) was also inferred spectroscopically. Freshwater Cyanobacteria are prolific producers of secondary metabolite(s) that may act as the antimicrobial drug resource in addition to their much explored marine counterpart. © 2016 The Society for Applied Microbiology.

  11. 5-Bromo-3-(3-hydroxyprop-1-ynyl-2H-pyran-2-one targets prostate cancer cells by down-regulating inflammation-related genes

    Directory of Open Access Journals (Sweden)

    Zhao-Yang Wang

    2016-06-01

    Full Text Available The present study was performed to examine the effect of 5-bromo-3-(3-hydroxyprop-1-ynyl-2H-pyran-2-one (BHP on the rate of cell proliferation and apoptosis induction in the PC3, human prostate carcinoma cell line. The cell viability was assayed by using sulphorhodamine B staining and apoptosis by annexin V and flow cytometry analyses. The results revealed that BHP treatment in PC3 cells caused a significant reduction in the rate of cell proliferation in dose- and time-dependent manner. Compared to the un-treated cells, the formation of HUVEC tubes was markedly inhibited on treatment with BHP at a concentration of 30 µM. Further investigation revealed the expression of HMGB1, IL-6 and IL-8, pro-inflammatory cytokines was also inhibited on treatment with BHP. Therefore, BHP treatment plays an important role in inducing apoptosis in the prostrate cells and can be of therapeutic value for the prostate cancer treatment.

  12. A Facile Synthesis of New 2-Amino-4H-pyran-3-carbonitriles by a One-Pot Reaction of ,′-Bis(arylidene Cycloalkanones and Malononitrile in the Presence of KCO

    Directory of Open Access Journals (Sweden)

    Zahed Karimi-Jaberi

    2012-01-01

    Full Text Available A rapid and environmentally friendly method is developed for the synthesis of a series of new substituted 2-amino-4H-pyran-3-carbonitriles through a one-pot condensation of malononitrile and ,-bis(arylidene cycloalkanones in ethanol by using K2CO3 as a catalyst. Short experimental reaction times, excellent yields, no need to use cumbersome apparatus for purification of the products, and inexpensiveness and commercially availability of the catalyst are the advantages of this method.

  13. Ultrasound promoted one-pot synthesis of 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile scaffolds in aqueous media: a complementary 'green chemistry' tool to organic synthesis.

    Science.gov (United States)

    Banitaba, Sayed Hossein; Safari, Javad; Khalili, Shiva Dehghan

    2013-01-01

    A green and simple approach to assembling of 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile scaffolds via three-component reaction of kojic acid, malononitrile, and aromatic aldehydes in aqueous media under ultrasound irradiation is described. The combinatorial synthesis was achieved for this methodology with applying ultrasound irradiation while making use of water as green solvent. In comparison to conventional methods, experimental simplicity, good functional group tolerance, excellent yields, short routine, and selectivity without the need for a transition metal or base catalyst are prominent features of this green procedure. Copyright © 2012 Elsevier B.V. All rights reserved.

  14. (2-Methyl-4-oxo-4H-pyran-3-olato-κ2O3,O4bis(triphenylphosphane-κPcopper(I–triphenylphosphane–methanol (1/1/1

    Directory of Open Access Journals (Sweden)

    Fabian M. A. Muller

    2011-05-01

    Full Text Available In the title compound, [Cu(C6H5O3(C18H15P2]·C18H15P·CH3OH, the pyran-4-one ring is appromimately planar (r.m.s deviation = 0.0138 Å, with the CuI atom 0.451 (5 Å out of the plane. The CuI atom has a distorted tetrahedral coordination. The O—Cu—O angle is 80.07 (8° and the P—Cu—P angle is 123.49 (3°. The crystal packing is stablized by intramolecular C—H...O interactions and intermolecular C—H...O and O—H...O interactions.

  15. 2-Acetyl­amino-1,3,4,6-tetra-O-(tri­methyl­silyl)-2-de­oxy-α-d-gluco­pyran­ose

    Science.gov (United States)

    Cheng, Zhao-Dong; Cui, Yan-Li; Mao, Jian-Wei

    2013-01-01

    The title compound, C20H47NO6Si4, was synthesized by per-O-tri­methyl­silylation of N-acetyl-d-glucosa­mine using chloro­tri­methyl­silane in the presence of hexa­methyl­disiloxane. The tri­methyl­silyl group and acetamido group are located on the same side of the pyran ring, showing an α-configuration glycoside. One of the tri­methyl­silyl groups is disordered over two orientations, with site-occupancy factors of 0.625 (9) and 0.375 (9). In the crystal, N—H⋯O hydrogen bonds link the mol­ecules into supra­molecular chains along the a-axis direction. PMID:23795087

  16. Crystal structure of [(2R,3R,4S)-3,4-bis(acet-yloxy)-5-iodo-3,4-di-hydro-2H-pyran-2-yl]methyl acetate.

    Science.gov (United States)

    Zukerman-Schpector, Julio; Caracelli, Ignez; Stefani, Hélio A; Shamim, Anwar; Tiekink, Edward R T

    2015-01-01

    In the title compound, C12H15IO7, the 3,4-di-hydro-2H-pyran ring is in a distorted half-boat conformation with the atom bearing the acet-yloxy group adjacent to the C atom bearing the methyl-acetate group lying 0.633 (6) Å above the plane of the remaining ring atoms (r.m.s. deviation = 0.0907 Å). In the crystal, mol-ecules are linked into a supra-molecular chain along the a axis through two C-H⋯O inter-actions to the same acceptor carbonyl O atom; these chains pack with no specific inter-molecular inter-actions between them.

  17. 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran (DCM)-doping density dependence of luminescence spectra and white emission in polymer light-emitting diodes

    Energy Technology Data Exchange (ETDEWEB)

    Inoue, Akinori; Hosokawa, Takeshi; Haishi, Motoki; Ohtani, Naoki [Department of Electronics, Doshisha University, Tatara-Miyakodani, Kyotanabe-shi, Kyoto (Japan)

    2009-01-15

    We fabricated white polymer light-emitting diodes (PLEDs), in which the active region is doped with a low-weight molecule. The host polymer material is Poly(9,9-didodecyl-fluorenyl-2,7-yleneethylnylene) (PFO), while the guest luminescent low-weight-molecule is 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran (DCM). The photoluminescence (PL) and electroluminescence (EL) spectra strongly depend on DCM-doping-density. However, the most suitable DCM-doping-densities for white emissions in PL and EL are slightly different. This discrepancy is caused by the difference in excitation efficiencies. The photo-excitation system for PL measurement is better than the current injection for generating carriers efficiently. Thus, the realization of the white EL signal requires the larger DCM-doping-density than that of the white PL signal. (copyright 2009 WILEY-VCH Verlag GmbH and Co. KGaA, Weinheim) (orig.)

  18. Synthesis of novel chromeno-annulated cis-fused pyrano[3,4-c]benzopyran and naphtho pyran derivatives via domino aldol-type/hetero Diels-Alder reaction and their cytotoxicity evaluation.

    Science.gov (United States)

    Madda, Jyothi; Venkatesham, Akkaladevi; Naveen Kumar, Bejjanki; Nagaiah, Kommu; Sujitha, Pombala; Ganesh Kumar, C; Rao, Tadikamalla Prabhakar; Jagadeesh Babu, Nanubolu

    2014-09-15

    New chromeno-annulated cis-fused pyrano[3,4-c]benzopyran and naphtho pyran derivatives have been synthesized by domino aldol-type reaction/hetero Diels-Alder reaction generated from o-quinone methide in situ from 7-O-prenyl derivatives of 8-formyl-2,3-disubstituted chromenones with resorcinols/naphthols in the presence of 20 mol% ethylenediamine diacetate (EDDA), triethylamine (2 mL) as co-catalyst in CH3CN under reflux conditions in good yields. The structures were established based on spectroscopic data, and further confirmed by X-ray diffraction analysis. The results showed that compounds 4h and 4j exhibited very potent cytotoxicity against human cervical cancer cell line (HeLa). Compound 4h displayed good inhibitory activity against both breast cancer cell lines, MDA-MB-231 and MCF-7. Further, the compound 4i exhibited good cytotoxicity against only MDA-MB-231, and compound 4j showed promising activity against human lung cancer cell line, A549 with IC50 value of 2.53±0.07 μM, which was comparable to the standard doxorubicin (IC50=1.21±0.1 μM). Copyright © 2014 Elsevier Ltd. All rights reserved.

  19. Heat shock protein 27 mediates the effect of 1,3,5-trihydroxy-13,13-dimethyl-2H-pyran [7,6-b] xanthone on mitochondrial apoptosis in hepatocellular carcinoma.

    Science.gov (United States)

    Fu, Wei-ming; Zhang, Jin-fang; Wang, Hua; Xi, Zhi-chao; Wang, Wei-mao; Zhuang, Peng; Zhu, Xiao; Chen, Shih-chi; Chan, Tak-ming; Leung, Kwong-Sak; Lu, Gang; Xu, Hong-Xi; Kung, Hsiang-fu

    2012-08-03

    Hepatocellular carcinoma (HCC) is a global public health problem which causes approximately 500,000 deaths annually. Considering that the limited therapeutic options for HCC, novel therapeutic targets and drugs are urgently needed. In this study, we discovered that 1,3,5-trihydroxy-13,13-dimethyl-2H-pyran [7,6-b] xanthone (TDP), isolated from the traditional Chinese medicinal herb, Garcinia oblongifolia, effectively inhibited cell growth and induced the caspase-dependent mitochondrial apoptosis in HCC. A two-dimensional gel electrophoresis and mass spectrometry-based comparative proteomics were performed to find the molecular targets of TDP in HCC cells. Eighteen proteins were identified as differently expressed, with Hsp27 protein being one of the most significantly down-regulated proteins induced by TDP. In addition, the following gain- and loss-of-function studies indicated that Hsp27 mediates mitochondrial apoptosis induced by TDP. Furthermore, a nude mice model also demonstrated the suppressive effect of TDP on HCC. Our study suggests that TDP plays apoptosis-inducing roles by strongly suppressing the Hsp27 expression that is specifically associated with the mitochondrial death of the caspase-dependent pathway. In conclusion, TDP may be a potential anti-cancer drug candidate, especially to cancers with an abnormally high expression of Hsp27. Copyright © 2012 Elsevier B.V. All rights reserved.

  20. A Study on Spectro-Analytical Aspects, DNA - Interaction, Photo-Cleavage, Radical Scavenging, Cytotoxic Activities, Antibacterial and Docking Properties of 3 - (1 - (6 - methoxybenzo [d] thiazol - 2 - ylimino) ethyl) - 6 - methyl - 3H - pyran - 2, 4 - dione and its Metal Complexes.

    Science.gov (United States)

    Ravi, Mudavath; Chennam, Kishan Prasad; Ushaiah, B; Eslavath, Ravi Kumar; Perugu, Shyam; Ajumeera, Rajanna; Devi, Ch Sarala

    2015-09-01

    The focus of the present work is on the design, synthesis, characterization, DNA-interaction, photo-cleavage, radical scavenging, in-vitro cytotoxicity, antimicrobial, docking and kinetic studies of Cu (II), Cd (II), Ce (IV) and Zr (IV) metal complexes of an imine derivative, 3 - (1 - (6 - methoxybenzo [d] thiazol - 2 - ylimino) ethyl) - 6 - methyl - 3H - pyran - 2, 4 - dione. The investigation of metal ligand interactions for the determination of composition of metal complexes, corresponding kinetic studies and antioxidant activity in solution was carried out by spectrophotometric methods. The synthesized metal complexes were characterized by EDX analysis, Mass, IR, (1)H-NMR, (13)C-NMR and UV-Visible spectra. DNA binding studies of metal complexes with Calf thymus (CT) DNA were carried out at room temperature by employing UV-Vis electron absorption, fluorescence emission and viscosity measurement techniques. The results revealed that these complexes interact with DNA through intercalation. The results of in vitro antibacterial studies showed the enhanced activity of chelating agent in metal chelated form and thus inferring scope for further development of new therapeutic drugs. Cell viability experiments indicated that all complexes showed significant dose dependent cytotoxicity in selected cell lines. The molecular modeling and docking studies were carried out with energy minimized structures of metal complexes to identify the receptor to metal interactions.

  1. 6a-Nitro-6-(2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4′,5′-d]pyran-5-yl-6a,6b,7,8,9,11a-hexahydro-6H-spiro[chromeno[3,4-a]pyrrolizine-11,11′-indeno[1,2-b]quinoxaline

    Directory of Open Access Journals (Sweden)

    T. Anuradha

    2014-01-01

    Full Text Available In the title compound, C39H38N4O8, the quinoxaline and indene subunits are essentially planar, with maximum deviations of 0.071 (2 and 0.009 (2 Å, respectively. The indenoquinoxaline system forms a dihedral angle of 72.81 (3° with the chromenopyrrolizine system. The two dioxolane rings, as well as the pyran ring of the chromeno group and the terminal pyrrolizine, each adopt an envelope conformation with O and C as flap atoms. The central pyrrolizine ring adopts a twisted conformation. Intramolecular C—H...O and C—H...N hydrogen bonds occur. The crystal structure exhibits C—H...O hydrogen bonds, and is further stablized by C—H...π interactions, forming a two-dimensional network along the bc plane.

  2. Synthesis and characterization of a pentadentate Schiff base N3O2 ligand and its neutral technetium(V) complex. X-ray structure of (N,N'-3-azapentane-1,5-diylbis(3-(1-iminoethyl)-6-methyl-2H-pyran-2,4(3H)-dionato)(3-)-O,O',N,N',N double-prime)oxotechnetium(V)

    International Nuclear Information System (INIS)

    Shuang Liu; Rettig, S.J.; Orvig, C.

    1991-01-01

    Preparations of a potentially pentadentate ligand, N,N'-3-azapentane-1,5-diylbis(3-(1-iminoethyl)-6-methyl-2H-pyran-2,4-(3H)-dione) (H 3 apa), and its neutral technetium(V) complex, [TcO(apa)], are described. The 13 C and 1 H NMR, infrared, optical, and mass spectra of the pentadentate ligand and its technetium(V) complex are reported. The X-ray structure of [TcO(apa)] has been determined. Crystals are orthorhombic, space group Pbca, with a = 12.833 (2) angstrom, b = 33.320 (5) angstrom, c = 9.942(4) angstrom, V = 4251 (2) angstrom, and Z = 8. The structure was solved by Patterson and Fourier methods and was refined by full-matrix least-squares procedures to R = 0.028 and R W = 0.032 for 4054 reflections with I ≥ 3σ(I). The technetium(V) complex has a highly distorted octahedral coordination geometry comprising a [TcO] 3+ core and the triply deprotonated pentadentate ligand wrapping around the metal center. One of the two oxygen donor atoms of the pentadentate ligand is located trans to the Tc double-bond O bond while the remaining four donor atoms, N 3 O, occupy the equatorial sites. The distance between the deprotonated N(1) atom to the Tc center is significantly shorter than a normal Tc-N single bond length of 2.10 angstroms, but longer than that for a Tc-N triple bond. 1 H NMR spectral data reveal a rigid solution structure for the complex, which undergoes no conformational and configurational exchange at temperatures up to 50C

  3. 4-Hydroxy-6-methyl-3-[3-(thiophen-2-ylacryloyl]-2H-pyran-2-one

    Directory of Open Access Journals (Sweden)

    Salima Thabti

    2013-04-01

    Full Text Available The title compound, C13H10O4S, crystallizes with two molecules in the asymmetric unit in which the rings make dihedral angles of 3.9 (1 and 6.0 (1°; this planarity is due in part to the presence of an intramolecular O—H...O hydrogen bond, which generates an S(6 ring in each molecule. Both molecules represent E isomers with respect to the central C=C bond. In the crystal, molecules are linked by C—H...O interactions into a three-dimensional network.

  4. Diethyl 3H-naphtho[2,1-b]pyran-2,3-dicarboxylate

    Directory of Open Access Journals (Sweden)

    Abdullah Mohamed Asiri

    2009-04-01

    Full Text Available The sp3-hybridized methine C atom in the title compound, C19H18O5, lies out of the mean plane of the remaining 13 atoms of the naphthopyran fused-ring system by 0.571 (1 Å, and its H atom occupies a pseudo-equatorial site.

  5. 6-Hydroxymethyl-4-methoxy-2H-pyran-2-one (Opuntiol

    Directory of Open Access Journals (Sweden)

    Muhammad Athar Abbasi

    2010-01-01

    Full Text Available The title compound, C7H8O4, isolated from Opuntia dillenii Haw (Cactaceae, is almost planar [maximum deviation of 0.027 (2 Å] except for the H atoms of the methylene and methyl groups. The crystal packing is stabilized by C—H...O and O—H...O intermolecular hydrogen bonds, resulting in the formation of a three-dimensional network.

  6. Method to convert biomass to 5-(hydroxymethyl)-furfural (HMF) and furfural using lactones, furans, and pyrans as solvents

    Science.gov (United States)

    Dumesic, James A.; Ribeiro Gallo, Jean Marcel; Alonso, David

    2014-07-08

    Described is a process to produce hydroxymethyl furfural (HMF) from biomass-derived sugars. The process includes the steps of reacting a C5 and/or C6 sugar-containing reactant derived from biomass in a monophasic or biphasic reaction solution comprising water and a co-solvent. The co-solvent can be beta-, gamma-, and/or delta-lactones derived from biomass, tetrahydrofuran (THF) derived from biomass, and/or methyltetrahydrofuran (MTHF) derived from biomass. The reaction takes place in the presence of an acid catalyst and a dehydration catalyst for a time and under conditions such that at least a portion of glucose or fructose present in the reactant is converted to HMF.

  7. Bis(3-acetyl-6-methyl-2-oxo-2H-pyran-4-olatobis(dimethyl sulfoxidenickel(II

    Directory of Open Access Journals (Sweden)

    Amel Djedouani

    2009-10-01

    Full Text Available In the title compound, [Ni(C8H7O42{(CH32SO}2], the NiII atom is located on a crystallographic centre of symmetry and has a distorted octahedral coordination geometry of type MO6. The bidentate dehydroacetic acid (DHA ligands occupy the equatorial plane of the complex in a trans configuration, and the dimethyl sulfoxide (DMSO ligands are weakly coordinated through their O atoms in the axial positions.

  8. Condensed tannins: Base-catalysed reactions of polymeric procyanidins with toluene-α-thiol, liability of the interflavanoid bond and pyran ring

    Science.gov (United States)

    Peter E. Laks; Richard W. Hemingway

    1987-01-01

    Reaction of polymeric procyanidins (condensed tannins) with toluene-α-thiol at pH 12.0 and 23°C gave predominantly one stereoisomer of 1.3-bisbenzylthio-1-(3,4-dihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl) propan-2-ol (10) by stereoselective reaction at C-4 and C-2 of the Quinone methide derived from the upper 2,3-cis procyanidin units....

  9. (5S,6R-6-Bromo-6-methyl-5-phenyl-3,4,5,6-tetrahydro-2H-cyclopenta[b]pyran-7-one

    Directory of Open Access Journals (Sweden)

    Winai Ieawsuwan

    2011-10-01

    Full Text Available The title compound, C15H15BrO2, was synthesized by a Brønsted acid-catalysed domino electrocyclization-halogenation reaction. The five-membered ring is essentially planar (r.m.s. deviation 0.006 Å and forms a dihedral angle of 72.7 (3° with the attached phenyl ring. The six-membered heterocycle adopts a half-chair conformation. The crystal packing is stabilized by a C—H...O contact.

  10. Development of PhSCF2CF2SiMe3 as tetrafluoroethylene radical anion equivalent. Preparation of tetrafluoroethyl substituted alcohols and tetrafluoro-tetrahydro-pyrans

    Czech Academy of Sciences Publication Activity Database

    Beier, Petr; Chernykh, Yana; Klepetářová, Blanka

    2011-01-01

    Roč. 7, č. 13 (2011), s. 206-206 ISSN 1336-7242. [Zjazd Chemikov /63./. 05.09.2011-09.09.2011, Vysoké Tatry] R&D Projects: GA ČR GAP207/11/0421 Institutional research plan: CEZ:AV0Z40550506 Keywords : tetrafluoroethyl * tetrafluoroethylene * nucleophilic addition * radical addition Subject RIV: CC - Organic Chemistry

  11. Oligomeric flavanoids. Part 15a. Base-catalyzed pyran rearrangements of procyanidin B-2, and evidence for the oxidative transformation of B- to A-type procyanidins

    Science.gov (United States)

    Johann F.W. Burger; Herbert Kolodziej; Richard W. Hemingway; Jan P. Steynberg; Desmond A. Young; Daneel Ferreira

    1990-01-01

    Procyanidin B-2 3 is subject to facile C-ring isomerizations in 0.1M NaHCO3 solution to form a novel series of 3,4,9,1o-tetrahydro-2H,8H-pyrano[2,3-h]chromenes 7, 9, and 10. The low percentage conversion of B- to A-...

  12. An assessment of the genotoxicity and human health risk of topical use of kojic acid [5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one].

    Science.gov (United States)

    Nohynek, Gerhard J; Kirkland, David; Marzin, Daniel; Toutain, Herve; Leclerc-Ribaud, Christele; Jinnai, Hiroyuki

    2004-01-01

    Kojic acid (KA), a natural substance produced by fungi or bacteria, such as Aspergillus, Penicillium or Acetobacter spp, is contained in traditional Japanese fermented foods and is used as a dermatological skin-lightening agent. High concentrations of KA (>or=1000 microg/plate) were mutagenic in S. typhimurium strains TA 98, TA 100, TA 1535, TA102 and E. coli WP2uvrA, but not in TA 1537. An Ames test following the "treat and plate" protocol was negative. A chromosome aberration test in V79 cells following a robust protocol showed only a marginal increase in chromosome aberrations at cytotoxic concentrations after prolonged (>or=18 h) exposure. No genotoxic activity was observed for hprt mutations either in mouse lymphoma or V79 cells, or in in vitro micronucleus tests in human keratinocytes or hepatocytes. All in vivo genotoxicity studies on KA doses were negative, including mouse bone marrow micronucleus tests after single or multiple doses, an in vivo/in vitro unscheduled DNA synthesis (UDS) test, or a study in the liver of the transgenic Muta(TM) Mouse. On the basis of pharmacokinetic studies in rats and in vitro absorption studies in human skin, the systemic exposure of KA in man following its topical application is estimated to be in the range of 0.03-0.06 mg/kg/day. Comparing these values with the NOAEL in oral subchronic animal studies (250 mg/kg/day), the calculated margin of safety would be 4200- to 8900-fold. Comparing human exposure with the doses that were negative for micronuclei, UDS and gene mutations in vivo, the margins of safety are 16000 to 26000-fold. In conclusion, the topical use of KA as a skin lightening agent results in minimal exposure that poses no or negligible risk of genotoxicity or toxicity to the consumer.

  13. Simultaneous quantification of differently glycosylated, acetylated and 2,3-dihydro-2,5-dihydroxy-6-methyl-4h-pyran-4-one-conjugated soyasaponins using reversed-phase high-performance liquid chromatography with evaporative light scattering detection

    NARCIS (Netherlands)

    DeCroos, K.; Vincken, J.P.; Heng, L.; Bakker, R.; Gruppen, H.; Verstraete, W.

    2005-01-01

    A novel method utilizing high-performance liquid chromatography (HPLC) with evaporative light scattering detection (ELSD) and electrospray ionisation mass spectrometry (ESI-MS) was developed for the analysis of soyasaponins, a divers group of triterpenic compounds with one or two sugar side chains,

  14. Hydroquinone analog 4-[(Tetrahydro-2H-pyran-2‑yl) oxy] phenol induces C26 colon cancer cell apoptosis and inhibits tumor growth in vivo.

    Science.gov (United States)

    Du, Qigen; Xin, Guang; Niu, Hai; Huang, Wen

    2015-06-01

    The 4[(Tetrahydro‑2H‑pyran‑2‑yl) oxy] phenol (XG‑d) hydroquinone analog, is found in Vaccinium vitis‑idaea  L. Although it is known for its antioxidant properties and high level of safety, its antitumor activity remains to be elucidated. In the present study, the anticancer effect of XG‑d was determined in vitro and in vivo. The cytotoxicity of XG‑d against C26 murine colon carcinoma cells was found to occur in a time‑ and concentration‑dependent manner, whereas little effect was observed in the two normal cell lines (HK‑2 and L02) investigated. Oral administration of XG‑d (100 mg/kg) had effects on the tumor growth of tumor‑bearing mice. Furthermore, marked apoptosis was observed using Hoechst 33258 staining and flow cytometric analysis with annexin V/propidium iodide double staining. XG‑d also downregulated the expression of B‑cell lymphoma 2 (Bcl‑2), increased the expression levels of Bcl‑2‑associated X protein and activated caspase‑9, caspase‑3 and poly(adenosine diphosphate‑ribose) polymerase. The present study demonstrated for the first time, to the best of our knowledge, that XG‑d inhibited cancer cell growth via the induction of apoptosis and was also able to inhibit tumor growth in vivo. These results demonstrated that XG‑d may be used as a potential natural agent for cancer therapy with low toxicity.

  15. Methyl 5,7-dihydroxy-2,2,9-trimethyl-6,11-dioxo-6,11-dihydro-2H-anthra[2,3-b]pyran-8-carboxylate

    Directory of Open Access Journals (Sweden)

    Annelise Lobstein

    2008-12-01

    Full Text Available The title compound, C22H18O7, also known as laurentiquinone B, is a new anthraquinone which was isolated from Vismia laurentii, a Cameroonian medicinal plant. The asymmetric unit contains two independent molecules. Each of them contains four fused rings, three of which are coplanar and typical of anthracene, while the heterocyclic rings adopt envelope conformations. Intramolecular O—H...O hydrogen bonds result in the formation of two planar rings, which are also almost coplanar with the adjacent rings. In the crystal structure, intermolecular O—H...O and C—H...O hydrogen bonds link the molecules and a π–π contact is also present [centroid-centroid distance = 3.967 (3 Å].

  16. pyrroles

    Indian Academy of Sciences (India)

    and various aldehydes to afford 4H-pyrano[3,2-b]pyrrole derivatives in moderate to good yield using ferric .... (pyran C5), 122.8, 122.4, 128.9, 132.7, 133.0, 141.6. (Ar-C), 179.0 (pyran C2). 2.2f ..... After Michael-type addition of malononitrile.

  17. Crystal structure of bis{μ2-2,2′-[(4,10-dimethyl-1,4,7,10-tetraazacyclododecane-1,7-diylbis(methylene]bis(4-oxo-4H-pyran-3-olato}dicobaltcalcium bis(perchlorate 1.36-hydrate

    Directory of Open Access Journals (Sweden)

    Patrizia Rossi

    2017-12-01

    Full Text Available The title compound, [CaCo2(C22H30N4O62](ClO42·1.36H2O or {Ca[Co(H–2L1]2}·2ClO4·1.36H2O {where L1 is 4,10-bis[(3-hydroxy-4-pyron-2-ylmethyl]-1,7-dimethyl-1,4,7,10-tetraazacyclododecane}, is a trinuclear complex whose asymmetric unit comprises a quarter of the {Ca[Co(H–2L1]2}2+ trinuclear complex, half of a perchlorate ion and 0.34-water molecules. In the neutral [Co(H–2L1] moiety, the cobalt ion is hexacoordinated in a trigonal–prismatic fashion by the surrounding N4O2 donor set. A Ca2+ cation holds together two neutral [Co(H–2L1] moieties and is octacoordinated in a distorted trigonal–dodecahedral fashion by the surrounding O atoms belonging to the deprotonated oxide and carbonyl groups of two [Co(H–2L1] units. The coordination of the CoII cation preorganizes L1 and an electron-rich area forms, which is able to host hard metal ions. The comparison between the present structure and the previously published ones suggests a high versatility of this ligand; indeed, hard metal ions with different nature and dimensions lead to complexes having different stoichiometry (mono- and dinuclear monomers and trinuclear dimers or even a polymeric structure. The heterotrinuclear CoII–CaII–CoII complexes are connected in three dimensions via weak C—H...O hydrogen bonds, which are also responsible for the interactions with the perchlorate anions and the lattice water molecules. The perchlorate anion is disordered about a twofold rotation axis and was refined giving the two positions a fixed occupancy factor of 0.5. The crystal studied was refined as a two-component inversion twin [BASF parameter = 0.14 (4].

  18. Plasma levels of d1-3-(1,1-dimethylheptyl)-6,6aβ,7,8,10,10aα-hexahydro-1-hydroxy-6,6-dimethyl-9H-dibenzo[b,d]pyran-9-one (Lilly 109514) by quantitative mass fragmentography

    International Nuclear Information System (INIS)

    Sullivan, H.R.; Kau, D.L.K.; Wood, P.G.

    1975-01-01

    Lilly compound 109514 produces alterations in behavioral parameters in laboratory animals. Its relaxant and sedative properties are being studied clinically. A quantitative mass fragmentography (QMF) method for Lilly 109514 has been developed which is sensitive to 2 pmoles/4 ml sample. A similar assay has been developed for the major metabolite (formed by reduction of the 9-keto group). Both assays use deuterium labeled internal standards. Plasma concentrations of the parent drug and the metabolite were determined in dogs following oral administration of single and multiple 400 μg/kg doses of Lilly 109514. Results indicated the drug to be rapidly absorbed and metabolized in this species. Concentrations of the metabolite were significantly higher than those of the parent drug. These results implied that multiple-dosing of Lilly 109514 did not cause induction of metabolizing enzymes or other alterations of the metabolic process in the dog. Determination of the plasma concentrations of the parent drug and metabolite following i.v. administration have permitted the calculation of bioavailability and absorption data. The ability to follow plasma levels for 48 hours after a single i.v. administration of 100 μg/kg of 109514 graphically illustrates the value of quantitative mass fragmentography in kinetic studies of cannabinoids

  19. Design and Discovery of N -(2-Methyl-5'-morpholino-6'-((tetrahydro-2 H -pyran-4-yl)oxy)-[3,3'-bipyridin]-5-yl)-3-(trifluoromethyl)benzamide (RAF709): A Potent, Selective, and Efficacious RAF Inhibitor Targeting RAS Mutant Cancers

    Energy Technology Data Exchange (ETDEWEB)

    Nishiguchi, Gisele A.; Rico, Alice; Tanner, Huw; Aversa, Robert J.; Taft, Benjamin R.; Subramanian, Sharadha; Setti, Lina; Burger, Matthew T.; Wan, Lifeng; Tamez, Victoriano; Smith, Aaron; Lou, Yan; Barsanti, Paul A.; Appleton, Brent A.; Mamo, Mulugeta; Tandeske, Laura; Dix, Ina; Tellew, John E.; Huang, Shenlin; Griner, Lesley A. Mathews; Cooke, Vesselina G.; Van Abbema, Anne; Merritt, Hanne; Ma, Sylvia; Gampa, Kalyani; Feng, Fei; Yuan, Jing; Wang, Yingyun; Haling, Jacob R.; Vaziri; #8741; , Sepideh; Hekmat-Nejad, Mohammad; Jansen, Johanna M.; Polyakov, Valery; Zang, Richard; Sethuraman, Vijay; Amiri, Payman; Singh, Mallika; Lees, Emma; Shao, Wenlin; Stuart, Darrin D.; Dillon, Michael P.; Ramurthy, Savithri (Novartis)

    2017-06-06

    RAS oncogenes have been implicated in >30% of human cancers, all representing high unmet medical need. The exquisite dependency on CRAF kinase in KRAS mutant tumors has been established in genetically engineered mouse models and human tumor cells. To date, many small molecule approaches are under investigation to target CRAF, yet kinase-selective and cellular potent inhibitors remain challenging to identify. Herein, we describe 14 (RAF709) [Aversa, Biaryl amide compounds as kinase inhibitors and their preparation. WO 2014151616, 2014], a selective B/C RAF inhibitor, which was developed through a hypothesis-driven approach focusing on drug-like properties. A key challenge encountered in the medicinal chemistry campaign was maintaining a balance between good solubility and potent cellular activity (suppression of pMEK and proliferation) in KRAS mutant tumor cell lines. We investigated the small molecule crystal structure of lead molecule 7 and hypothesized that disruption of the crystal packing would improve solubility, which led to a change from N-methylpyridone to a tetrahydropyranyl oxy-pyridine derivative. 14 proved to be soluble, kinase selective, and efficacious in a KRAS mutant xenograft model.

  20. Three new compounds from the marine fungus Penicillium sp.

    Science.gov (United States)

    Wu, Hong-Hua; Tian, Li; Feng, Bao-Min; Li, Zhi-Feng; Zhang, Qi-Hui; Pei, Yue-Hu

    2010-01-01

    Continuous research on the ethyl acetate extract of the fermentation broth of the marine fungus Y26-02 (Penicillium sp.) led to the purification of one known and three new compounds. Their structures were elucidated, respectively, as butyl 2-(4-oxo-5,6-dihydro-2H-pyran-3-yl) acetate (1), 4-hydroxyphenethyl 2-(4-oxo-5,6-dihydro-2H-pyran-3-yl) acetate (2), 3-hydroxybenzyl 2-(4-oxo-5,6-dihydro-2H-pyran-3-yl) acetate (3), and desoxypatulinic acid (4) on the basis of their spectroscopic and physico-chemical properties.

  1. The chemistry of furazans fused to six- and seven-membered heterocycles with one heteroatom

    International Nuclear Information System (INIS)

    Sheremetev, Aleksei B

    1999-01-01

    The data on the synthesis and properties of furazan derivatives fused with pyridine, pyran, thiopyran, azepine and thiepine rings are surveyed and described systematically. The bibliography includes 85 references.

  2. DABCO catalyzed synthesis of new 2-amino-8-arylidene-4-aryl-5,6,7 ...

    African Journals Online (AJOL)

    tetrahydrobenzo-4H-pyran-3-carbonitriles from the reaction of α,ά-bis(substituted benzylidene)cycloalkanones with malononitrile under reflux conditions in the presence DABCO in good to excellent yields has been described. KEY WORDS: DABCO ...

  3. 5-Fluoro-6′H,7′H,8′H-spiro[indoline-3,7′-pyrano[3,2-c:5,6-c′]di-1-benzopyran]-2,6′,8′-trione

    Directory of Open Access Journals (Sweden)

    J. Suresh

    2012-03-01

    Full Text Available In the title compound, C26H12FNO6, the central pyran ring and both benzopyran systems are nonplanar, having total puckering amplitudes of 0.139 (2, 0.050 (1 and 0.112 (2 Å, respectively. The central pyran ring adopts a boat conformation. The crystal structure is stabilized by C—H...O, N—H...O, N—H...F and C—H...π interactions.

  4. 6-Methyl-2-pyridyl N-acetyl-1-thio-β-d-glucosa-minide methanol monosolvate.

    Science.gov (United States)

    Chen, Bo; Guo, Miao; Jin, Wei-Hua; Wang, Yan-Wei; Liang, Hong-Ze

    2010-09-15

    In the title compound, C(14)H(20)N(2)O(5)S·CH(4)O, the pyran-ose and pyridine rings are linked through an S atom. The pyran-ose ring has a normal chair conformation. An intra-molecular O-H⋯N hydrogen bond occurs. Inter-molecular O-H⋯O, N-H⋯O, O-H⋯N and weak C-H⋯O hydrogen bonding is present in the crystal structure.

  5. 1,5-Anhydro-D-fructose as Chiral Building Block: A Novel Approach to 1-Deoxymannojirimycin

    DEFF Research Database (Denmark)

    Maier, Peter; Andersen, Søren Møller; Lundt, Inge

    2006-01-01

    A novel six-step synthesis of 1-deoxymannojirimycin from 1,5-anhydro-D-fructose in 35% overall yield is reported. The key steps are nucleophilic piperidine ring formation and subsequent Lewis acid induced pyran ether cleavage.......A novel six-step synthesis of 1-deoxymannojirimycin from 1,5-anhydro-D-fructose in 35% overall yield is reported. The key steps are nucleophilic piperidine ring formation and subsequent Lewis acid induced pyran ether cleavage....

  6. Kavalactones and benzoic acid derivatives from leaves of Piper fuligineum Kunth (Piperaceae)

    Energy Technology Data Exchange (ETDEWEB)

    Mazzeu, Bruna F.; Felippe, Lidiane G.; Furlan, Maysa, E-mail: maysaf@iq.unesp.br [Universidade Estadual Paulista Julio de Mesquita Filho (UNESP), Araraquara, SP (Brazil); Cotinguiba, Fernando [Universidade Federal do Rio de Janeiro (IPPN/UFRJ), Rio de Janeiro, RJ (Brazil). Instituto de Pesquisas de Produtos Naturais; Kato, Massuo J. [Universidade de São Paulo (USP), SP (Brazil). Instituto de Química

    2018-05-01

    The known kavalactones (E)-4-methoxy-6-styryl-2H-pyran-2-one, 4-methoxy6-(3-phenyloxiran-2-yl)-2H-pyran-2-one, 6-(1,2-dihydroxy-2-phenylethyl)-4-methoxy-2H-pyran2-one, the three benzoic acid derivatives methyl-4-methoxy-3-(3'-methyl-2'-butenyl)benzoate and methyl 2,2-dimethyl-4-oxochroman-6-carboxylate, and a new methyl 4-methoxy-3-(3-methylbut2-enoyl)benzoate were isolated from the ethanolic extract of Piper fuligineum. The structures of these compounds were determined by using a combination of spectroscopic methods, including 1D- and 2D-nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry. This is the first report of the chemical study of P. fuligineum, and the methyl 4-methoxy-3-(3-methylbut2-enoyl)benzoate is described as a new natural product. (author)

  7. Comparative Chemical Analysis of the Essential Oil Constituents in the Bark, Heartwood and Fruits of Cryptocarya massoy (Oken Kosterm. (Lauraceae from Papua New Guinea

    Directory of Open Access Journals (Sweden)

    David N. Leach

    2007-02-01

    Full Text Available Exhaustive hydro-distillation of the bark, heartwood and fruits of Cryptocarya massoy (Lauraceae afforded pale yellow-coloured oils in 0.7, 1.2 and 1.0 % yields, respectively. Detailed chemical evaluation of these distillates using GC/MS revealed the major components in the bark and the heartwood oils to be the C-10 (5,6-dihydro-6-pentyl-2H-pyran-2-one and C-12 (5,6-dihydro-6-heptyl-2H-pyran-2-one massoia lactones, while the major fruit oil constituent was benzyl benzoate (68.3 %. The heartwood also contained trace amounts of the C-14 (5,6-dihydro-6-nonyl-2H-pyran-2-one massoia lactone (1.4 % and the saturated C-10 derivative d-decalactone (2.5 %.

  8. Methyl 2-(2,2-dimethyl-3a,6a-dihydrofuro[3,2-d][1,3]dioxol-5-yl-4-oxo-4H-chromene-3-carboxylate

    Directory of Open Access Journals (Sweden)

    Devadasan Velmurugan

    2013-08-01

    Full Text Available In the title molecule, C18H16O7, the dioxolane ring adopts an envelope conformation with the dimethyl-substituted C atom as the flap. The furan ring is almost coplanar with the pyran ring, with a dihedral angle of 1.04 (10° between the planes, and it makes a dihedral angle of 67.97 (11° with the mean plane of the dioxolane ring. The latter makes a dihedral angle of 67.15 (10° with the pyran ring. The O atom attached to the pyran ring deviates by −0.009 (1 Å. The crystal packing features C—H...O hydrogen bonds, forming a three-dimensional structure. The methoxycarbonyl atoms are disordered over two positions, with a refined occupancy ratio of 0.508 (18:0.492 (18.

  9. rac-Dimethyl 2-(tert-butylamino-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3,4-dicarboxylate

    Directory of Open Access Journals (Sweden)

    S. Antony Inglebert

    2011-11-01

    Full Text Available The title compound, C20H21NO7, is asymmetric with a chiral centre located in the pyran ring and crystallizes as a racemate. The molecular framework is somewhat bent; the coumarin moiety and the pyran ring are inclined by 7.85 (5°. The molecular structure is characterized by an intramolecular N—H...O hydrogen bond, which generates an S(6 ring motif, and the crystal packing is stabilized by intermolecular C—H...O hydrogen bonds. The 3-carboxylate O atom is involved in both of them, having a bifurcated character.

  10. 6-Methyl-2-pyridyl N-acetyl-1-thio-β-d-glucosa­minide methanol monosolvate

    Science.gov (United States)

    Chen, Bo; Guo, Miao; Jin, Wei-Hua; Wang, Yan-Wei; Liang, Hong-Ze

    2010-01-01

    In the title compound, C14H20N2O5S·CH4O, the pyran­ose and pyridine rings are linked through an S atom. The pyran­ose ring has a normal chair conformation. An intra­molecular O—H⋯N hydrogen bond occurs. Inter­molecular O—H⋯O, N—H⋯O, O—H⋯N and weak C—H⋯O hydrogen bonding is present in the crystal structure. PMID:21587547

  11. Unprecedented Oxidative Addition of Highly Active Manganese into the Oxygen-Sulfur Bond of Coumarin and Pyrone 4-Tosylates

    Energy Technology Data Exchange (ETDEWEB)

    Shin, Ueon Sang; Joo, Seong-Ryu; Kim, Seung-Hoi [Dankook University , Cheonan (Korea, Republic of)

    2016-06-15

    Novel organomanganese reagents, 2-oxo-2H-chromen-4-yloxy tosylmanganese (A1), and 6-methyl-2-oxo-2H-pyran-4-yloxy tosylmanganese (A2), were obtained by the reaction of highly active Mn with 2-oxo-2H-chromen-4-yl 4-methylbenzenesulfonate (I) and 6-methyl-2-oxo-2H-pyran-4-yl-4-methylbenzenesulfonate (II), respectively. This was accomplished by the insertion of Mn into the oxygen-sulfur bond. Of interest, subsequent cross-coupling reactions of the thus-obtained organomanganese reagents afforded two different products, esters and sulfones, depending on the electrophile used under mild conditions.

  12. 8-Chloro-4-oxo-4H-chromene-3-carbaldehyde

    Directory of Open Access Journals (Sweden)

    Yoshinobu Ishikawa

    2014-07-01

    Full Text Available In the title compound, C10H5ClO3, a chlorinated 3-formylchromone derivative, all atoms are essentially coplanar (r.m.s. deviation = 0.032 Å for the non-H atoms, with the largest deviation from the least-squares plane [0.0598 (14 Å] being for a pyran-ring C atom. In the crystal, molecules are linked through stacking interactions along the b axis [shortest centroid–centroid distance between the pyran and benzene rings = 3.566 (2 Å].

  13. A versatile route to benzodiazocine and spiropyran derivatives ...

    Indian Academy of Sciences (India)

    The photolytic reaction with trans-stilbene resulted in the exclusive formation of spiro{2 ,5 ,6 -triphenyl-2H-pyran-. 4 ,3}-benzo[b]thiophene-2-one derivatives. Theoretical calculations have been performed to study the mecha- nism and stereoselectivity of products. Good yield and broad scope of usable substrates of industrial ...

  14. Journal of Chemical Sciences | Indian Academy of Sciences

    Indian Academy of Sciences (India)

    The photolytic reaction with trans-stilbene resulted in the exclusive formation of spiro{2',5',6'-triphenyl-2H-pyran-4',3}-benzo[b]thiophene-2-one derivatives. Theoretical calculations have been performed to study the mechanism and stereoselectivity of products. Good yield and broad scope of usable substrates of industrial ...

  15. Investigating the Influence of Karrikins on Seed Germination

    Science.gov (United States)

    de Beer, Josef

    2012-01-01

    Recent research has identified a karrikin (a butenolide derative) known as 3-methyl-2H-furo[2,3-c]pyran-2-one, formed from burning cellulose, that stimulates seed germination. Here, I present ideas on how to investigate the influence of karrikins on seed germination in the laboratory.

  16. Stability of pea DDMP saponin and the mechanism of its decomposition

    NARCIS (Netherlands)

    Heng, L.; Vincken, J.P.; Hoppe, K.; Koningsveld, van G.A.; DeCroos, K.; Gruppen, H.; Boekel, van M.A.J.S.; Voragen, A.G.J.

    2006-01-01

    DDMP saponin can be converted to saponin B by the loss of its DDMP group (2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one). The stability of DDMP saponin from pea was investigated under various conditions (temperature, ethanol concentration, pH). DDMP saponin in water was observed to be unstable

  17. Bitterness of saponins and their content in dry peas

    NARCIS (Netherlands)

    Heng, L.; Vincken, J.P.; Koningsveld, van G.A.; Legger, A.; Gruppen, H.; Boekel, van M.A.J.S.; Roozen, J.; Voragen, A.G.J.

    2006-01-01

    The bitterness of a saponin mixture (containing saponin B and DDMP (2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one) saponin in a ratio of 1:4) and saponin B obtained from dry peas were established by a trained panel using line scaling. Both saponins were found to be bitter. However, the saponin

  18. SYNTHESIS AND IN VITRO ANTIMICROBIAL EVALUATION OF 5 ...

    African Journals Online (AJOL)

    Preferred Customer

    creation of molecular diversity and complexity [1-3]. One of the main challenges in medicinal chemistry is the design and synthesis of biologically active molecules. 4H-pyran play an essential role as biologically active compounds and represent an interesting template for medicinal chemistry. Many of these compounds are.

  19. Chemical components of Vellozia stipitata

    International Nuclear Information System (INIS)

    Cunha Pinto, A. da; Zocher, D.H.T.; Gonzaga, L.; Pinchin, R.; Lopes, C.C.

    From the hexane extract of the root and stem of Vellozia stipitata(Family Velloziaceae), are isolated lupenone, lupeol, vellozone, 22-hydroxy-21αH-hopan-3-one and 4,5,10,11-tetrahydro-3,8,8-trimethylphenanthro [10,1-bc] pyran-9(8H)-one. (Author) [pt

  20. High Excitation Transfer Efficiency from Energy Relay Dyes in Dye-Sensitized Solar Cells

    KAUST Repository

    Hardin, Brian E.; Yum, Jun-Ho; Hoke, Eric T.; Jun, Young Chul; Péchy, Peter; Torres, Tomás; Brongersma, Mark L.; Nazeeruddin, Md. Khaja; Grätzel, Michael; McGehee, Michael D.

    2010-01-01

    The energy relay dye, 4-(Dicyanomethylene)-2-methyl-6-(4- dimethylaminostyryl)-4H-pyran (DCM), was used with a near-infrared sensitizing dye, TT1, to increase the overall power conversion efficiency of a dye-sensitized solar cell (DSC) from 3

  1. Enzymatic production of microthecin by aldos-2-ulose dehydratase from 1,5-anhydro-D-fructose and stability studies of microthecin

    DEFF Research Database (Denmark)

    Yu, Shukun; Andreassen, Mikkel; Lundt, Inge

    2008-01-01

    Microthecin (2-hydroxy-2-(hydroxymethyl)-2H-pyran-3(6H)-one), which has anti-microbial activity, is one of the end products of an alternative glycogen and starch degrading pathway, the anhydrofructose pathway. It is formed from 1,5- anhydro-D-fructose (AF), a product of a-1,4-glucan lyase (EC 4...

  2. Configuration-dependent conformational transmission in trigonal-bipyramidal phosphorus(V) compounds. Enhanced gauche (-) population around the C(5)-C(6) linkage in 6-phosphorus(V) phosphorylated tetramethyl-a-D-galactopyranoside

    NARCIS (Netherlands)

    Vries, de N.K.; Buck, H.M.

    1986-01-01

    A 300-MHz 1H NMR variable-temperature study of the 1'-phosphorylated trigonal-bipyramidal (TBP) tetrahydropyran-2-methyl model compound 4 is reported. For this compound, in which both the equatorial and axial sites undergoing phosphorus pseudorotation bear a tetrahydro-pyran-2-methyl group, a

  3. Do fire-related cues, including smoke-water, karrikinolide, glyceronitrile and nitrate, stimulate the germination of 17 Anigozanthos taxa and Blancoa canescens (Haemodoraceae)?

    Czech Academy of Sciences Publication Activity Database

    Downes, K. S.; Light, M. E.; Pošta, Martin; Kohout, Ladislav; Staden van, J.

    2014-01-01

    Roč. 62, č. 4 (2014), s. 347-358 ISSN 0067-1924 Institutional support: RVO:61388963 Keywords : kangaroo paw * KAR(1) * morphophysiological dormancy * underdeveloped embryos * 2,3-dihydroxypropanenitrile * 3-methyl-2H-furo[2,3-c]pyran-2-one Subject RIV: CC - Organic Chemistry Impact factor: 1.355, year: 2014

  4. PbO as an efficient and reusable catalyst for one-pot synthesis of ...

    Indian Academy of Sciences (India)

    using open capillary tubes on Veego melting point appa- ratus and are uncorrected. FTIR spectra were recorded on Shimadzu 8400 s spectrometer using KBr pellets. 1H .... condensation reactions.42,43 We report here facile syn- thesis of tetrahydrobenzo pyrans and benzylidene malo- nitriles by grinding under solvent-free ...

  5. Condensed tannins: Quinone methide intermediates in procyanidin synthesis

    Science.gov (United States)

    Richard W. Hemingway; L. Y. Foo

    1983-01-01

    Proanthocyanidins (condensed tanruns) are widely distributed in plants and are found in sufficiently high concentration in some tree barks to encourage their industrial utilization. These polymers consist of flavanoid units linked through the C-4 of the pyran ring to the C-6 or C-8 carbons of the aromatic A-ring. Recent advances in the chemistry of condensed tannins...

  6. Author Details

    African Journals Online (AJOL)

    pot, Four-component Synthesis of 2-Amino-3-Cyanopyridines Abstract PDF · Vol 63 (2010) - Articles Polyaniline/SiO2 Catalyzed One-pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives Abstract PDF. ISSN: 0379-4350. AJOL African Journals ...

  7. Acid-catalyzed rearrangements of flavan-4-phloroglucinol derivatives to novel 6-hydroxyphenyl-6a,llb-dihydro-6H-[1]benzofuro[2,3-c]-chromenes and hydroxyphenyl-3,2'-spirobi[dihydro[l]benzofurans

    Science.gov (United States)

    Petrus J. Steynberg; Jan P. Steynberg; Richard W. Hemingway; Daneel Ferreira; G. Wayne McGraw

    1997-01-01

    Acetic acid-catalyzed cleavage of proanthocyanidins in the presence of phloroglucinol gives a series of 2R procyanidin- and prodelphinidin-phloroglucinol adducts together with a novel 2S all-cis derivative implicating cleavage of the pyran ring and subsequent inversion of stereochernistry at C-2c. These flavan-4-phloroglucinol adducts also suffer dehydration to...

  8. Expedient Access to an N-phenylpyrrolidin-2-yl Heterocycle via a ...

    African Journals Online (AJOL)

    NICO

    Milder bases were employed catalytically for the 1,4-conjugate addition of ... using 2-bromoaniline given that it was available in our labora- tory and ... Scheme 3. Base-catalysed intramolecular aza-Michael reaction of indoles containing pendant-conjugated esters. Scheme 4. Synthesis of pyran-2-ol. Scheme 5. Synthesis of ...

  9. A New Synthetic Route to Dihydrobenzopyran Via Tandem Demethylation Cyclisation

    Directory of Open Access Journals (Sweden)

    G. Shanmugam

    2000-06-01

    Full Text Available A tandem demethylation-cyclisation reaction resulting in the formation of pyran rings using AlCl3/EtSH reagent under mild reaction conditions is reported. X-ray diffraction studies on the intermediate support the suggested mechanism.

  10. Highly efficient solvent-free synthesis of pyranopyrazoles by a ...

    Indian Academy of Sciences (India)

    bDepartment of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, P.O. Box 91775, ... key advantages of this process are high yields, shorter reaction times, easy work-up, ... ing pyran derivatives and hydrazine hydrate,9 use of.

  11. Pericocins A-D, New Bioactive Compounds from Periconia sp.

    Science.gov (United States)

    Wu, Yue-Hua; Xiao, Gao-Keng; Chen, Guo-Dong; Wang, Chuan-Xi; Hu, Dan; Lian, Yun-Yang; Lin, Feng; Guo, Liang-Dong; Yao, Xin-Sheng; Gao, Hao

    2015-12-01

    One new dihydroisocoumarin, pericocin A (1), one new chromone, pericocin B (2), and two new α-pyrone derivatives, pericocins C-D (3-4), together with two known compounds, 3-(2-oxo-2H-pyran-6-yl)propanoic acid (5) and (E)-3-(2-oxo-2H-pyran-6-yl)acrylic acid (6), were isolated from the culture of the endolichenic fungus Periconia sp.. Their structures were elucidated by spectroscopic methods. All these compounds are derived from the polyketone biosynthetic pathway. Compound 1 was obtained as a mixture of enantiomers. The antimicrobial activity of compounds 1-5 was tested against Escherichia coli, Staphylococcus aureus, Aspergillus niger, and Candida albicans. Compounds 1-5 showed moderate antimicrobial activity against A. niger and weak activity against C. albicans.

  12. Iridoids from leaf extract of Genipa americana

    Directory of Open Access Journals (Sweden)

    Jovelina S.F. Alves

    Full Text Available Abstract Genipa americana L., Rubiaceae, is a plant native from Brazil popularly known as “jenipapo”. Two iridoids, 1-hydroxy-7-(hydroxymethyl-1,4aH,5H,7aH-cyclopenta[c]pyran-4-carbaldehyde (1, and iridoid 7-(hydroxymethyl-1-methoxy-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carbaldehyde (2 were isolated and identified in the leaf extract of G. americana. Compounds 1 and 2 were identified for the first time in G. americana, and 1 has not been yet described in literature. These substances were analyzed by spectroscopic techniques such as infrared, high resolution mass spectrometry, 1H and 13C 1D; as well as 2D nuclear magnetic resonance. Moreover, the presence of flavonoids was detected by a preliminary analysis by Thin Layer Chromatography.

  13. Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes

    Directory of Open Access Journals (Sweden)

    Philipp Röse

    2015-01-01

    Full Text Available The cobalt(I-catalysed 1,4-hydrovinylation reaction of allyloxytrimethylsilane and allyl alcohol with substituted 1,3-dienes leads to hydroxy-functionalised 1,4-dienes in excellent regio- and diastereoselective fashion. Those 1,4-dienols can be converted into tetrahydrofuran and pyran derivatives under indirect electrochemical conditions generating selenium or iodonium cations. The reactions proceed in good yields and regioselectivities for the formation of single diastereomers.

  14. α-d-Tagatopyran­ose

    Science.gov (United States)

    Punzo, Francesco; Watkin, David J.; Fleet, George W. J.

    2009-01-01

    The title compound, C6H12O6, also known as d-Tagatose, occurs in its furanose and pyranose forms in solution, but only the α-pyran­ose form crystallizes out. In the crystal, the molecules form hydrogen bonded chains propagating in [100] linked by O—H⋯O interactions. Further O—H⋯O bonds cross-link the chains. PMID:21583239

  15. The relationship between the violet pigment PP-V production and intracellular ammonium level in Penicillium purpurogenum

    OpenAIRE

    Kojima, Ryo; Arai, Teppei; Matsufuji, Hiroshi; Kasumi, Takafumi; Watanabe, Taisuke; Ogihara, Jun

    2016-01-01

    Penicillium purpurogenum is the fungus that produces an azaphilone pigment. However, details about the pigment biosynthesis pathway are unknown. The violet pigment PP-V is the one of the main pigments biosynthesized by this fungus. This pigment contains an amino group in a pyran ring as its core structure. We focused on this pigment and examined the relationship between intracellular ammonium concentration and pigment production using glutamine as a nitrogen source. The intracellular ammonium...

  16. Deoxyarbutin Possesses a Potent Skin-Lightening Capacity with No Discernible Cytotoxicity against Melanosomes

    OpenAIRE

    Miao, Fang; Shi, Ying; Fan, Zhi-Feng; Jiang, Shan; Xu, Shi-Zheng; Lei, Tie-Chi

    2016-01-01

    Safe and effective ingredients capable of removing undesired hyperpigmentation from facial skin are urgently needed for both pharmaceutical and cosmetic purposes. Deoxyarbutin (4-[(tetrahydro-2H-pyran-2-yl) oxy] phenol, D-Arb) is a glucoside derivative of hydroquinone. Here, we investigated the toxicity and efficacy of D-Arb at the sub-cellular level (directly on melanosomes) and skin pigmentation using in vivo and in vitro models to compare with its parent compound hydroquinone (1,4-benzened...

  17. Experimental and Computational Study of an Unexpected Iron-Catalyzed Carboetherification by Cooperative Metal and Ligand Substrate Interaction and Proton Shuttling

    KAUST Repository

    El-Sepelgy, Osama; Brzozowska, Aleksandra; Azofra, Luis Miguel; Jang, Yoon Kyung; Cavallo, Luigi; Rueping, Magnus

    2017-01-01

    An iron-catalyzed cycloisomerization of allenols to deoxygenated pyranose glycals has been developed. Combined experimental and computational studies show that the iron complex exhibits a dual catalytic role in that the non-innocent cyclopentadienone ligand acts as proton shuttle by initial hydrogen abstraction from the alcohol and by facilitating protonation and deprotonation events in the isomerization and demetalation steps. Molecular orbital analysis provides insight into the unexpected and selective formation of the 3,4-dihydro-2H-pyran.

  18. Computer Based Design and Synthesis of Some Novel Thiazole Derivatives Bearing a Sulfonamide Moiety and Studying Their Potential Synergistic Anticancer Effect With γ-Irradiation

    International Nuclear Information System (INIS)

    Soliman, A.M.M.

    2011-01-01

    In a search for new cytotoxic agents with improved antitumor activity and selectivity, some new thiazole, thiazolo pyrimidine, thiazolo pyrane and thiazolo pyrano pyrimidine derivatives bearing sulfonamide moiety were synthesized. The newly synthesized compounds were evaluated for their antitumor activity alone and in combination with γ-irradiation. These new compounds were docked inside the active site of carbonic anhydrase II to predict their mechanism of action.

  19. Sonogashira–Hagihara reactions of halogenated glycals

    Directory of Open Access Journals (Sweden)

    Dennis C. Koester

    2012-05-01

    Full Text Available Herein, we report on our findings of the Sonogashira–Hagihara reaction with 1-iodinated and 2-brominated glycals using several aromatic and aliphatic alkynes. This Pd-catalyzed cross-coupling reaction presents a facile access to alkynyl C-glycosides and sets the stage for a reductive/oxidative refunctionalization of the enyne moiety to regenerate either C-glycosidic structures or pyran derivatives with a substituent in position 2.

  20. Stable carbon isotope ratios from archaeological charcoal as palaeoenvironmental indicators

    CSIR Research Space (South Africa)

    Hall, G

    2008-01-01

    Full Text Available specific pyrolysis products, mostly furans and pyrans, and released (Steinbeiss et al., 2006). The removal of these compounds is driven by their relative chemical stability and strength of molecular cross bonds. Differences between how... to simulate natural burning conditions and left until completely charred. This produced charcoal under oxidizing (O2-rich) conditions. This process took less than 15 min for the largest disc (60 mm in diameter) and about five minutes for the smallest (30...

  1. 7-Fluoro-4-oxochromene-3-carbaldehyde

    Directory of Open Access Journals (Sweden)

    Mohammad Asad

    2011-04-01

    Full Text Available In the title compound, C10H5FO3, the chromenone ring is essentially planar, with a maximum deviation of 0.039 (1 Å. The dihedral angle between the fluoro-subsituted benzene ring and the pyran ring is 1.92 (4°. In the crystal, molecules are connected via weak intermolecular C—H...O hydrogen bonds, forming supramolecular ribbons along the b axis. These ribbons are stacked down the a axis.

  2. Molecular design of donor-acceptor dyes for efficient dye-sensitized solar cells I: a DFT study.

    Science.gov (United States)

    El-Shishtawy, Reda M; Asiri, Abdullah M; Aziz, Saadullah G; Elroby, Shaaban A K

    2014-06-01

    Dye-sensitized solar cells (DSSCs) have drawn great attention as low cost and high performance alternatives to conventional photovoltaic devices. The molecular design presented in this work is based on the use of pyran type dyes as donor based on frontier molecular orbitals (FMO) and theoretical UV-visible spectra in combination with squaraine type dyes as an acceptor. Density functional theory has been used to investigate several derivatives of pyran type dyes for a better dye design based on optimization of absorption, regeneration, and recombination processes in gas phase. The frontier molecular orbital (FMO) of the HOMO and LUMO energy levels plays an important role in the efficiency of DSSCs. These energies contribute to the generation of exciton, charge transfer, dissociation and exciton recombination. The computations of the geometries and electronic structures for the predicted dyes were performed using the B3LYP/6-31+G** level of theory. The FMO energies (EHOMO, ELUMO) of the studied dyes are calculated and analyzed in the terms of the UV-visible absorption spectra, which have been examined using time-dependent density functional theory (TD-DFT) techniques. This study examined absorption properties of pyran based on theoretical UV-visible absorption spectra, with comparisons between TD-DFT using B3LYP, PBE, and TPSSH functionals with 6-31+G (d) and 6-311++G** basis sets. The results provide a valuable guide for the design of donor-acceptor (D-A) dyes with high molar absorptivity and current conversion in DSSCs. The theoretical results indicated 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran dye (D2-Me) can be effectively used as a donor dye for DSSCs. This dye has a low energy gap by itself and a high energy gap with squaraine acceptor type dye, the design that reduces the recombination and improves the photocurrent generation in solar cell.

  3. Síntesis del 3-p-metoxibenzoil-4-hidroxi-6-p-metoxifenil-2H-piran-2-ona

    Directory of Open Access Journals (Sweden)

    María Soledad Ortiz

    2013-05-01

    Full Text Available During the study of conditions to prepare p-methoxybenzoylacetic acid methyl ester fromp-methoxyacetophenone andmethyl carbonate using sodium hydride in refluxing ethyl ether, the desired product was obtained with 82% yield. Moreover, a slight variation in reaction conditions, such as solvent and temperature, the 3-p-methoxy benzoyl-4-hydroxi-6-p-methoxyphenyl-2H-pyran-2-one was obtained as an unexpected major product.

  4. Experimental and Computational Study of an Unexpected Iron-Catalyzed Carboetherification by Cooperative Metal and Ligand Substrate Interaction and Proton Shuttling

    KAUST Repository

    El-Sepelgy, Osama

    2017-09-26

    An iron-catalyzed cycloisomerization of allenols to deoxygenated pyranose glycals has been developed. Combined experimental and computational studies show that the iron complex exhibits a dual catalytic role in that the non-innocent cyclopentadienone ligand acts as proton shuttle by initial hydrogen abstraction from the alcohol and by facilitating protonation and deprotonation events in the isomerization and demetalation steps. Molecular orbital analysis provides insight into the unexpected and selective formation of the 3,4-dihydro-2H-pyran.

  5. Polyethyleneimine-modified superparamagnetic Fe3O4 nanoparticles: An efficient, reusable and water tolerance nanocatalyst

    International Nuclear Information System (INIS)

    Khoobi, Mehdi; Delshad, Tayebeh Modiri; Vosooghi, Mohsen; Alipour, Masoumeh; Hamadi, Hosein; Alipour, Eskandar; Hamedani, Majid Pirali; Sadat ebrahimi, Seyed Esmaeil; Safaei, Zahra; Foroumadi, Alireza; Shafiee, Abbas

    2015-01-01

    A novel magnetically separable catalyst was prepared based on surface modification of Fe 3 O 4 magnetic nanoparticle (MNPs) with polyethyleneimine (PEI) via covalent bonding. [3-(2,3-Epoxypropoxy)propyl]trimethoxysilane (EPO) was used as cross linker to bond PEI on the surface of MNPs with permanent stability in contrast to PEI coating via electrostatic interactions. The synthesized catalyst was characterized by Fourier transform infrared (FT-IR), thermogravimetric analysis (TGA), X-ray powder diffraction (XRD), transmission electron microscopy (TEM) and vibrating sample magnetometry (VSM). The catalyst show high efficiency for one-pot synthesis of 2-amino-3-cyano-4H-pyran derivatives via multi-component reaction (MCR). This procedure offers the advantages of green reaction media, high yield, short reaction time, easy purification of the products and simple recovery and reuse of the catalyst by simple magnetic decantation without significant loss of catalytic activity. - Graphical abstract: Covalently grafted polyethyleneimine on Fe 3 O 4 magnetic nanoparticles as easily reusable catalyst for the synthesis of various 4H-pyrans. - Highlights: • Polyethyleneimine modified Fe 3 O 4 via covalent bonding as a novel water tolerance catalyst. • The catalyst showed high efficiency for one-pot synthesis of 2-amino-3-cyano-4H-pyrans in water. • Catalysts could be easily recovered and reused for several times without a significant loss in their catalytic activity

  6. Crystal structure of diaphorin methanol monosolvate isolated from Diaphorina citri Kuwayama, the insect vector of citrus greening disease.

    Science.gov (United States)

    Szebenyi, D Marian; Kriksunov, Irina; Howe, Kevin J; Ramsey, John S; Hall, David G; Heck, Michelle L; Krasnoff, Stuart B

    2018-04-01

    The title compound C 22 H 39 NO 9 ·CH 3 OH [systematic name: ( S )- N -(( S )-{(2 S ,4 R ,6 R )-6-[( S )-2,3-di-hydroxy-prop-yl]-4-hy-droxy-5,5-di-methyl-tetra-hydro-2 H -pyran-2-yl}(hy-droxy)meth-yl)-2-hy-droxy-2-[(2 R ,5 R ,6 R )-2-meth-oxy-5,6-dimeth-yl-4-methyl-ene-tetra-hydro-2 H -pyran-2-yl]acetamide methanol monosolvate], was isolated from the Asian citrus psyllid, Diaphorina citri Kuwayama, and crystallizes in the space group P 2 1 . ' Candidatus Profftella armatura' a bacterial endosymbiont of D. citri , biosynthesizes diaphorin, which is a hybrid polyketide-nonribosomal peptide comprising two highly substituted tetra-hydro-pyran rings joined by an N -acyl aminal bridge [Nakabachi et al. (2013 ▸). Curr. Biol. 23 , 1478-1484]. The crystal structure of the title compound establishes the complete relative configuration of diaphorin, which agrees at all nine chiral centers with the structure of the methanol monosolvate of the di- p -bromo-benzoate derivative of pederin, a biogenically related compound whose crystal structure was reported previously [Furusaki et al. (1968 ▸). Tetra-hedron Lett. 9 , 6301-6304]. Thus, the absolute configuration of diaphorin is proposed by analogy to that of pederin.

  7. Solution processable 2-(trityloxy)ethyl and tert-butyl group containing amorphous molecular glasses of pyranylidene derivatives with light-emitting and amplified spontaneous emission properties

    Science.gov (United States)

    Zarins, Elmars; Vembris, Aivars; Misina, Elina; Narels, Martins; Grzibovskis, Raitis; Kokars, Valdis

    2015-11-01

    Small organic molecules with incorporated 4H-pyran-4-ylidene (pyranylidene) fragment as the π-conjugation system which bonds the electron acceptor fragment (A) with electron donor part (D) in the molecule - also well known as derivatives of 4-(dicyano-methylene)-2-methyl-6-[p-(dimethylamino)styryl]-4H-pyran (DCM) laser dye-have attracted considerable attention of scientists as potential new generation materials for organic photonics and molecular electronics due to their low-cost fabrication possibility, flexibility and low-weight. Six glassy derivatives of 4H-pyran-4-ylidene (pyranylidene) with attached bulky 2-(trityloxy)ethyl and tert-butyl groups are described in this report. Almost all of the synthesized compounds form good optical quality transparent amorphous films from volatile organic solvents and could be obtained in good yields up to 75%. Their light emission in solution and thin solid films is in the range of 600-700 nm, they are thermally stable and show glass transition in the range of 108-158 °C. The amplified spontaneous emission threshold values of the neat films of the glassy pyranylidene derivatives vary from 155 to 450 μJ/cm2 and their HOMO and LUMO energy levels are between of those of tris(8-hydroxy quinolinato) aluminum (Alq3). The photoluminescence quantum yields of the glassy compounds are in the range from 1% to about 7.7% and their electroluminescence properties have been investigated. Therefore, glassy pyranylidene derivatives could be a very potential low-cost solution processable materials for Alq3 hosted light-amplification and light-emitting application studies.

  8. Vicinal 1H-1H NMR coupling constants from density functional theory as reliable tools for stereochemical analysis of highly flexible multichiral center molecules.

    Science.gov (United States)

    López-Vallejo, Fabian; Fragoso-Serrano, Mabel; Suárez-Ortiz, Gloria Alejandra; Hernández-Rojas, Adriana C; Cerda-García-Rojas, Carlos M; Pereda-Miranda, Rogelio

    2011-08-05

    A protocol for stereochemical analysis, based on the systematic comparison between theoretical and experimental vicinal (1)H-(1)H NMR coupling constants, was developed and applied to a series of flexible compounds (1-8) derived from the 6-heptenyl-5,6-dihydro-2H-pyran-2-one framework. The method included a broad conformational search, followed by geometry optimization at the DFT B3LYP/DGDZVP level, calculation of the vibrational frequencies, thermochemical parameters, magnetic shielding tensors, and the total NMR spin-spin coupling constants. Three scaling factors, depending on the carbon atom hybridizations, were found for the (1)H-C-C-(1)H vicinal coupling constants: f((sp3)-(sp3)) = 0.910, f((sp3)-(sp2)) = 0.929, and f((sp2)-(sp2))= 0.977. A remarkable correlation between the theoretical (J(pre)) and experimental (1)H-(1)H NMR (J(exp)) coupling constants for spicigerolide (1), a cytotoxic natural product, and some of its synthetic stereoisomers (2-4) demonstrated the predictive value of this approach for the stereochemical assignment of highly flexible compounds containing multiple chiral centers. The stereochemistry of two natural 6-heptenyl-5,6-dihydro-2H-pyran-2-ones (14 and 15) containing diverse functional groups in the heptenyl side chain was also analyzed by application of this combined theoretical and experimental approach, confirming its reliability. Additionally, a geometrical analysis for the conformations of 1-8 revealed that weak hydrogen bonds substantially guide the conformational behavior of the tetraacyloxy-6-heptenyl-2H-pyran-2-ones.

  9. Iodine - catalyzed prins cyclization of aliphatic and aromatic ketones

    International Nuclear Information System (INIS)

    Kishore, K.R.; Reddy, K.; Silva Junior, Luiz F.

    2013-01-01

    Iodine-catalyzed Prins cyclization of homoallylic alcohols and ketones was investigated. Anhydrous conditions and inert atmosphere are not required in this metal-free protocol. The reaction of 2-(3,4-dihydronaphthalene-1-yl)propan-1-ol with six aliphatic symmetric ketones gave the desired products in 67-77% yield. Cyclization was performed with four aliphatic unsymmetric ketones, leading to corresponding pyrans in 66-76% yield. Prins cyclization was also accomplished with four aromatic ketones in 37-66% yield. Finally, Prins cyclization of the monoterpene isopulegol and acetone was successfully achieved. (author)

  10. Phosphine-catalyzed cycloadditions of allenic ketones: new substrates for nucleophilic catalysis.

    Science.gov (United States)

    Wallace, Debra J; Sidda, Rachel L; Reamer, Robert A

    2007-02-02

    A range of phosphine-catalyzed cycloaddition reactions of allenic ketones have been studied, extending the scope of these processes from the more widely used 2,3-butadienoates to allow access to a number of synthetically useful products. Reaction of allenyl methyl ketone 4 with exo-enones afforded spirocyclic compounds in good regioselectivity and promising enantioselectivity via a [2 + 3] cycloaddtion. Aromatic allenyl ketones undergo a phosphine-promoted dimerization to afford functionalized pyrans, leading to a formal [2 + 4] Diels-Alder product, but did not react in the [2 + 3] cycloaddition. The results from other reactions that had found utility with 2,3-butadienoates are also reported.

  11. [Two novel isocoumarins from Erigeron breviscapus].

    Science.gov (United States)

    Li, Jing; Yu, De-Quan

    2013-07-01

    Two novel isocoumarins, erigeronone C (1) and D (2), were isolated from the ethanol extract of the whole plant of Erigeron breviscapus (Vant.) Hand.-Mazz (Compositae). Their structures were respectively elucidated as 8, 9-dihydroxypyrano [3, 2-c] isochromen-4, 6-dione (1) and 4, 7-dihydroxy-3-(3-hydroxy-4-oxo-4H-pyran-2-yl)-1H-isochromen-1-one (2) on the basis of spectral analyses. Both structures of 1 and 2 possess a gamma-pyrone moiety and that is rare in natural products.

  12. (2-Oxo-2H-benzo[h]chromen-4-ylmethyl morpholine-4-carbodithioate

    Directory of Open Access Journals (Sweden)

    Rajni Kant

    2012-04-01

    Full Text Available In the title compound, C19H17NO3S2, the morpholine ring is in a chair conformation. In the coumarin ring system, the dihedral angle between the benzene and pyran rings is 3.9 (1°. In the crystal, weak C—H...O interactions link the molecules into corrugated layers parallel to (102. The crystal packing also exhibits π–π interactions, with distances of 3.644 (1 and 3.677 (1 Å between the centroids of the benzene rings of neighbouring molecules.

  13. Synthesis of 1-[11C]-D,L-homocysteine thiolactone: a potential tracer for myocardial ischemia using PET

    International Nuclear Information System (INIS)

    Hamacher, K.; Hanus, J.

    1989-01-01

    The synthesis of 1-[ 11 C]-D,L-homocysteine thiolactone, a potential tracer for PET imaging of ischemic heart regions, is described. The labelling is achieved by reaction of [ 11 C]carbon dioxide with α-lithiated S-(tetrahydro-pyran-2-yl)3-thiopropylisonitrile. Deprotection of the mercapto group and lactonisation of the resulting thioamino acid is accomplished in an acid catalysed reaction. The radiochemical yield obtained is 10 to 15% and the synthesis time, including the HPLC purification is about 45 min. (author)

  14. Two New Iridoids from Verbena officinalis L.

    Directory of Open Access Journals (Sweden)

    Jicheng Shu

    2014-07-01

    Full Text Available Two new iridoids, 3-(5-(methoxycarbonyl-2-oxo-2H-pyran-3-ylbutanoic acid, named verbeofflin I (1, and 7-hydroxydehydrohastatoside (2, were isolated from the aerial part of Verbena officinalis L, along with three known iridoids, verbenalin (3, 3,4-dihydroverbenalin (4, hastatoside (5 by means of various column chromatography steps. The structures of these compounds were elucidated through analysis of their spectroscopic data obtained using 1D and 2D NMR and MS techniques. Verbeofflin I (1 is the new class of secoiridoid in the family Verbenaceae.

  15. Synthesis of (±)-8-deisopropyladunctin B.

    Science.gov (United States)

    Nomura, Sayo; Arimitsu, Kenji; Yamaguchi, Satoshi; Kosuga, Yuya; Kakimoto, Yuko; Komai, Takanori; Hasegawa, Kazumasa; Nakanishi, Akira; Miyoshi, Tamami; Iwasaki, Hiroki; Ozeki, Minoru; Kawasaki, Ikuo; Kurume, Ai; Ohta, Shunsaku; Yamashita, Masayuki

    2012-01-01

    (±)-8-Deisopropyladunctin B, the deisopropyl form of adunctin B, which was isolated from the leaves of Piper aduncum (Piperaceae) collected in Papua New Guinea, was synthesized in 0.77% overall yield in 17 steps from 5,7-dimethoxycoumarin-3-carboxylate. The key step was our original stereoconvergent skeleton transformation from 1,2,2a,8b-tetrahydro-3H-benzo[b]cyclobuta[d]pyran-3-one to 1,2,4a,9b-tetrahydrodibenzofuran-4-ol with dimethylsulfoxonium methylide.

  16. Soyasaponins resist extrusion cooking and are not degraded during gut passage in Atlantic salmon (Salmo salar L.)

    DEFF Research Database (Denmark)

    Knudsen, Sven David Lausten; Røn, Ø.; Baardsen, G.

    2006-01-01

    The stability of soyasaponins in fish feed formulations was investigated. The level of soyasaponin Ab, Bb, Bc, Ba-2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one (Ba-DDMP), Bb-DDMP, and BcDDMP was quantified in 15 samples of defatted soybean meal, two full fat soybean meals, and two soybean pro....... The present work demonstrates that non-DDMP-conjugated group B soyasaponins resist extrusion cooking and remain intact during gut passage in Atlantic salmon. The latter is contrary to earlier findings in endothermic animals....

  17. Iodine - catalyzed prins cyclization of aliphatic and aromatic ketones

    Energy Technology Data Exchange (ETDEWEB)

    Kishore, K.R.; Reddy, K.; Silva Junior, Luiz F., E-mail: luizfsjr@iq.usp.br [Universidade de Sao Paulo (IQ/USP), SP (Brazil). Inst. de Quimica. Dept. de Quimica Fundamental

    2013-09-15

    Iodine-catalyzed Prins cyclization of homoallylic alcohols and ketones was investigated. Anhydrous conditions and inert atmosphere are not required in this metal-free protocol. The reaction of 2-(3,4-dihydronaphthalene-1-yl)propan-1-ol with six aliphatic symmetric ketones gave the desired products in 67-77% yield. Cyclization was performed with four aliphatic unsymmetric ketones, leading to corresponding pyrans in 66-76% yield. Prins cyclization was also accomplished with four aromatic ketones in 37-66% yield. Finally, Prins cyclization of the monoterpene isopulegol and acetone was successfully achieved. (author)

  18. Structure of products of the condensation of α,β-unsaturated aldehydes with dimedone

    International Nuclear Information System (INIS)

    Yurchenko, O.I.; Pushkareva, K.S.; Zheldubovskaya, G.A.; Komarov, N.V.; Berkova, G.A.

    1987-01-01

    α,β-Acetylenic aldehydes and cinnamaldehyde in reaction with dimedone give the corresponding unsaturated bis(dimedonyl)methanes. In the case of acrolein and crotonaldehyde intramolecular cyclization occurs with the participation of hydroxyl of the dimedone fragment and the double bond with the formation of pyran systems. The PMR spectra were determined on Tesla BS-487C (80 MHz) and Tesla BS-467C (60 MHz) spectrometers in chloroform-d, pyridine-d 5 , and trifluoroacetic acid solutions. Internal standards HMDS and methylene chloride

  19. Influence of dehydrated nanotubed titanic acid on charge transport and luminescent properties of polymer light-emitting diodes with fluorescent dye

    Science.gov (United States)

    Qian, Lei; Bera, Debasis; Jin, Zhen-Sheng; Du, Zu-Liang; Xu, Zheng; Teng, Feng; Liu, Wei

    2007-09-01

    In this paper, we discuss the influence of dehydrated nanotubed titanic acid (DNTA) on charge transport and luminescent properties of polymer light-emitting diodes (PLEDs) doped with fluorescent dye. Photoluminescence results confirm the efficient energy transfer from PVK to 4-(dicyanom-ethylene)-2- t-butyl-6-(1,1,7,7-tetramethyljulolidyl-9-enyl)-4H-pyran (DCJTB) and tris-(8-hydroxtquinoline) aluminum (Alq 3) in a DNTA-doped device. The device showed lower turn-on voltages and higher charge current by doping with DNTA, which also caused a shift in the exciton's recombination region.

  20. 2-Acetylamino-1,3,4,6-tetra-O-(trimethylsilyl-2-deoxy-α-d-glucopyranose

    Directory of Open Access Journals (Sweden)

    Zhao-Dong Cheng

    2013-06-01

    Full Text Available The title compound, C20H47NO6Si4, was synthesized by per-O-trimethylsilylation of N-acetyl-d-glucosamine using chlorotrimethylsilane in the presence of hexamethyldisiloxane. The trimethylsilyl group and acetamido group are located on the same side of the pyran ring, showing an α-configuration glycoside. One of the trimethylsilyl groups is disordered over two orientations, with site-occupancy factors of 0.625 (9 and 0.375 (9. In the crystal, N—H...O hydrogen bonds link the molecules into supramolecular chains along the a-axis direction.

  1. Silver triflate/p-TSA co-catalysed synthesis of 3-substituted isocoumarins from 2-alkynylbenzoates.

    Science.gov (United States)

    Gianni, Jonathan; Pirovano, Valentina; Abbiati, Giorgio

    2018-05-02

    In this paper, we describe the silver triflate/p-toluenesulfonic acid co-catalysed synthesis of seventeen isocoumarins and two thieno[2,3-c]pyran-7-ones starting from 2-alkynylbenzoates and 3-alkynylthiophene-2-carboxylates, respectively. The reaction proceeds with absolute regioselectivity under mild reaction conditions and low catalyst loading, to afford the desired products in good to excellent yields. A conceivable reaction mechanism is proposed and supported by isotope-exchange tests, 1H NMR studies and ad hoc experiments.

  2. Binary heterocyclic systems containing the ethylideneamino linkage: synthesis of some new heterocyclic compounds bearing the naphtho-[2,1-b]furan moiety

    Directory of Open Access Journals (Sweden)

    A. H. BEDAIR

    2006-05-01

    Full Text Available Ethylidene hydrazine (4a,b and thiazolidin-4-one (5 derivatives were synthesized by the reaction of ethylidenethiosemicarbazide derivative (3a with a-haloketone/ethyl bromoacetate, respectively. Hetrocyclization of ethylideneacetohydrazide derivative (7 with o-phenolic aldehydes gave the corresponding coumarin derivatives (8,9. The interaction of 7 with acetylacetone afforded the corresponding pyridine derivative (10. Treatment of the arylidene derivative 11b with malononitrile afforded the corresponding pyran derivative (12. The new products 3-12 were subjected to IR, 1H NMR and mass spectra studies.

  3. Reactions of carbonyl compounds with α,β-unsaturated nitriles as a convenient pathway to carbo- and heterocycles

    International Nuclear Information System (INIS)

    Sharanin, Yu A; Goncharenko, M P; Litvinov, Victor P

    1998-01-01

    Published data on the methods for synthesis of carbo- and heterocyclic compounds based on reactions of α,β-unsaturated nitriles with carbonyl compounds and activated phenols are surveyed. It is demonstrated that all these reactions occur via nucleophilic addition of the carbanion generated from a carbonyl compound to the double bond of an unsaturated nitrile (the Michael reaction). The main routes of transformation of the adducts into carbo- and heterocyclic compounds are considered. The methods for regioselective preparation of fused 4H-pyrans or 1,4-dihydropyridines by varying conditions of cyclisation of Michael adducts are discussed. The bibliography includes 249 references.

  4. Synthesis of Novel Heterocyclic Compounds Incorporate 4,5,6,7-Tetrahydrobenzo[b]thiophene Together with Their Cytotoxic Evaluations.

    Science.gov (United States)

    Abdallah, Amira Elsayed Mahmoud; Mohareb, Rafat Milad; Khalil, Eid Metwally; Elshamy, Menna Alla Mohamed Abd Elaleem

    2017-01-01

    The 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene was the key starting compound used to synthesize new thiazole, pyrimidine, pyran, pyridine and thiazine derivatives. The cytotoxicity of the synthesized compounds was studied towards the three cancer cell lines namely MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and SF-268 (central nervous system (CNS) cancer) in addition to the normal cell line (WI-38) using doxorubicin as the reference drug. The study showed that compounds 5, 9a, 15b, 17c, 18 and 21b were the most potent compounds.

  5. Synthesis and Antibacterial Evaluation of Novel Heterocyclic Compounds Containing a Sulfonamido Moiety

    Directory of Open Access Journals (Sweden)

    Eman A. El-Bordany

    2013-01-01

    Full Text Available Aiming for the synthesis of new heterocyclic compounds containing a sulfonamido moiety suitable for use as antibacterial agents, the precursor ethyl {[4-N-(4,6-dimethylpyrimidin-2-ylsulfamoyl]phenylazo}cyanoacetate was reacted with a variety of active methylene compounds producing pyran, pyridine and pyridazine derivatives. Also, the reactivity of the precursor hydrazone towards hydrazine derivatives to give pyrazole and oxazole derivatives was studied. On the other hand, treatment of the same precursor with urea, thiourea and/or guanidine hydrochloride furnished pyrimidine and thiazine derivatives, respectively. The newly synthesized compounds were tested for antibacterial activity, whereby eight compounds were found to have high activities.

  6. Thermometric Study of Inhibition of Aluminium Corrosion in Hydrochloric Acid Solution

    OpenAIRE

    Al Gaber, A.S. [امينة سلطان الجابر; Seliman, S. A.; Mourad, M.

    1997-01-01

    The use of 6- amino - 4- (4-phenyl)-l,4- dihydro -3- methylpyrano [2,3- c] pyrazole -5- carbonitrile and some related compounds as corrosion inhibitors for aluminium in 2 M HCl solution was studied by the thermometric method. The results indicate that the additives reduce the corrosion rate via weak adsorption through the cationic oxygen of the pyran ring. They act as mixed inhibitors and their adsorption was found to obey Frumkin's isotherm. The inhibition efficiency of the additives is rela...

  7. The [2 + 2] Cycloaddition-Retroelectrocyclization and [4 + 2] Hetero-Diels-Alder Reactions of 2-(Dicyanomethylene)indan-1,3-dione with Electron-Rich Alkynes: Influence of Lewis Acids on Reactivity.

    Science.gov (United States)

    Donckele, Etienne J; Finke, Aaron D; Ruhlmann, Laurent; Boudon, Corinne; Trapp, Nils; Diederich, François

    2015-07-17

    The reaction of electrophilic 2-(dicyanomethylene)indan-1,3-dione (DCID) with substituted, electron-rich alkynes provides two classes of push-pull chromophores with interesting optoelectronic properties. The formal [2 + 2] cycloaddition-retroelectrocyclization reaction at the exocyclic double bond of DCID gives cyanobuta-1,3-dienes, and the formal [4 + 2] hetero-Diels-Alder (HDA) reaction at an enone moiety of DCID generates fused 4H-pyran heterocycles. Both products can be obtained in good yield and excellent selectivity by carefully tuning the reaction conditions; in particular, the use of Lewis acids dramatically enhances formation of the HDA adduct.

  8. Studies toward the asymmetric synthesis of the right part of the mycalamides.

    Science.gov (United States)

    Zhong, H Marlon; Sohn, Jeong-Hun; Rawal, Viresh H

    2007-01-19

    Described herein is the asymmetric synthesis of a functionalized, trioxadecalin unit that comprises the right-hand part of the mycalamides and related natural products. The synthetic route involves a 16-step sequence that accomplishes the formation of two heterocyclic rings and the generation of five stereocenters. The synthesis commenced with a C2-symmetric starting material, diethyl D-tartrate, and took advantage of a relay of diastereoselective reactions to extend this four-carbon chain and introduce new chiral centers. Subsequent electrophile-mediated cyclization afforded the desired pyran ring, which was then transformed into the desired, functionalized trioxadecalin skeleton.

  9. Encapsulation of dye molecules into mesoporous polymer resin and mesoporous polymer-silica films by an evaporation-induced self-assembly method

    Energy Technology Data Exchange (ETDEWEB)

    Chi Yue; Li Nan; Tu Jinchun; Zhang Yujie [School of Material Science and Engineering, Key Laboratory of Automobile Materials of Ministry of Education, Jilin University, Changchun 130012 (China); Li Xiaotian, E-mail: xiaotianli@jlu.edu.c [School of Material Science and Engineering, Key Laboratory of Automobile Materials of Ministry of Education, Jilin University, Changchun 130012 (China); Shao Changlu, E-mail: clshao@nenu.edu.c [Center for Advanced Optoelectronic Functional Materials Research, Northeast Normal University, Changchun 130024 (China)

    2010-03-15

    Polymer resin and polymer-silica films with highly ordered mesostructure have been used as host materials to encapsulate DCM (4-(dicyanomethylene) -2-methyl-6-(4-dimethylaminostyryl)-4h-pyran), a kind of fluorescent dye, through evaporation-induced self-assembly method (EISA). After encapsulation, the composites show significant blue-shift in photoluminescence (PL) spectra. Particularly, by changing the excitation wavelength, the samples show different emission bands. These phenomena are related to the mesostructure and the positions of DCM molecules in the host.

  10. Pd(II)-Catalyzed Hydroxyl-Directed C–H Olefination Enabled by Mono-Protected Amino Acid Ligands

    Science.gov (United States)

    Lu, Yi; Wang, Dong-Hui; Engle, Keary M.

    2010-01-01

    A novel Pd(II)-catalyzed ortho-C–H olefination protocol has been developed using spatially remote, unprotected tertiary, secondary, and primary alcohols as the directing groups. Mono-N-protected amino acid ligands were found to promote the reaction, and an array of olefin coupling partners could be used. When electron-deficient alkenes were used, the resulting olefinated intermediates underwent subsequent Pd(II)-catalyzed oxidative intramolecular cyclization to give the corresponding pyran products, which could be converted into ortho-alkylated alcohols under hydrogenolysis conditions. The mechanistic details of the oxidative cyclization step are discussed and situated in the context of the overall catalytic cycle. PMID:20359184

  11. Enantioselctive Syntheses of Sulfur Analogues of Flavan-3-Ols

    Directory of Open Access Journals (Sweden)

    Richard Lombardy

    2010-08-01

    Full Text Available The first enantioselective syntheses of sulfur flavan-3-ol analogues 1–8 have been accomplished, whereby the oxygen atom of the pyran ring has been replaced by a sulfur atom. The key steps were: (a Pd(0 catalyzed introduction of –S t-butyl group, (b Sharpless enantioselective dihydroxylation of the alkene, (c acid catalyzed ring closure to produce the thiopyran ring, and (d removal of benzyl groups using N,N-dimethylaniline and AlCl3. The compounds were isolated in high chemical and optical purity.

  12. The fragment ion C13H9O2 m/z 197 in the mass spectra of 2-(2'-R-phenyl)benzoic acids

    International Nuclear Information System (INIS)

    Gills, R.G.; Porter, Q.N.

    1990-01-01

    In the electron impact mass spectrum of 2-( ' -R-phenyl)benzoic acids where R = H, NO 2 , OCH 3 , COOH, or Br, and abundant fragment ion m/z 197 is formed by an ipso substitution in which R is expelled as a radical. The structure of the ion m/z 197 has been shown by collision-activated dissociation to be identical with that of the protonated molecule formed by methane chemical ionization of 6H-dibenzo[b,d]pyran-6-one. 11 refs., 1 fig., ills

  13. Generation of Maillard compounds from inulin during the thermal processing of Agave tequilana Weber Var. azul.

    Science.gov (United States)

    Mancilla-Margalli, Norma A; López, Mercedes G

    2002-02-13

    During the cooking process of Agave tequilana Weber var. azul to produce tequila, besides the hydrolysis of inulin to generate fermentable sugars, many volatiles, mainly Maillard compounds, are produced, most of which may have a significant impact on the overall flavor of tequila. Exudates (agave juice) from a tequila company were collected periodically, and color, Brix, fructose concentration, and reducing sugars were determined as inulin breakdown took place. Maillard compounds were obtained by extraction with CH(2)Cl(2), and the extracts were analyzed by GC-MS. Increments in color, Brix, and reducing sugars were observed as a function of time, but a decrease in fructose concentration was found. Many Maillard compounds were identified in the exudates, including furans, pyrans, aldehydes, and nitrogen and sulfur compounds. The most abundant Maillard compounds were methyl-2-furoate, 2,3-dihydroxy-3,5-dihydro-6-methyl-4(H)-pyran-4-one, and 5-(hydroxymethyl)furfural. In addition, a series of short- and long-chain fatty acids was also found. A large number of the volatiles in A. tequilana Weber var. azul were also detected in tequila extracts, and most of these have been reported as a powerful odorants, responsible for the unique tequila flavor.

  14. Suppression of developmental anomalies by maternal macrophages in mice

    International Nuclear Information System (INIS)

    Nomura, T.; Hata, S.; Kusafuka, T.

    1990-01-01

    We tested whether nonspecific tumoricidal immune cells can suppress congenital malformations by killing precursor cells destined to cause such defects. Pretreatment of pregnant ICR mice with synthetic (Pyran copolymer) and biological (Bacillus Calmette-Guerin) agents significantly suppressed radiation- and chemical-induced congenital malformations (cleft palate, digit anomalies, tail anomalies, etc.). Such suppressive effects were associated with the activation of maternal macrophages by these agents, but were lost either after the disruption of activated macrophages by supersonic waves or by inhibition of their lysosomal enzyme activity with trypan blue. These results indicate that a live activated macrophage with active lysosomal enzymes can be an effector cell to suppress maldevelopment. A similar reduction by activated macrophages was observed in strain CL/Fr, which has a high spontaneous frequency of cleft lips and palates. Furthermore, Pyran-activated maternal macrophages could pass through the placenta, and enhanced urethane-induced cell killing (but not somatic mutation) in the embryo. It is likely that a maternal immunosurveillance system eliminating preteratogenic cells allows for the replacement with normal totipotent blast cells during the pregnancy to protect abnormal development

  15. Electrochemical properties of manganese and rhenium complexes with organic redox ligands

    Energy Technology Data Exchange (ETDEWEB)

    Bumberg, A.A.; Milaev, A.G.; Okhlobystin, O.Yu.

    1983-03-01

    Pyrilium salts, 4H-pyrans and phenols that contain sigma-bound groups M(CO)/sub 3/ (M=Mn, Re) are investigated using the methods of classic and commutated polarography, disc rotating electrode with a ring and cyclic voltamperometry. The first single electron stage of electrochemical reduction of pyrilium cations containing sigma-bound substitutuents ..pi..=C/sub 5/H/sub 4/M(CO/sub 3/) (M=Mn, Re) takes place without any rupture of metal-carbon bonds and brings about rather stable vacant, metal organic radicals. Electrochemical dehydration of appropriate 4H-pyrans takes place through a stage of formation of these vacant radicals and complexes with the formation of metal organic pyrilium cations. Electrochemical oxidation of spatially hindrance phenols containing in 4-th position ..pi..-C/sub 5/H/sub 4/Re(CO/sub 3/) and C/sub 5/H/sub 4/Mn(CO)/sub 2/P(Ph)/sub 3/ substitutes takes place with the formation of appropriate cation radicals as intermediates and brings about vacant phenoxyls that contain charged organometallic group.

  16. Solvent-dependent fluorescence enhancement and piezochromism of a carbazole-substituted naphthopyran

    Energy Technology Data Exchange (ETDEWEB)

    Liu, Lihui; Wang, Aixia [Faculty of Chemistry, Northeast Normal University, Changchun 130024 (China); Wang, Guang, E-mail: wangg923@nenu.edu.cn [Faculty of Chemistry, Northeast Normal University, Changchun 130024 (China); Munyentwari, Alexis [Faculty of Chemistry, Northeast Normal University, Changchun 130024 (China); Zhou, Yihan, E-mail: yhzhou@ciac.ac.cn [National Analytical Research Center of Electrochemistry and Spectroscopy, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022 (China)

    2015-09-15

    A novel carbazole-substituted naphthopyran, 3,3-bis-(4-carbazolylphenyl)-[3H]-naphtho[2,1-b]pyran (CzNP) was designed and synthesized. The new compound exhibited normal photochromism in dichloromethane solution and the UV irradiation did not influence its fluorescence. On the contrary, the fluorescence of CzNP in N,N-dimethylformamide (DMF) was intensively enhanced to 29 times after 60 min of the UV irradiation and this enhanced fluorescence can be quenched by addition of triethylamine (TEA). The study of enhanced extent of fluorescence of CzNP in solvents with different polarities and in mixed solvents demonstrated that the enhanced fluorescence is dependent on the polarity of solvents. The larger the polarity of solvent was, the stronger was the fluorescence of CzNP. CzNP also exhibited piezochromic performance and the pressure led to the cleavage of the C–O bond of pyran ring. - Highlights: • A carbazole-substituted photochromic naphthopyran was designed and synthesized. • The fluorescence was enhanced under the existence of DMF and UV irradiation. • The polarity of solvent was the dominating factor to affect the fluorescence. • The new compound also displayed piezochromic performance.

  17. Antimicrobial activity of Paepalanthus planifolius and its major components against selected human pathogens

    International Nuclear Information System (INIS)

    Amorim, Marcelo R. de; Hilário, Felipe; Bauab, Tais M.; Santos, Lourdes C. dos; Sano, Paulo T.

    2018-01-01

    The chemical investigation of ethyl acetate extract from Paepalanthus planifolius capitula resulted in the identification of 1H-naphtho[2,3-c]pyran-1-one,9-[(6-O-β-D-glucopyranosyl- β-D-glucopyranosyl)oxy]-3,4-dihydro-10-hydroxy-7-methoxy-3-methyl, semi-vioxanthin 9-O-β-D-glucopyranoside, toralactone-9-O-β-D-glucopyranoside, paepalantine9-O-β-D-glucopyranoside, semi-vioxanthin, 1 H-naphtho[2,3-c]pyran-1-one,3,4-dihydro-9,10-dihydroxy-5,7-dimethoxy- 3-methyl, vioxanthin and paepalantine dimer, and also the isolation and identification of a new naphthopyranone dimer named planifoliusin A. The chemical structures of two compounds were elucidated by performing spectroscopic 1D and 2D nuclear magnetic resonance (NMR) experiments and spectrometric HRMS (high-resolution mass spectrometry) analysis. Other six naphthopyranone dimers were proposed by MS fragmentation patterns. The minimum inhibitory concentration (MIC) values for vioxanthin (7.8 μg mL -1 ), planifoliusin A (15.6 μg mL -1 ) and the ethyl acetate extract (31.2 μg mL -1 ) showed antimicrobial activity against Staphylococcus aureus (ATCC 25923). (author)

  18. Screen-Printed Photochromic Textiles through New Inks Based on SiO2@naphthopyran Nanoparticles.

    Science.gov (United States)

    Pinto, Tânia V; Costa, Paula; Sousa, Céu M; Sousa, Carlos A D; Pereira, Clara; Silva, Carla J S M; Pereira, Manuel Fernando R; Coelho, Paulo J; Freire, Cristina

    2016-10-26

    Photochromic silica nanoparticles (SiO 2 @NPT), fabricated through the covalent immobilization of silylated naphthopyrans (NPTs) based on 2H-naphtho[1,2-b]pyran (S1, S2) and 3H-naphtho[2,1-b]pyran (S3, S4) or through the direct adsorption of the parent naphthopyrans (1, 3) onto silica nanoparticles (SiO 2 NPs), were successfully incorporated onto cotton fabrics by a screen-printing process. Two aqueous acrylic- (AC-) and polyurethane- (PU-) based inks were used as dispersing media. All textiles exhibited reversible photochromism under UV and solar irradiation, developing fast responses and intense coloration. The fabrics coated with SiO 2 @S1 and SiO 2 @S2 showed rapid color changes and high contrasts (ΔE* ab = 39-52), despite presenting slower bleaching kinetics (2-3 h to fade to the original color), whereas the textiles coated with SiO 2 @S3 and SiO 2 @S4 exhibited excellent engagement between coloration and decoloration rates (coloration and fading times of 1 and 2 min, respectively; ΔE* ab = 27-53). The PU-based fabrics showed excellent results during the washing fastness tests, whereas the AC-based textiles evidenced good results only when a protective transfer film was applied over the printed design.

  19. Design, Synthesis, Structural and Spectroscopic Studies of Push-Pull Two-Photon Absorbing Chromophores with Acceptor Groups of Varying Strength

    Science.gov (United States)

    Morales, Alma R.; Frazer, Andrew; Woodward, Adam W.; Ahn-White, Hyo-Yang; Fonari, Alexandr; Tongwa, Paul; Timofeeva, Tatiana; Belfield, Kevin D.

    2013-01-01

    A new series of unsymmetrical diphenylaminofluorene-based chromophores with various strong π-electron acceptors were synthesized and fully characterized. The systematic alteration of the structural design facilitated the investigation of effects such as molecular symmetry and strength of electron-donating and/or withdrawing termini have on optical nonlinearity. In order to determine the electronic and geometrical properties of the novel compounds, a thorough investigation was carried out by a combination of linear and nonlinear spectroscopic techniques, single crystal X-ray diffraction, and quantum chemical calculations. Finally, on the basis of two-photon absorption (2PA) cross sections, the general trend for π -electron accepting ability, i.e., ability to accept charge transfer from diphenylamine was: 2-pyran-4-ylidene malononitrile (pyranone) > dicyanovinyl > bis(dicyanomethylidene)indane > 1-(thiophen-2-yl)propenone > dicyanoethylenyl > 3-(thiophen-2-yl)propenone. An analog with the 2-pyran-4-ylidene malononitrile acceptor group exhibited a nearly three-fold enhancement of the 2PA< δ (1650 GM at 840 nm), relative to other members of the series. PMID:23305555

  20. Comparative evaluation of two Trichoderma harzianum strains for major secondary metabolite production and antifungal activity.

    Science.gov (United States)

    Ahluwalia, Vivek; Kumar, Jitendra; Rana, Virendra S; Sati, Om P; Walia, S

    2015-01-01

    This investigation was undertaken to identify the major secondary metabolite, produced by two Trichoderma harzianum strains (T-4 and T-5) with their antifungal activity against phytopathogenic fungi using poison food technique. The ethyl acetate extract was subjected to column chromatography using n-hexane, ethyl acetate and methanol gradually. Chromatographic separation of ethyl acetate extract of T. harzianum (T-4) resulted in the isolation and identification of palmitic acid (1), 1,8-dihydroxy-3-methylanthraquinone (2), 6-pentyl-2H-pyran-2-one (3), 2(5H)-furanone (4), stigmasterol (5) and β-sitosterol (6), while T. harzianum (T-5) gave palmitic acid (1), 1-hydroxy-3-methylanthraquinone (7), δ-decanolactone (8), 6-pentyl-2H-pyran-2-one (3), ergosterol (9), harzianopyridone (10) and 6-methyl-1,3,8-trihydroxyanthraquinone (11) as major metabolites. Among compounds screened for antifungal activity, compound 10 was found to be most active (EC50 35.9-50.2 μg mL(-1)). In conclusion, the present investigation provided significant information about antifungal activity and compounds isolated from two different strains of T. harzianum obtained from two different Himalayan locations.

  1. Dihydronepetalactones deter feeding activity by mosquitoes, stable flies, and deer ticks.

    Science.gov (United States)

    Feaster, John E; Scialdone, Mark A; Todd, Robin G; Gonzalez, Yamaira I; Foster, Joseph P; Hallahan, David L

    2009-07-01

    The essential oil of catmint, Nepeta cataria L., contains nepetalactones, that, on hydrogenation, yield the corresponding dihydronepetalactone (DHN) diastereomers. The DHN diastereomer (4R,4aR,7S,7aS)-4,7-dimethylhexahydrocyclopenta[c]pyran-1(3H)-one, DHN 1) was evaluated as mosquito repellent, as was the mixture of diastereomers {mostly (4S,4aR,7S,7aR)-4,7-dimethylhexahydrocyclopenta[c]pyran-1(3H)-one, DHN 2} present after hydrogenation of catmint oil itself. The repellency of these materials to Aedes aegypti L. and Anopheles albimanus Wiedemann mosquitoes was tested in vitro and found to be comparable to that obtained with the well-known insect repellent active ingredient N,N-diethyl-3-methylbenzamide (DEET). DHN 1 and DHN 2 also repelled the stable fly, Stomoxys calcitrans L., in this study. DHN 1, DHN 2, and p-menthane-3,8-diol (PMD), another natural monoterpenoid repellent, gave comparable levels of repellency against An. albimanus and S. calcitrans. Laboratory testing of DHN 1 and DHN 2 using human subjects with An. albimanus mosquitoes was carried out. Both DHN 1 and DHN 2 at 10% (wt:vol) conferred complete protection from bites for significant periods of time (3.5 and 5 h, respectively), with DHN2 conferring protection statistically equivalent to DEET. The DHN 1 and DHN 2 diastereomers were also efficaceous against black-legged tick (Ixodes scapularis Say) nymphs.

  2. Identification of New Lactone Derivatives Isolated from Trichoderma sp., An Endophytic Fungus of Brotowali (Tinaspora crispa

    Directory of Open Access Journals (Sweden)

    ELFITA

    2014-03-01

    Full Text Available Endophytic fungi is a rich source of novel organic compounds with interesting biological activities and a high level of structural diversity. As a part of our systematic search for new bioactive lead structures and specific profiles from endophytic fungi, an endophytic fungus was isolated from roots of brotowali (Tinaspora crispa, an important medicinal plant. Colonial morphological trait and microscopic observation revealed that the endophytic fungus was Trichoderma sp. The pure fungal strain was cultivated on 7 L Potatos Dextose Broth (PDB medium under room temperature (no shaking for 8 weeks. The ethyl acetate were added to cultur medium and left overnight to stop cell growth. The culture filtrates were collected and extracted with EtOAc and then taken to evaporation. Two new lactone derivatives, 5-hydroxy-4-hydroxymethyl-2H-pyran-2-one (1 and (5-hydroxy-2-oxo-2H pyran-4-yl methyl acetate (2 were obtained from the EtOAc extracts of Trichoderma sp. Their structures were determined on the basic of spectroscopic methods including UV, IR, 1H-NMR, 13C-NMR, HMQC, and HMBC.

  3. Antimicrobial activity of Paepalanthus planifolius and its major components against selected human pathogens

    Energy Technology Data Exchange (ETDEWEB)

    Amorim, Marcelo R. de; Hilário, Felipe; Bauab, Tais M.; Santos, Lourdes C. dos [Universidade Estadual Paulista Julio de Mesquita Filho (UNESP), Araraquara, SP (Brazil); Sano, Paulo T., E-mail: loursant@gmail.com [Universidade de São Paulo (USP), São Paulo, SP (Brazil)

    2018-05-01

    The chemical investigation of ethyl acetate extract from Paepalanthus planifolius capitula resulted in the identification of 1H-naphtho[2,3-c]pyran-1-one,9-[(6-O-β-D-glucopyranosyl- β-D-glucopyranosyl)oxy]-3,4-dihydro-10-hydroxy-7-methoxy-3-methyl, semi-vioxanthin 9-O-β-D-glucopyranoside, toralactone-9-O-β-D-glucopyranoside, paepalantine9-O-β-D-glucopyranoside, semi-vioxanthin, {sup 1}H-naphtho[2,3-c]pyran-1-one,3,4-dihydro-9,10-dihydroxy-5,7-dimethoxy- 3-methyl, vioxanthin and paepalantine dimer, and also the isolation and identification of a new naphthopyranone dimer named planifoliusin A. The chemical structures of two compounds were elucidated by performing spectroscopic 1D and 2D nuclear magnetic resonance (NMR) experiments and spectrometric HRMS (high-resolution mass spectrometry) analysis. Other six naphthopyranone dimers were proposed by MS fragmentation patterns. The minimum inhibitory concentration (MIC) values for vioxanthin (7.8 μg mL{sup -1}), planifoliusin A (15.6 μg mL{sup -1}) and the ethyl acetate extract (31.2 μg mL{sup -1}) showed antimicrobial activity against Staphylococcus aureus (ATCC 25923). (author)

  4. Crosslinked polyimide electro-optic materials

    Energy Technology Data Exchange (ETDEWEB)

    Kowalczyk, T.C.; Kosc, T.Z.; Singer, K.D. [Case Western Reserve University, Department of Physics, Cleveland, Ohio 44106-7079 (United States); Beuhler, A.J.; Wargowski, D.A. [Amoco Research Center, Amoco Chemical Co., Naperville, Illinois 60566 (United States); Cahill, P.A.; Seager, C.H.; Meinhardt, M.B. [Sandia National Laboratories, Division 1811, Albuquerque, New Mexico 87185-1407 (United States); Ermer, S. [Lockheed Research and Development Division, Palo Alto, California 94304 (United States)

    1995-11-15

    We report studies of the optical and electro-optic properties of guest--host polymeric nonlinear optical materials based on aromatic, fluorinated, fully imidized, organic soluble, thermally, and photochemically crosslinkable, guest--host polyimides. We have introduced temperature stable nonlinear optical chromophores into these polyimides and studied optical losses, electric field poling, electro-optic properties, and orientational stability. We measured electro-optic coefficients of 5.5 and 12.0 pm/V for ((2,6-Bis(2-(3-(9-(ethyl)carbazolyl))ethenyl)4H-pyran-4-ylidene)propanedinitrile) (4-(Dicyanomethylene)-2-methyl-6-(p -dimethylaminostyryl)-4H-pyran) DCM-doped guest--host systems at 800 nm using a poling field of 1.3 MV/cm. Poling induced nonlinearities in single-layer films were in agreement with the oriented gas model, but were lower in three-layer films due to voltage division across the layers. {copyright} {ital 1995} {ital American} {ital Institute} {ital of} {ital Physics}.

  5. Crystal structure of diaphorin methanol monosolvate isolated from Diaphorina citri Kuwayama, the insect vector of citrus greening disease

    Directory of Open Access Journals (Sweden)

    D. Marian Szebenyi

    2018-04-01

    Full Text Available The title compound C22H39NO9·CH3OH [systematic name: (S-N-((S-{(2S,4R,6R-6-[(S-2,3-dihydroxypropyl]-4-hydroxy-5,5-dimethyltetrahydro-2H-pyran-2-yl}(hydroxymethyl-2-hydroxy-2-[(2R,5R,6R-2-methoxy-5,6-dimethyl-4-methylenetetrahydro-2H-pyran-2-yl]acetamide methanol monosolvate], was isolated from the Asian citrus psyllid, Diaphorina citri Kuwayama, and crystallizes in the space group P21. `Candidatus Profftella armatura' a bacterial endosymbiont of D. citri, biosynthesizes diaphorin, which is a hybrid polyketide–nonribosomal peptide comprising two highly substituted tetrahydropyran rings joined by an N-acyl aminal bridge [Nakabachi et al. (2013. Curr. Biol. 23, 1478–1484]. The crystal structure of the title compound establishes the complete relative configuration of diaphorin, which agrees at all nine chiral centers with the structure of the methanol monosolvate of the di-p-bromobenzoate derivative of pederin, a biogenically related compound whose crystal structure was reported previously [Furusaki et al. (1968. Tetrahedron Lett. 9, 6301–6304]. Thus, the absolute configuration of diaphorin is proposed by analogy to that of pederin.

  6. O-heterocyclic derivatives with antibacterial properties from marine bacterium Bacillus subtilis associated with seaweed, Sargassum myriocystum.

    Science.gov (United States)

    Chakraborty, Kajal; Thilakan, Bini; Chakraborty, Rekha Devi; Raola, Vamshi Krishna; Joy, Minju

    2017-01-01

    The brown seaweed, Sargassum myriocystum associated with heterotrophic bacterium, Bacillus subtilis MTCC 10407 (JF834075) exhibited broad-spectra of potent antibacterial activities against pathogenic bacteria Aeromonas hydrophila, Vibrio vulnificus, and Vibrio parahaemolyticus. B. subtilis MTCC 10407 was found to be positive for polyketide synthetase (pks) gene, and therefore, was considered to characterize secondary metabolites bearing polyketide backbone. Using bioassay-guided fractionation, two new antibacterial O-heterocyclic compounds belonging to pyranyl benzoate analogs of polyketide origin, with activity against pathogenic bacteria, have been isolated from the ethyl acetate extract of B. subtilis MTCC 10407. In the present study, the secondary metabolites of B. subtilis MTCC 10407 with potent antibacterial action against bacterial pathogens was recognized to represent the platform of pks-1 gene-encoded products. Two homologous compounds 3 (3-(methoxycarbonyl)-4-(5-(2-ethylbutyl)-5,6-dihydro-3-methyl-2H-pyran-2-yl)-butyl benzoate) and 4 [2-(8-butyl-3-ethyl-3,4,4a,5,6,8a-hexahydro-2H-chromen-6-yl)-ethyl benzoate] also have been isolated from the ethyl acetate extract of host seaweed S. myriocystum. The two compounds isolated from ethyl acetate extract of S. myriocystum with lesser antibacterial properties shared similar structures with the compounds purified from B. subtilis that suggested the ecological and metabolic relationship between these compounds in seaweed-bacterial relationship. Tetrahydropyran-2-one moiety of the tetrahydropyrano-[3,2b]-pyran-2(3H)-one system of 1 might be cleaved by the metabolic pool of seaweeds to afford methyl 3-(dihydro-3-methyl-2H-pyranyl)-propanoate moiety of 3, which was found to have no significant antibacterial activity. It is therefore imperative that the presence of dihydro-methyl-2H-pyran-2-yl propanoate system is essentially required to impart the greater activity. The direct involvement of polarisability (Pl) with

  7. Transition metal complexes with oxygen donor ligands: a synthesis, spectral, thermal and antimicrobial study

    Directory of Open Access Journals (Sweden)

    VAIBHAV N. PATANGE

    2008-10-01

    Full Text Available Transition metal complexes of chalcones derived from the conden¬sation of 3-acetyl-6-methyl-2H-pyran-2,4(3H-dione (dehydroacetic acid and p-methoxybenzaldehyde (HL1 or p-nitrobenzaldehyde (HL2 were synthesized and characterized by elemental analysis, conductometry, thermal analysis, magnetic measurements, IR, 1H-NMR, UV–Vis spectroscopy and a microbial study. From the analytical and thermal data, the stoichiometry of the complexes was found to be 1:2 (metal:ligand. The molar conductance data revealed that all the metal chelates were non-electrolytes. The thermal stability of the complexes was studied by thermogravimetry and the decomposition schemes of the complexes are given. The ligands and their metal complexes were screened for antibacterial activity against Staphylococcus aureus and Escherichia coli, and fungicidal activity against Aspergillus flavus, Curvularia lunata and Penicillium notatum.

  8. A green approach to the production of 2-pyridone derivatives promoted by infrared irradiation

    Energy Technology Data Exchange (ETDEWEB)

    Hernandez, F.; De la Cruz, F.; Lopez, J.; Pena, E.; Vazquez, M. A. [Universidad de Guanajuato, Dapartamento de Quimica, Noria Alta s/n, 36050 Guanajuato, Gto. (Mexico); Delgado, F. [IPN, Escuela Nacional de Ciencias Biologicas, Departamento de Quimica Organica, Prol. Carpio y Plan de Ayala s/n, 11340 Mexico D. F. (Mexico); Alcaraz, Y.; FRobles, J.; Martinez A, M., E-mail: mvazquez@ugto.mx [Universidad de Guanajuato, Departamento de Farmacia, Noria Alta s/n, 36050 Guanajuato, Gto. (Mexico)

    2014-10-01

    An alternative is presented by promoting a reaction with infrared irradiation to obtain different 4-aryl-3-cyano-5-ethoxycarbonyl-6-methyl-2-pyridone derivatives 9 a-k. The process was carried out with a green approach from the corresponding 4 H-pyrans, using mild reaction conditions and infrared irradiation as the energy source. In the first stage, the reaction produced 1,2,3,4-tetrahydropyridine-2-one derivatives 8 a-k, followed by an oxidative step to afford the target molecules in good yields. The structure of products 9 a-k was confirmed by Ft-IR, {sup 1}H NMR and {sup 13}C NMR spectroscopic techniques and X-ray diffraction. It was found that the efficiency of the reaction depends on the catalyst and the solvent, as well as on the aldehyde substituents. (Author)

  9. Improving the Performance of Gold-Nanoparticle-Doped Solid-State Dye Laser Using Thermal Conversion Effect

    Science.gov (United States)

    An, N. T. M.; Lien, N. T. H.; Hoang, N. D.; Hoa, D. Q.

    2018-04-01

    Energy transfer between spherical gold nanoparticles with size of more than 15 nm and molecules of organic dye 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4 H-pyran (DCM) has been studied. Such radiative energy transfer led to high local temperature, giving rise to a bleaching effect that resulted in rapid degradation of the laser medium. Gold nanoparticles were dispersed at concentrations from 5 × 109 particles/mL to 5 × 1010 particles/mL in DCM polymethylmethacrylate polymer using a radical polymerization process with 2,2'-azobis(isobutyronitrile) (AIBN) as initiator. Using the fast thermoelectric cooling method, the laser medium stability was significantly improved. The output stability of a distributed feedback dye laser pumped by second-harmonic generation from a neodymium-doped yttrium aluminum garnet (Nd:YAG) laser was investigated. Moreover, bidirectional energy transfer between gold nanoparticles and dye molecules was observed.

  10. Discovery and Characterization of CD12681, a Potent RORγ Inverse Agonist, Preclinical Candidate for the Topical Treatment of Psoriasis.

    Science.gov (United States)

    Ouvry, Gilles; Atrux-Tallau, Nicolas; Bihl, Franck; Bondu, Aline; Bouix-Peter, Claire; Carlavan, Isabelle; Christin, Olivier; Cuadrado, Marie-Josée; Defoin-Platel, Claire; Deret, Sophie; Duvert, Denis; Feret, Christophe; Forissier, Mathieu; Fournier, Jean-François; Froude, David; Hacini-Rachinel, Fériel; Harris, Craig Steven; Hervouet, Catherine; Huguet, Hélène; Lafitte, Guillaume; Luzy, Anne-Pascale; Musicki, Branislav; Orfila, Danielle; Ozello, Benjamin; Pascau, Coralie; Pascau, Jonathan; Parnet, Véronique; Peluchon, Guillaume; Pierre, Romain; Piwnica, David; Raffin, Catherine; Rossio, Patricia; Spiesse, Delphine; Taquet, Nathalie; Thoreau, Etienne; Vatinel, Rodolphe; Vial, Emmanuel; Hennequin, Laurent François

    2018-02-20

    With possible implications in multiple autoimmune diseases, the retinoic acid receptor-related orphan receptor RORγ has become a sought-after target in the pharmaceutical industry. Herein are described the efforts to identify a potent RORγ inverse agonist compatible with topical application for the treatment of skin diseases. These efforts culminated in the discovery of N-(2,4-dimethylphenyl)-N-isobutyl-2-oxo-1-[(tetrahydro-2H-pyran-4-yl)methyl]-2,3-dihydro-1H-benzo[d]imidazole-5-sulfonamide (CD12681), a potent inverse agonist with in vivo activity in an IL-23-induced mouse skin inflammation model. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  11. Rhodomollacetals A-C, PTP1B Inhibitory Diterpenoids with a 2,3:5,6-Di-seco-grayanane Skeleton from the Leaves of Rhododendron molle.

    Science.gov (United States)

    Zhou, Junfei; Sun, Na; Zhang, Hanqi; Zheng, Guijuan; Liu, Junjun; Yao, Guangmin

    2017-10-06

    Three novel diterpenoids with an unprecedented 2,3:5,6-di-seco-grayanane carbon skeleton, rhodomollacetals A-C (1-3), are isolated from the leaves of Rhododendron molle. Their structures are elucidated by comprehensive spectroscopic techniques and single-crystal X-ray diffraction. Rhodomollacetal A (1) possesses a novel cis/cis/cis/cis-fused 6/6/6/6/5 pentacyclic ring system, featuring an unprecedented 11,13,18-trioxa-pentacyclo [8.7.1.1 5,8 .0 2,8 .0 12,17 ]nonadecane scaffold. Compounds 2 and 3 have a rare 4-oxatricyclo[7.2.1.0 1,6 ]dodecane moiety and a 2,3-dihydro-4H-pyran-4-one unit. Compounds 1-3 showed moderate PTP1B inhibitory activities, and their molecular dockings were investigated.

  12. Gamma radiation induced enhancement in the antioxidant and radioprotective activities of flavonoids

    International Nuclear Information System (INIS)

    Arul Anantha Kumar, A.; Sonwani, Swetha; Bakkiam, D.

    2018-01-01

    Recently γ-radiation has been used as a tool to induce structural changes in natural biomolecules to enhance their biological and physiological properties. Flavonoids are a family of plant derived polyphenolic compounds having considerable scientific and therapeutic importance. Structurally they are the benzo-γ-pyrone derivatives containing phenolic and pyrane rings. Flavonoid radioprotection is an intense area of research thanks to features like natural origin, effectiveness at non-toxic dose levels and lack of side effects. But till date no report is available on the effect of γ-radiation mediated enhancement in radioprotection activity of flavonoids. In view of this the present study was carried out to determine the γ-radiation induced structural changes in selected flavonoids i.e. apigenin, naringenin and genistein and also to explore the possibility of enhancement in their antioxidant and radioprotective activities

  13. Liposomes as vehicles for water insoluble platinum-based potential drug

    DEFF Research Database (Denmark)

    Kaluđerović, Goran N; Dietrich, Andrea; Kommera, Harish

    2012-01-01

    -flow fractionation indicating size of around 120 nm. Stability study showed that LipoTHP-C11 was stable at 4 °C for more than two months. To test suitability of chosen formulation, LipoTHP-C11 was investigated against several tumor cell lines: H12.1, 1411HP, 518A2, A549, HT-29, MCF-7 and SW1736. Furthermore......Formulation of liposome delivery system loaded with water insoluble 2-(4-(tetrahydro-2H-pyran-2-yloxy)-undecyl)-propane-1,3-diamminedichloroplatinum(II), LipoTHP-C11 was carried out. The particle size distributions were determined by dynamic light scattering and asymmetrical flow field......, toxicity against normal fibroblasts was examined. LipoTHP-C11 may be used as an attractive candidate for further assessment in vivo as antitumor agent....

  14. Discovery of Selective Phosphodiesterase 1 Inhibitors with Memory Enhancing Properties.

    Science.gov (United States)

    Dyck, Brian; Branstetter, Bryan; Gharbaoui, Tawfik; Hudson, Andrew R; Breitenbucher, J Guy; Gomez, Laurent; Botrous, Iriny; Marrone, Tami; Barido, Richard; Allerston, Charles K; Cedervall, E Peder; Xu, Rui; Sridhar, Vandana; Barker, Ryan; Aertgeerts, Kathleen; Schmelzer, Kara; Neul, David; Lee, Dong; Massari, Mark Eben; Andersen, Carsten B; Sebring, Kristen; Zhou, Xianbo; Petroski, Robert; Limberis, James; Augustin, Martin; Chun, Lawrence E; Edwards, Thomas E; Peters, Marco; Tabatabaei, Ali

    2017-04-27

    A series of potent thienotriazolopyrimidinone-based PDE1 inhibitors was discovered. X-ray crystal structures of example compounds from this series in complex with the catalytic domain of PDE1B and PDE10A were determined, allowing optimization of PDE1B potency and PDE selectivity. Reduction of hERG affinity led to greater than a 3000-fold selectivity for PDE1B over hERG. 6-(4-Methoxybenzyl)-9-((tetrahydro-2H-pyran-4-yl)methyl)-8,9,10,11-tetrahydropyrido[4',3':4,5]thieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one was identified as an orally bioavailable and brain penetrating PDE1B enzyme inhibitor with potent memory-enhancing effects in a rat model of object recognition memory.

  15. A Novel Schiff Base of 3-acetyl-4-hydroxy-6-methyl-(2Hpyran-2-one and 2,2'-(ethylenedioxydiethylamine as Potential Corrosion Inhibitor for Mild Steel in Acidic Medium

    Directory of Open Access Journals (Sweden)

    Jonnie N. Asegbeloyin

    2015-05-01

    Full Text Available The corrosion inhibition activity of a newly synthesized Schiff base (SB from 3-acetyl-4-hydroxy-6-methyl-(2H-pyran-2-one and 2,2'-(ethylenedioxydiethylamine was investigated on the corrosion of mild steel in 1 M HCl solution using potentiodynamic polarization and electrochemical impedance spectroscopic techniques. Ultraviolet-visible (UV-vis and Raman spectroscopic techniques were used to study the chemical interactions between SB and mild steel surface. SB was found to be a relatively good inhibitor of mild steel corrosion in 1 M HCl. The inhibition efficiency increases with increase in concentration of SB. The inhibition activity of SB was ascribed to its adsorption onto mild steel surface, through physisorption and chemisorption, and described by the Langmuir adsorption model. Quantum chemical calculations indicated the presence of atomic sites with potential nucleophilic and electrophilic characteristics with which SB can establish electronic interactions with the charged mild steel surface.

  16. Ecocatalysis for 2H-chromenes synthesis: an integrated approach for phytomanagement of polluted ecosystems.

    Science.gov (United States)

    Escande, Vincent; Velati, Alicia; Grison, Claude

    2015-04-01

    A direct, general and efficient method to synthesize 2H-chromenes (2H-benzo[b]pyrans), identified as environmentally friendly pesticides, has been developed. This approach lays on the new concept of ecocatalysis, which involves the use of biomass from phytoextraction processes, as a valuable source of metallic elements for chemical synthesis. This methodology is similar or superior to known methods, affording 2H-chromenes with good to excellent yields (60-98%), including the preparation of precocene I, a natural insect growth regulator, with 91% yield. The approach is ideal for poor reactive substrates such as phenol or naphthol, classically transformed into 2H-chromenes by methodologies associated with environmental issues. These results illustrate the interest of combining phytoextraction and green synthesis of natural insecticides.

  17. Chemical Constituents of Luffa acutangula (L.) Roxb Fruit

    Science.gov (United States)

    Suryanti, V.; Marliyana, S. D.; Astuti, I. Y.

    2017-04-01

    The phytochemical screening conducted on ethanol extract of Luffa acutangula (L.) Roxb’s fruit revealed the presence of alkaloids, saponins, carotenoids and terpenoids and the absence of flavonoids, tannins and anthraquinones. The GC-MS of the analysis L. acutangula (L.) Roxb’s fraction resulted in the identification of six compounds. The compounds that could be identified were 2,3-dihydro,3,5-dihydroxy-6-methyl-(4H)-pyran-4-one; 3,7,11,15-tetramethyl-2-hexadecen-1-ol; (3β, 20R)-cholest-5-en-3-ol; n-hexadecanoic acid; 9, 12, 15-octadecatrienoic acid methyl ester and citronellyl tiglate. The present study provides evidence that L. acutangula’s fruit contains medicinally important bioactive compounds and this justifies the possibly use of these fruits as traditional medicine for treatment of various diseases.

  18. Structure analysis and laxative effects of oligosaccharides isolated from bananas.

    Science.gov (United States)

    Wang, Juan; Huang, Hui Hua; Cheng, Yan Feng; Yang, Gong Ming

    2012-10-01

    Banana oligosaccharides (BOS) were extracted with water, and then separated and purified using column chromatography. Gel penetration chromatography was used to determine the molecular weights. Thin layer chromatogram and capillary electrophoresis were employed to analyze the monosaccharide composition. The indican bond and structure of the BOS molecule were determined using Fourier transform infrared spectroscopy and nuclear magnetic resonance. Results showed that BOS were probably composed of eight β-D-pyran glucose units linked with 1→6 indican bonds. The laxative effects of BOS were investigated in mice using the method described in "Handbook of Technical Standards for Testing and Assessment of Health Food in China." The length of the small intestine over which a carbon suspension solution advanced in mice treated with low-, middle-, and high-dose BOS was significantly greater than that in the model group, suggesting that BOS are effective in accelerating the movement of the small intestine.

  19. Plastic lab-on-a-chip for fluorescence excitation with integrated organic semiconductor lasers.

    Science.gov (United States)

    Vannahme, Christoph; Klinkhammer, Sönke; Lemmer, Uli; Mappes, Timo

    2011-04-25

    Laser light excitation of fluorescent markers offers highly sensitive and specific analysis for bio-medical or chemical analysis. To profit from these advantages for applications in the field or at the point-of-care, a plastic lab-on-a-chip with integrated organic semiconductor lasers is presented here. First order distributed feedback lasers based on the organic semiconductor tris(8-hydroxyquinoline) aluminum (Alq3) doped with the laser dye 4-dicyanomethylene-2-methyl-6-(p-dimethylaminostyril)-4H-pyrane (DCM), deep ultraviolet induced waveguides, and a nanostructured microfluidic channel are integrated into a poly(methyl methacrylate) (PMMA) substrate. A simple and parallel fabrication process is used comprising thermal imprint, DUV exposure, evaporation of the laser material, and sealing by thermal bonding. The excitation of two fluorescent marker model systems including labeled antibodies with light emitted by integrated lasers is demonstrated.

  20. Antibacterial Bisabolane-Type Sesquiterpenoids from the Sponge-Derived Fungus Aspergillus sp.

    Directory of Open Access Journals (Sweden)

    Chang-Yun Wang

    2012-01-01

    Full Text Available Four new bisabolane-type sesquiterpenoids, aspergiterpenoid A (1, (−-sydonol (2, (−-sydonic acid (3, and (−-5-(hydroxymethyl-2-(2′,6′,6′-trimethyltetrahydro-2H- pyran-2-ylphenol (4 together with one known fungal metabolite (5 were isolated from the fermentation broth of a marine-derived fungus Aspergillus sp., which was isolated from the sponge Xestospongia testudinaria collected from the South China Sea. Four of them (1–4 are optically active compounds. Their structures and absolute configurations were elucidated by using NMR spectroscopic techniques and mass spectrometric analysis, and by comparing their optical rotations with those related known analogues. Compounds 1–5 showed selective antibacterial activity against eight bacterial strains with the MIC (minimum inhibiting concentrations values between 1.25 and 20.0 µM. The cytotoxic, antifouling, and acetylcholinesterase inhibitory activities of these compounds were also examined.

  1. Threshold effect under nonlinear limitation of the intensity of high-power light

    International Nuclear Information System (INIS)

    Tereshchenko, S A; Podgaetskii, V M; Gerasimenko, A Yu; Savel'ev, M S

    2015-01-01

    A model is proposed to describe the properties of limiters of high-power laser radiation, which takes into account the threshold character of nonlinear interaction of radiation with the working medium of the limiter. The generally accepted non-threshold model is a particular case of the threshold model if the threshold radiation intensity is zero. Experimental z-scan data are used to determine the nonlinear optical characteristics of media with carbon nanotubes, polymethine and pyran dyes, zinc selenide, porphyrin-graphene and fullerene-graphene. A threshold effect of nonlinear interaction between laser radiation and some of investigated working media of limiters is revealed. It is shown that the threshold model more adequately describes experimental z-scan data. (nonlinear optical phenomena)

  2. Characterisation of the Broadly-Specific O-Methyl-transferase JerF from the Late Stages of Jerangolid Biosynthesis

    Directory of Open Access Journals (Sweden)

    Steffen Friedrich

    2016-10-01

    Full Text Available We describe the characterisation of the O-methyltransferase JerF from the late stages of jerangolid biosynthesis. JerF is the first known example of an enzyme that catalyses the formation of a non-aromatic, cyclic methylenolether. The enzyme was overexpressed in E. coli and the cell-free extracts were used in bioconversion experiments. Chemical synthesis gave access to a series of substrate surrogates that covered a broad structural space. Enzymatic assays revealed a broad substrate tolerance and high regioselectivity of JerF, which makes it an attractive candidate for an application in chemoenzymatic synthesis with particular usefulness for late stage application on 4-methoxy-5,6-dihydro-2H-pyran-2-one-containing natural products.

  3. (R,S-2′-Amino-6′-methyl-2,5′,5′-trioxo-6′H-spiro[indoline-3,4′-pyrano[3,2-c][2,1]benzothiazine]-3′-carbonitrile dimethylformamide monosolvate

    Directory of Open Access Journals (Sweden)

    Svitlana V. Shishkina

    2014-07-01

    Full Text Available The title solvate, C20H14N4O4S·C3H7NO, comprises a stereogenic centre but the centrosymmetric space group causes the presence of the racemate in the crystal. The spiro-joined fragments are almost orthogonal, with a dihedral angle of 86.8 (2° between the mean planes of the pyrane ring and the dihydroindolone ring system. The atoms of the indolinone bicycle are coplanar, with an r.m.s. deviation of 0.005 Å. In the crystal, pairs of N—H...O hydrogen bonds link the molecules into centrosymmetric dimers which are linked to the dimethylformamide solvent molecules by further N—H...O hydrogen bonds. N—H...N hydrogen bonds link neighbouring dimers into [010] chains.

  4. (S,S,S,S-Nebivolol hydrochloride hemihydrate

    Directory of Open Access Journals (Sweden)

    Yoann Rousselin

    2012-12-01

    Full Text Available The asymmetric unit of the title hydrated salt, C22H26F2NO4+·Cl−·0.5H2O, consists of an (S,S,S,S-nebivolol {nebivol = bis[2-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl-2-hydroxyethyl]ammonium} cation, a chloride anion and a half-occupancy water molecule. The dihedral angle between the mean planes of the benzene rings is 50.34 (12°. The pyran rings adopt half-chair conformations. The crystal packing features O—H...O hydrogen bonds and weak N—H...Cl, O—H...Cl, and O—H...Cl interactions, producing layers along (010.

  5. Three-component reactions of kojic acid: Efficient synthesis of Dihydropyrano[3,2-b]chromenediones and aminopyranopyrans catalyzed with Nano-Bi2O3-ZnO and Nano-ZnO

    Directory of Open Access Journals (Sweden)

    Maryam Zirak

    2017-05-01

    Full Text Available Synthesis of pyrano-chromenes and pyrano-pyrans was developed by three-component reactions of kojic acid and aromatic aldehydes with dimethone and malononitrile, catalyzed with nano-Bi2O3-ZnO and nano-ZnO, respectively. Reactions proceeded smoothly and the corresponding heterocyclic products were obtained in good to high yields. Nano ZnO and nano Bi2O3-ZnO were prepared by sol-gel method and characterized by X-ray diffraction (XRD, energy-dispersive X-ray analysis (EDX, Fourier transform infrared (FT-IR, scanning electron microscopy (SEM, and transmission electron microscopy (TEM techniques. Supporting Bi3+ on ZnO nanoparticles as Bi2O3, is the main novelty of this work. The simple reaction procedure, easy separation of products, low catalyst loading, reusability of the catalyst are some advantageous of this protocol.

  6. A new coruleoellagic acid derivative from stems of Rhodamnia dumetorum.

    Science.gov (United States)

    Lakornwong, Waranya; Kanokmedhakul, Kwanjai; Kanokmedhakul, Somdej

    2018-07-01

    A new coruleoellagic acid derivative, 3,3',4,4',5'-pentamethylcoruleoellagic acid (1) together with nine known compounds, hexamethylcoruleoellagic acid (2), 3,4,3'-tri-O-methylellagic acid (3), heptaphylline (4), 7-methoxymukonal (5), dentatin (6), sinapaldehyde (7), gallic acid (8), 2,6-dimethoxy-4H-pyran-4-one (9) and β-sitosterol (10) were isolated from the stems of Rhodamnia dumetorum. Their structures were identified by physical and spectroscopic data (IR, 1D and 2D NMR, and MS). Compounds 1, 2 and 7-10 were tested for antibacterial activity against six pathogenic bacterial strains (Bacillus cereus, Escherichia coli, Pseudomonas aeruginosa, Salmonella enterica serovar Typhimurium, Staphylococcus aureus, and Methicillin resistant S. aureus (MRSA)).

  7. Assembly of Four Diverse Heterocyclic Libraries Enabled by Prins Cyclization, Au-Catalyzed Enyne Cycloisomerization, and Automated Amide Synthesis

    Science.gov (United States)

    Cui, Jiayue; Chai, David I.; Miller, Christopher; Hao, Jason; Thomas, Christopher; Wang, JingQi; Scheidt, Karl A.; Kozmin, Sergey A.

    2013-01-01

    We describe a unified synthetic strategy for efficient assembly of four new heterocyclic libraries. The synthesis began by creating a range of structurally diverse pyrrolidinones or piperidinones. Such compounds were obtained in a simple one-flask operation starting with readily available amines, ketoesters, and unsaturated anhydrides. The use of tetrahydropyran-containing ketoesters, which were rapidly assembled by our Prins cyclization protocol, enabled efficient fusion of pyran and piperidinone cores. A newly developed Au(I)-catalyzed cycloisomerization of alkyne-containing enamides further expanded heterocyclic diversity by providing rapid entry into a wide range of bicyclic and tricyclic dienamides. The final stage of the process entailed diversification of each of the initially produced carboxylic acids using a fully automated platform for amide synthesis, which delivered 1872 compounds in high diastereomeric and chemical purity. PMID:22860634

  8. A green approach to the production of 2-pyridone derivatives promoted by infrared irradiation

    International Nuclear Information System (INIS)

    Hernandez, F.; De la Cruz, F.; Lopez, J.; Pena, E.; Vazquez, M. A.; Delgado, F.; Alcaraz, Y.; FRobles, J.; Martinez A, M.

    2014-01-01

    An alternative is presented by promoting a reaction with infrared irradiation to obtain different 4-aryl-3-cyano-5-ethoxycarbonyl-6-methyl-2-pyridone derivatives 9 a-k. The process was carried out with a green approach from the corresponding 4 H-pyrans, using mild reaction conditions and infrared irradiation as the energy source. In the first stage, the reaction produced 1,2,3,4-tetrahydropyridine-2-one derivatives 8 a-k, followed by an oxidative step to afford the target molecules in good yields. The structure of products 9 a-k was confirmed by Ft-IR, 1 H NMR and 13 C NMR spectroscopic techniques and X-ray diffraction. It was found that the efficiency of the reaction depends on the catalyst and the solvent, as well as on the aldehyde substituents. (Author)

  9. All-polymer organic semiconductor laser chips: Parallel fabrication and encapsulation

    DEFF Research Database (Denmark)

    Vannahme, Christoph; Klinkhammer, Sönke; Christiansen, Mads Brøkner

    2010-01-01

    Organic semiconductor lasers are of particular interest as tunable visible laser light sources. For bringing those to market encapsulation is needed to ensure practicable lifetimes. Additionally, fabrication technologies suitable for mass production must be used. We introduce all-polymer chips...... comprising encapsulated distributed feedback organic semiconductor lasers. Several chips are fabricated in parallel by thermal nanoimprint of the feedback grating on 4? wafer scale out of poly(methyl methacrylate) (PMMA) and cyclic olefin copolymer (COC). The lasers consisting of the organic semiconductor...... tris(8- hydroxyquinoline) aluminum (Alq3) doped with the laser dye 4-dicyanomethylene-2- methyl-6-(p-dimethylaminostyril)-4H-pyrane (DCM) are hermetically sealed by thermally bonding a polymer lid. The organic thin film is placed in a basin within the substrate and is not in direct contact to the lid...

  10. High Excitation Transfer Efficiency from Energy Relay Dyes in Dye-Sensitized Solar Cells

    KAUST Repository

    Hardin, Brian E.

    2010-08-11

    The energy relay dye, 4-(Dicyanomethylene)-2-methyl-6-(4- dimethylaminostyryl)-4H-pyran (DCM), was used with a near-infrared sensitizing dye, TT1, to increase the overall power conversion efficiency of a dye-sensitized solar cell (DSC) from 3.5% to 4.5%. The unattached DCM dyes exhibit an average excitation transfer efficiency (EÌ?TE) of 96% inside TT1-covered, mesostructured TiO2 films. Further performance increases were limited by the solubility of DCM in an acetonitrile based electrolyte. This demonstration shows that energy relay dyes can be efficiently implemented in optimized dye-sensitized solar cells, but also highlights the need to design highly soluble energy relay dyes with high molar extinction coefficients. © 2010 American Chemical Society.

  11. Photoinduced intramolecular charge transfer and trans-cis isomerization of the DCM styrene dye. Picosecond and nanosecond laser spectroscopy, high-performance liquid chromatography, and nuclear magnetic resonance studies

    Energy Technology Data Exchange (ETDEWEB)

    Meyer, M.; Mialocq, J.C.; Perly, B. (CNRS, Gif-sur-Yvette (France))

    1990-01-11

    The photoexcitation of 4-(dicyanomethylene)-2-methyl-6-(p-(dimethylamino)styryl)-4H-pyran (DCM) induces a large intramolecular charge transfer (ICT) from the dimethylamino electron-donor group to the dicyanomethylene acceptor group. The dramatic effect of the solvent polarity on the absorption and fluorescence spectra on the one hand and the competition between the nonradiative S{sub 1} {yields} S{sub 0} deactivation and trans {yields} cis isomerization processes on the other hand has been examined. Our results clearly show that DCM isomerization efficiency is very low in the more polar solvents. The S{sub 1} {yields} S{sub 0} internal conversion may intervene at a torsional angle smaller than 90{degree} before reaching the perpendicular configuration.

  12. White organic light emitting devices with hybrid emissive layers combining phosphorescence and fluorescence

    Energy Technology Data Exchange (ETDEWEB)

    Lei Gangtie; Chen Xiaolan; Wang Lei; Zhu Meixiang; Zhu Weiguo [Key Lab of Environmental-friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105 (China); Wang Liduo; Qiu Yong [Key Lab of Organic-Optoelectronics and Molecular Sciences of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084 (China)], E-mail: lgt@xtu.edu.cn

    2008-05-21

    We fabricated a white organic light-emitting diode (WOLED) by hybrid emissive layers which combined phosphorescence with fluorescence. In this device, the thin layer of 4-(dicyanomethylene)-2-(t-butyl)-6-(1, 1, 7, 7-tetramethyljulolidyl-9-enyl)-4H-pyran played the role of undoped red emissive layer which was inserted between two blue phosphorescence emissive layers. The blue phosphorescent dye was bis[(4, 6-difluorophenyl)-pyridinato-N, C{sup 2}] (picolinato) Ir(III), which was doped in the host material, N, N'-dicarbazolyl-1, 4-dimethene-benzene. The WOLED showed stable Commission Internationale de L'Eclairage coordinates and a high efficency of 9.6 cd A{sup -1} when the current density was 1.8 A m{sup -2}. The maximum luminance of the device achieved was 17 400 cd m{sup -2} when the current density was 3000 A m{sup -2}.

  13. The effect of dopant-induced electron traps on spectrum evolution of doped organic light-emitting devices

    Energy Technology Data Exchange (ETDEWEB)

    Zhan, Y.Q. [Surface Physics Laboratory (National Key Laboratory), Lab of Advanced Materials, Fudan University, Shanghai 200433 (China)]. E-mail: yqzhan@fudan.edu.cn; Zhou, J. [Surface Physics Laboratory (National Key Laboratory), Lab of Advanced Materials, Fudan University, Shanghai 200433 (China); Zhou, Y.C. [Surface Physics Laboratory (National Key Laboratory), Lab of Advanced Materials, Fudan University, Shanghai 200433 (China); Wu, Y. [Surface Physics Laboratory (National Key Laboratory), Lab of Advanced Materials, Fudan University, Shanghai 200433 (China); Yang, H. [Surface Physics Laboratory (National Key Laboratory), Lab of Advanced Materials, Fudan University, Shanghai 200433 (China); Li, F.Y. [Surface Physics Laboratory (National Key Laboratory), Lab of Advanced Materials, Fudan University, Shanghai 200433 (China); Ding, X.M. [Surface Physics Laboratory (National Key Laboratory), Lab of Advanced Materials, Fudan University, Shanghai 200433 (China); Hou, X.Y. [Surface Physics Laboratory (National Key Laboratory), Lab of Advanced Materials, Fudan University, Shanghai 200433 (China)]. E-mail: xyhou@fudan.edu.cn

    2007-05-07

    A prototype of light emitting device with two symmetrically located Al/LiF electrodes is fabricated to study the voltage dependence of emission spectra. 4-(dicyanomethylene)-2-methyl-6- (pdimethylaminostyryl)-4H-pyran doped tris-(8-hydroxy-quinolinato) aluminum thin film is the emitting layer of the device. Experiments show that with increasing applied voltage the emission intensity of the device decreases, of which the dopant emission intensity decreases more steeply than that of the host. Based on the theory of space-charge-limited current in insulator with a single shallow trap level it is deduced that the photoluminescence intensity of the dopant emission decreases linearly with applied voltage, in good agreement with experimental measurements. The evolution of the emission spectra can be well explained by the suggested mechanism that the electrons are trapped in the dopant molecules, which blocks the energy transfer from the host, and leads to more excitons in the host to emit light.

  14. White emission from organic light-emitting diodes with a super-thin BCP layer

    Energy Technology Data Exchange (ETDEWEB)

    Hao Jingang [Key Laboratory of Luminescence and Optical Information, Ministry of Education, Institute of Optoelectronic Technology, Beijing Jiaotong University, Beijing 100044 (China); Deng Zhenbo [Key Laboratory of Luminescence and Optical Information, Ministry of Education, Institute of Optoelectronic Technology, Beijing Jiaotong University, Beijing 100044 (China)]. E-mail: zbdeng@center.njtu.edu.cn; Yang Shengyi [Key Laboratory of Luminescence and Optical Information, Ministry of Education, Institute of Optoelectronic Technology, Beijing Jiaotong University, Beijing 100044 (China)

    2007-01-15

    We report a method to achieve white emission from organic light-emitting diodes (OLEDs) in which a super-thin (3 nm) hole blocking layer, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), was inserted between electron-transport layer 8-hydroxyquinoline aluminum (Alq{sub 3}) and 4-(dicyanomethylene)-2-t-butyl-6(1,1,7,7-tetramethyljulolidyl-9-enyl) -4H-pyran (DCJTB) doped poly-vinlycarbazole (PVK) layer. The BCP layer can not only confine exciton in the emitting layer but also control energy transfer proportion from PVK to Alq{sub 3} and then from Alq{sub 3} to DCJTB through BCP layer. In this way, pure white emission with CIE coordinate of (0.32, 0.32) was obtained and it was voltage independent. The brightness reached 270 cd/m{sup 2} at 18 V with an efficiency of 0.166 cd/A.

  15. Improved efficiency of organic light-emitting diodes based on a europium complex by fluorescent dye

    Energy Technology Data Exchange (ETDEWEB)

    You Han [State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Graduate School of Chinese Academy of Sciences, Changchun 130022 (China); Fang Junfeng [State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Graduate School of Chinese Academy of Sciences, Changchun 130022 (China); Gao Jia [State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Graduate School of Chinese Academy of Sciences, Changchun 130022 (China); Ma Dongge [State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Graduate School of Chinese Academy of Sciences, Changchun 130022 (China)]. E-mail: mdg1014@ciac.jl.cn

    2007-01-15

    Improved efficiency of organic light-emitting diodes (OLEDs) based on europium complexes have been realized by using a fluorescent dye 4-(dicyanomethylene)-2-t-butyl-6 (1,1,7,7-tetramethyljulolidyl-9-enyl))-4H-pyran (DCJTB) doping .The luminous efficiency of the devices with a fluorescent dye in the emissive layer was found to improve two times of that in devices without fluorescent dye. The devices showed pure red light, which is the characteristic emission of trivalent europium ion with a full-width at half-maximum of 3 nm.The maximum brightness and luminous efficiency reached 1200 cd/m{sup 2} at 23 V and 7.3 cd/A (2.0 lm/w), respectively, at a current density of 0.35 mA/cm{sup 2}.

  16. Effect of dye-doped concentration on the charge carrier recombination in molecularly doped organic light-emitting devices

    Energy Technology Data Exchange (ETDEWEB)

    Chen Jiangshan; Ma Dongge [State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Graduate School of the Chinese Academy of Sciences, Changchun 130022 (China)

    2006-05-21

    The effect of the concentration of 4-(dicyanomethylene)-2-t-butyl-6- (1, 1, 7, 7-tetramethyljulolidyl-9-enyl)-4H-pyran (DCJTB) as dopant in tris(8-hydroxyquinoline) aluminium (Alq{sub 3}) on the charge carrier recombination was studied by transient electroluminescence (EL). The electron-hole recombination coefficient ({gamma}) was determined from the long-time component of the temporal decay of the EL intensity after a rectangular voltage pulse was turned off. It was found that the coefficient monotonically decreased with an increase in the DCJTB-doping concentration. The monotonic decrease is attributed to concentration quenching on the excitons and coincided well with the reduction of the EL efficiency.

  17. Charge-trapping effect of doped fluorescent dye on the electroluminescent processes and its performance in polymer light-emitting diodes

    Energy Technology Data Exchange (ETDEWEB)

    Ye Tengling; Chen Zhenyu; Chen Jiangshan [State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Graduate School of Chinese Academy of Sciences, Changchun 130022 (China); Ma Dongge, E-mail: mdg1014@ciac.jl.cn [State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Graduate School of Chinese Academy of Sciences, Changchun 130022 (China)

    2010-11-15

    We have measured the temperature dependence of the steady-state current-voltage (I-V) characteristics and the transient electroluminescent (EL) characteristics in 4-(dicyanomethylene)-2-t-propyl-6-(1,1,7, 7-tetramethyljulolidyl-9-enyl)-4H-pyran (DCJTB) doped polyfluorene devices to study the charge-trapping effect of DCJTB fluorescent dye on luminescence processes and on device performance. Physical and chemical analyses prove that DCJTB molecules serve both as electron and hole traps, and the charge-trapping effect is more sensitive against the electrons than the holes at the low dopant concentration. This intrinsic characteristic causes the electron to be injected into the emitting layer first and then trapped in the bulk, producing a strong effect on device performance.

  18. Improved outcoupling of light in organic light emitting devices, utilizing a holographic DFB-structure

    Energy Technology Data Exchange (ETDEWEB)

    Reinke, Nils [Organische Funktionsmaterialien, University of Duisburg-Essen (Germany)]. E-mail: nils.reinke@physik.uni-augsburg.de; Fuhrmann, Thomas [Macromolecular Chemistry and Molecular Materials, University of Kassel (Germany); Perschke, Alexandra [Organische Funktionsmaterialien, University of Duisburg-Essen (Germany); Franke, Hilmar [Organische Funktionsmaterialien, University of Duisburg-Essen (Germany)

    2004-12-10

    In this work organic light emitting devices (OLEDs) were fabricated implementing gratings, in order to extract waveguided electroluminescence (EL). The gratings were recorded by exposing thin films of the molecular azo glass N, N'-bis (4-phenyl)-N, N'-bis [(4-phenylazo)-phenyl] benzidine (AZOPD) to holographic light patterns. The photopatterned AZOPD serves as hole transport material for devices with aluminum-tris(8-hydroxyquinoline) doped with 1% of 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran (Alq{sub 3}:DCM) as emissive/electron transport layer. The corrugated devices showed enhanced emission in the forward direction. The emitted light is polarized preferably parallel to the grating lines. In addition, we have found a doubling in the total luminance with respect to the unstructured device.

  19. The effect of DCJTB doping concentration in PVK on the chromatic coordinate of electroluminescence

    Energy Technology Data Exchange (ETDEWEB)

    Zhang, F J; Xu, Z; Zhao, S L; Wang, L W; Yuan, G C [Key Laboratory of Luminescence and Optical Information (Beijing Jiaotong University), Ministry of Education (China); Zhao, D W [School of Electrical and Electronic Engineering, Nanyang Technological University, Nanyang Avenue, Singapore 639798 (Singapore)], E-mail: fjzhang@bjtu.edu.cn

    2008-05-15

    The dominant mechanism of electroluminescence (EL) from 4-(dicyanomethylene)-2-t-butyl-6-(1,1,7,7-tetramethyljulolidyl-9-enyl) -4H-pyran (DCJTB) doped in poly-(N-vinyl-carbazole) (PVK) system was demonstrated to be a charge carrier trapped by DCJTB molecular rather than Foerster energy transfer from PVK to DCJTB. The chromatically coordinate EL emission of PVK:DCJTB changes from (0.41, 0.31) to (0.67, 0.31) with an increase in DCJTB doping concentration. The emission peak in DCJTB shows red-shift and the shoulder emission peak at 656 nm becomes stronger as the doping concentration increases. The effect of DCJTB doping concentration on EL spectra is attributed to strong dipole-dipole interaction between the DCJTB molecule with an increase in doping concentration.

  20. 7-Chloro-4-oxo-4H-chromene-3-carbaldehyde

    Directory of Open Access Journals (Sweden)

    Yoshinobu Ishikawa

    2014-08-01

    Full Text Available In the title compound, C10H5ClO3, a chlorinated 3-formylchromone derivative, all atoms are essentially coplanar (r.m.s. deviation = 0.0592 Å for all non-H atoms, with the largest deviation from the least-squares plane [0.1792 (19 Å] being for the chromone-ring carbonyl O atom. In the crystal, molecules are linked through C—H...O hydrogen bonds to form tetrads, which are assembled by stacking interactions [centroid–centroid distance between the pyran rings = 3.823 (3 Å] and van der Waals contacts between the Cl atoms [Cl...Cl = 3.4483 (16 Å and C—Cl...Cl = 171.73 (7°] into a three-dimensional architecture.

  1. Crystal structure of ethyl (2S-9-methoxy-2-methyl-4-oxo-3,4,5,6-tetrahydro-2H- 2,6-methanobenzo[g][1,3,5]oxadiazocine-11-carboxylate

    Directory of Open Access Journals (Sweden)

    A. Dhandapani

    2015-02-01

    Full Text Available In the title compound, C15H18N2O5, the methoxyphenyl ring makes a dihedral angle of 84.70 (12° with the mean plane of the tetrahydropyrimidin-2(1H-one ring. Both the pyran and tetrahydropyrimidin-2(1H-one rings have distorted envelope conformations with the carboxylate-substituted C atom as the flap. In the crystal, molecules are linked via pairs of N—H...O hydrogen bonds, forming zigzag chains propagating along [010], which enclose R22(8 ring motifs. The chains are linked by C—H...π interactions, forming a two-dimensional network parallel to (100.

  2. The effect of dopant-induced electron traps on spectrum evolution of doped organic light-emitting devices

    International Nuclear Information System (INIS)

    Zhan, Y.Q.; Zhou, J.; Zhou, Y.C.; Wu, Y.; Yang, H.; Li, F.Y.; Ding, X.M.; Hou, X.Y.

    2007-01-01

    A prototype of light emitting device with two symmetrically located Al/LiF electrodes is fabricated to study the voltage dependence of emission spectra. 4-(dicyanomethylene)-2-methyl-6- (pdimethylaminostyryl)-4H-pyran doped tris-(8-hydroxy-quinolinato) aluminum thin film is the emitting layer of the device. Experiments show that with increasing applied voltage the emission intensity of the device decreases, of which the dopant emission intensity decreases more steeply than that of the host. Based on the theory of space-charge-limited current in insulator with a single shallow trap level it is deduced that the photoluminescence intensity of the dopant emission decreases linearly with applied voltage, in good agreement with experimental measurements. The evolution of the emission spectra can be well explained by the suggested mechanism that the electrons are trapped in the dopant molecules, which blocks the energy transfer from the host, and leads to more excitons in the host to emit light

  3. A fluorescence switch based on a controllable photochromic naphthopyran group

    International Nuclear Information System (INIS)

    Chen Lizhen; Wang Guang; Zhao Xiancai

    2011-01-01

    A fluorescence switch based on photoisomerization of naphthopyran (NP) has been designed by employing 2-(pyridin-2-yl)-benzimidazole (BPI) and the naphthopyran containing two pyran rings (NP) as fluorescent dye and photochromic compound, respectively. The fluorescence switch of benzimidazole derivative can be modulated either by controlling the irradiation time of UV light or by adjusting the amount ratio of fluorescent benzimidazole derivative to photochromic naphthopyran in both solution and polymethyl methacrylate (PMMA) film. The experimental results indicated that the decrease of fluorescence intensity of benzimidazole derivative is attributed to the interaction of benzimidazole with naphthopyran. - Highlights: → Naphthopyran was first used to fabricate fluorescence switch with benzimidazole derivative. → Fluorescence intensity can be modulated by controlling the UV irradiation time. → Fluorescence intensity can be adjusted by changing the ratio of benzimidazole derivative to naphthopyran. → Decrease of fluorescence intensity is attributed to the interaction of benzimidazole derivative and naphthopyran.

  4. White emission from organic light-emitting diodes with a super-thin BCP layer

    International Nuclear Information System (INIS)

    Hao Jingang; Deng Zhenbo; Yang Shengyi

    2007-01-01

    We report a method to achieve white emission from organic light-emitting diodes (OLEDs) in which a super-thin (3 nm) hole blocking layer, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), was inserted between electron-transport layer 8-hydroxyquinoline aluminum (Alq 3 ) and 4-(dicyanomethylene)-2-t-butyl-6(1,1,7,7-tetramethyljulolidyl-9-enyl) -4H-pyran (DCJTB) doped poly-vinlycarbazole (PVK) layer. The BCP layer can not only confine exciton in the emitting layer but also control energy transfer proportion from PVK to Alq 3 and then from Alq 3 to DCJTB through BCP layer. In this way, pure white emission with CIE coordinate of (0.32, 0.32) was obtained and it was voltage independent. The brightness reached 270 cd/m 2 at 18 V with an efficiency of 0.166 cd/A

  5. The Structure–Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation

    Science.gov (United States)

    Bow, Eric W.; Rimoldi, John M.

    2016-01-01

    The cannabinoids are members of a deceptively simple class of terpenophenolic secondary metabolites isolated from Cannabis sativa highlighted by (−)-Δ9-tetrahydrocannabinol (THC), eliciting distinct pharmacological effects mediated largely by cannabinoid receptor (CB1 or CB2) signaling. Since the initial discovery of THC and related cannabinoids, synthetic and semisynthetic classical cannabinoid analogs have been evaluated to help define receptor binding modes and structure–CB1/CB2 functional activity relationships. This perspective will examine the classical cannabinoids, with particular emphasis on the structure–activity relationship of five regions: C3 side chain, phenolic hydroxyl, aromatic A-ring, pyran B-ring, and cyclohexenyl C-ring. Cumulative structure–activity relationship studies to date have helped define the critical structural elements required for potency and selectivity toward CB1 and CB2 and, more importantly, ushered the discovery and development of contemporary nonclassical cannabinoid modulators with enhanced physicochemical and pharmacological profiles. PMID:27398024

  6. Novel synthesis on poly (vinyl alcohol): characterization, complexation a biological activity

    International Nuclear Information System (INIS)

    El-Sawy, N.M.; Elassar, A.Z.; Al-Fulaij, O.

    2002-01-01

    Poly(vinyl alcohol), PVA, readily condensed with phenyl hydrazine and malononitrile in basic medium to give the hydrazone and pyran derivatives, respectively. PVA reacted with chloroacetonitrile, biuet and thiophene carbonyl chloride to give modified polymeric materials. While addition of PVA to acrylonitrile and phenyl isothiocyanate gives the ether and thiocarbamate ester derivatives, respectively. Hydroxylamine hydrochloride reacted with the modified, carbonitrile containing, polymer to give the amidoxime derivative. The amidoximated products of PVA and carbamate ester of polymeric material were complexed with CUCL2 solution. The complex materials were confirmed by using UV and ESDS measurements. The morphology of PVA and complex with CUII was observed by SEM. Biological activity of some of the prepared compounds was investigated toward bacteria and fungi

  7. t-Butyl group-substituted triphenylamine-containing orange-red fluorescent emitters for organic light-emitting diodes

    Energy Technology Data Exchange (ETDEWEB)

    Lee, Kum Hee; Kim, Chi Sik [Department of Chemistry, Sungkyunkwan University, Suwon, 440-746 (Korea, Republic of); Kim, Young Kwan, E-mail: kimyk@hongik.ac.kr [Department of Information Display, Hongik University, Seoul 121-791 (Korea, Republic of); Yoon, Seung Soo, E-mail: ssyoon@skku.edu [Department of Chemistry, Sungkyunkwan University, Suwon, 440-746 (Korea, Republic of)

    2012-03-30

    Efficient orange-red fluorescent compounds, 4-(dicyanomethylene)-2-adamantyl-6-(4-(N-(4-tert-butylphenyl) -N-(3,5-di-tert-butylphenyl)amino)benzene)vinyl-4H-pyran (DCATP) and 2,6-bis[4-(N-(4-tert-butylphenyl)-N-(3,5-di-tert-butylphenyl)amino)benzene] vinyl-4-(dicyanomethylene)-4H-pyran (BDCTP) containing the tert-butylated triphenylamine in donor moieties, were synthesized and characterized. In these red emitters, bulky groups, such as t-butyl group and adamantane were introduced to increase the steric hindrance between the red emitters. In particular, an efficient orange-red device containing the emitter DCATP as a dopant showed a luminous and power efficiency of 6.87 cd/A and 2.70 lm/W, respectively, at 20 mA/cm{sup 2} with the CIE coordinates of (0.48, 0.50) at 7.0 V. In addition, an efficient red organic light-emitting diode using BDCTP as a dopant exhibited a luminous and power efficiency of 2.30 cd/A and 1.31 lm/W, respectively, at 20 mA/cm{sup 2} and CIE coordinates of (0.61, 0.39). - Highlights: Black-Right-Pointing-Pointer Two orange-red emitters with t-butylated triphenylamine derivatives were studied. Black-Right-Pointing-Pointer We examine changes in electron D-A and electron D-A-D type in the terminal groups. Black-Right-Pointing-Pointer Electron D-A-D type material shows improved color chromaticity.

  8. Retention of plutonium in mouse tissues as affected by antiviral compounds and their analogs

    International Nuclear Information System (INIS)

    Lindenbaum, A.; Rosenthal, M.W.; Guilmette, R.A.

    1975-01-01

    The chelating agent DTPA (diethylenetriaminepentaacetic acid) is an effective therapeutic substance for decorporation of extracellar monomeric plutonium in the mouse and dog, but is much less effective in removing intracellular polymeric plutonium (Pu-P). In the absence of effective therapy, this intracellular plutonium is long retained in the body, particularly in reticuloendothelial tissues like the liver. Our interest, therefore, turned to the development of adjunct substances capable of removing additional plutonium from the liver beyond that removable by DTPA alone. We showed that glucan, a yeast cell wall polysaccharide, is a useful adjunct to DTPA for removal of Pu-P from the mouse liver. Its toxicity, however, makes it a less than desirable drug for potential human use. Therefore, we initiated a search for more soluble (and presumably less hazardous) therapeutic agents similar to glucan, i.e., capable of adjunct action with DTPA. Of over 20 substances tested the most successful results were obtained with two antiviral, antitumor compounds, the pyran copolymers XA-124-177 and XA-146-85-2. These are condensation products of divinyl ether and maleic anhydride. Another analog, EMH-227, prepared by condensation of acrylic acid and itaconic acid, was similarly successful. Maximal removal of plutonium from mouse liver was obtained with a single intravenous (I.V.) injection of 10 to 90 mg/kg of pyran copolymer given 5 days after I.V. Pu-P administration. Although these doses increased splenic uptake of plutonium, a dose of 10 mg/kg produced a minimal increase in the splenic burden while producing maximal removal of hepatic plutonium

  9. Two novel bioactive glucosinolates from Broccoli (Brassica oleracea L. var. italica) florets.

    Science.gov (United States)

    Survay, Nazneen Shaik; Kumar, Brajesh; Jang, Mi; Yoon, Do-Young; Jung, Yi-Sook; Yang, Deok-Chun; Park, Se Won

    2012-09-01

    Two novel glucosinolates along with one known glucosinolate were isolated from Broccoli (Brassica oleracea L. var. italica) florets. Their structures were established mainly by 1D ((1)H and (13)C NMR), 2D NMR ((1)H-(1)H COSY, DEPT 135°, HSQC and HMBC), and Tandem MS-MS spectrometric data as 2-mercaptomethyl sulfinyl glucosinolate [(Z)-4-(methylsulfinyl)-N-(sulfooxy)-2-((2'S,3'R,4'S,5'S,6'R)-3',4',5'-trihydroxy-6'(hydroxylmethyl)-2'-mercapto tetrahydro-2H-pyran-2-yl) butane amide] 1, (Z)-1-((2S,5S)-5-hydroxytetra-hydro-2H-pyran-2-ylthio)-2-(1H-indol-3-yl) ethylidene amino sulfate 2 and a known cinnamoyl [6'-O-trans-(4″-hydroxy cinnamoyl)4-(methylsulphinyl)butyl glucosinolate] 3. Compound 1 exhibited scavenging activity against DPPH with an inhibitory concentration IC(50) of 20 mM, whereas compound 3 was a weak antioxidant when compared to the standard quercetin (5 mM) as a positive control. Both the compounds showed a significant and similar antimicrobial activity against Staphylococcus aureus with an IC(50) of <625 μg/mL when compared to antibiotic duricef. Against Salmonella typhimurium the IC(50) of 1 and 3 was determined as <625 μg/mL and <1250 μg/mL, respectively, when compared to ampicillin (IC(50) ≤ 39 μg/mL) as a positive control. Copyright © 2012 Elsevier Ltd. All rights reserved.

  10. Laser-limiting materials for medical use

    Science.gov (United States)

    Podgaetsky, Vitaly M.; Kopylova, Tat'yana N.; Tereshchenko, Sergey A.; Reznichenko, Alexander V.; Selishchev, Sergey V.

    2004-03-01

    The important problem of modern laser medicine is the decrease of an exposure of biological tissues outside of an operational field and can be solved by optical radiation limiting. Organic dyes with reversibly darkening can be placed onto surfaces of irradiated tissues or can be introduced in solder for laser welding of vessels. The limiting properties of a set of nontoxic organic compounds were investigated. Nonlinear optical properties of dyes having reverse saturable absorption (pyran styryl derivatives, cyanine and porphyrine compounds) were studied under XeCl and YAG:Nd (II harmonics) lasers excitation. The effect of attenuation of a visible laser radiation is obtained for ethanol solutions of cyanines: radiation attenuation coefficient ( AC) = 25-35 at N/S = 100-250 MW/cm2. In water solutions of such compounds in UV spectrum range AC ~ 10. The spectral characteristics of compounds appeared expedient enough to operational use in laser limiters (broad passband in visible range of a spectrum). Under the data of Z-scanning (the scheme F/10) value AC ~ 70 was reached. The limiting of power laser radiation in visible (λ = 532 nm) and UV- (λ = 308 nm) spectral region and nanosecond pulse duration (7 -13 ns) across porphyrine solutions and their complexes with some metals (13 compounds) was investigated too. The comparative study of optical limiting dependence on intensity of laser radiation, solvent type and concentration of solutions was carried out for selecte wavelength. There was shown a possible use of pyran styryl derivatives DCM as limiters of visual laser radiation. To understand a mechanism of laser radiation limitation the light induced processes were experimentally and theoretically studied in organic molecules. The quantum-chemical investigation of one cyanine compound was carried out. There were noted the perspectives of laser radiation limiting by application of inverted schemes of traditional laser shutters. Usage of phenomena of light -induced

  11. Removal of aflatoxin M1 from artificially contaminated yoghurt by using of new synthesized dehydroacetic acid analogues

    Directory of Open Access Journals (Sweden)

    Frane Delaš

    2012-09-01

    Full Text Available Dehydroacetic acid (DHA and its new synthesized analogues, 4-hydroxy-3-(p-toluoyl-6-(ptolyl-2H-pyrane-2-one (DHT and 5-Bromo-4-hydroxy-3-(p-toluoyl-6-(p-tolyl-2H-pyrane-2-one (BrDHT were tested for removal of aflatoxin M1 (AFM1 from artificially contaminated yoghurt with known concentrations of this toxin to determine the possible use of these chemicals as a means of controlling AFM1 accumulation. Yoghurt from cow’s milk was artificially contaminated with AFM1 at levels of 0.01 to 0.5 μg/L. Yoghurts were stored at 4 °C and 7 °C, respectively, for up to 28 days. Analysis of AFM1 in yoghurt was carried out using two dimensional thin-layer chromatography (TLC - visual estimation. The limit of detection was 0.15 ng/L. The recoveries of AFM1 from the samples spiked at levels of 10, 50, 100, and 500 ng/L were between 80.6 and 107.8 %, respectively. Concentrations of DHA and DHT of 0.01 and 0.03 μmol/L had non or little effect on AFM1 content in experimentally contaminated yoghurt, whereas concentrations higher than 0.05 μmol/L, partially inhibited AFM1 content. The percentage loss of the initial AFM1 amount in yoghurt was estimated by about 15 and 25 %, and 22 to 45 % by the end of storage, respectively. In experiments with 0.01 and 0.05 μmol/L of BrDHT or higher, the concentration of AFM1 was reduced after 28 days by 20 to 95 % or completely, respectively, depending on the time and temperature of deposit. Detection of toxicity of investigated analogues was evaluated by using the brine shrimp (Artemia salina larvae as a screening system for the determination of their sensitivity to some chemicals

  12. Fungal Endophyte Diversity and Bioactivity in the Indian Medicinal Plant Ocimum sanctum Linn.

    Directory of Open Access Journals (Sweden)

    Kanika Chowdhary

    Full Text Available Endophytic mycopopulation isolated from India's Queen of herbs Tulsi (Ocimum sanctum were explored and investigated for their diversity and antiphytopathogenic activity against widespread plant pathogens Botrytis cinerea, Sclerotinia sclerotiorum, Rhizoctonia solani and Fusarium oxysporum. 90 fungal isolates, representing 17 genera were recovered from 313 disease-free and surface sterilised plant segments (leaf and stem tissues from three different geographic locations (Delhi, Hyderabad and Mukteshwar during distinct sampling times in consequent years 2010 and 2011 in India. Fungal endophytes were subjected to molecular identification based on rDNA ITS sequence analysis. Plant pathogens such as F. verticillioides, B. maydis, C. coarctatum, R. bataticola, Hypoxylon sp., Diaporthe phaseolorum, Alternaria tenuissima and A. alternata have occurred as endophyte only during second sampling (second sampling in 2011 in the present study. Bi-plot generated by principal component analysis suggested tissue specificity of certain fungal endophytes. Dendrogram revealed species abundance as a function of mean temperature of the location at the time of sampling. Shannon diversity in the first collection is highest in Hyderabad leaf tissues (H' = 1.907 whereas in second collection it was highest from leaf tissues of Delhi (H' = 1.846. Mukteshwar (altitude: 7500 feet reported least isolation rate in second collection. Nearly 23% of the total fungal isolates were considered as potent biocontrol agent. Hexane extract of M. phaseolina recovered from Hyderabad in first collection demonstrated highest activity against S. sclerotiorum with IC50 value of 0.38 mg/ml. Additionally, its components 2H-pyran-2-one, 5,6-dihydro-6-pentyl and palmitic acid, methyl ester as reported by GC-MS Chromatogram upon evaluation for their antiphytopathogenic activity exhibited IC50 value of 1.002 and 0.662 against respectively S. sclerotiorum indicating their significant role in

  13. SINTESIS SENYAWA C18H26O9 DARI HIPTOLIDA HASIL ISOLASI DAUN HYPTIS PECTINATA

    Directory of Open Access Journals (Sweden)

    Meiny Suzery

    2012-05-01

    Full Text Available SYNTHESIS OF C18H26O9 COMPOUNDS FROM HYPTOLIDE ISOLATED FROM HYPTIS PECTINATA LEAVES. Isolation of hyptolide has been done from Hyptis pectinata, and alkene group transformation through oxidation reactions using H3B: OEt2 to the isolated compound was also conducted. Product analyses were carried out using TLC, UV spectrometry, IR, and LC-MS. Pure crystal with melting point of 86-87oC was isolated. The yield was 1.75% (w/w. After analysing and compilating of spectroscopic data it was confirmed as hyptolide compound. Hydroboration of this compound (followed by hydrolysis using H2O2 under alkaline conditions produce its alcohol derivatives, with 28.9% the percentage of transformation, it was demonstrated by LCMS data. IR spectrum at 3600cm-1, confirming the replacement of hydroxyl bond by alkene. Regioselectivity of addition reaction is proposed through simulation with Chem Office. The reaction product was suspected as 6-hydroxy-7-(6-oxo-3,6-dihydro-2H-pyran-2-yl heptane-2,3,5-tryil triacetate. Extension of reaction time to 24 hours, has increase hydroboration product to 78.3%. This research has opened other studies of natural materials in accordance to the roadmap set.  Telah dilakukan isolasi hiptolida dari bahan alam Hyptis pectinata, dan transformasinya melalui reaksi oksidasi menggunakan H3B:OEt2 terhadap gugus alkena pada senyawa hasil isolasi. Analisis produk dilakukan menggunakan KLT, spektrometri UV, IR, dan LC-MS. Kristal murni dengan titik leleh 86-87oC berhasil diisolasi dengan rendemen 1,75 % (b/b, dirujuk sebagai senyawa hiptolida setelah melalui analisis dan kompilasi data-data spektroskopi. Hidroborasi terhadap senyawa hiptolida (yang diikuti hidrolisis menggunakan H2O2 dalam suasana basa menghasilkan senyawa alkohol turunannya, dengan persentase transformasi sebesar 28,9%, dapat ditunjukkan melalui data LCMS. Data spectrum IR menunjukkan adanya puncak pada 3600cm-1, memperkuat dugaan  adanya ikatan hidroksil menggantikan gugus

  14. Chemical Profile of Monascus ruber Strains

    Directory of Open Access Journals (Sweden)

    Ahamed M. Moharram

    2012-01-01

    Full Text Available Chemical profile of Monascus ruber strains has been studied using gas chromatography-mass spectrometry (GC/MS analysis. The colour intensity of the red pigment and secondary metabolic products of two M. ruber strains (AUMC 4066 and AUMC 5705 cultivated on ten different media were also studied. Metabolic products can be classified into four categories: anticholesterol, anticancer, food colouring, and essential fatty acids necessary for human health. Using GC/MS, the following 88 metabolic products were detected: butyric acid and its derivatives (25 products, other fatty acids and their derivatives (19 products, pyran and its derivatives (22 products and other metabolites (22 products. Among these, 32 metabolites were specific for AUMC 4066 strain and 34 for AUMC 5705 strain, whereas 22 metabolites were produced by both strains on different tested substrates. Production of some metabolites depended on the substrate used. High number of metabolites was recorded in the red pigment extract obtained by both strains grown on malt broth and malt agar. Also, 42 aroma compounds were recorded (4 alcohols, 2 benzaldehydes, 27 esters, 3 lactones, 1 phenol, 1 terpenoid, 3 thiol compounds and acetate-3-mercapto butyric acid. Thin layer chromatography and GC/MS analyses revealed no mycotoxin citrinin in any media used for the growth of the two M. ruber strains.

  15. Development of a see-through hollow cathode discharge lamp for (Li/Ne) optogalvanic studies

    Science.gov (United States)

    Saini, V. K.; Kumar, P.; Sarangpani, K. K.; Dixit, S. K.; Nakhe, S. V.

    2017-09-01

    Development of a demountable and see-through hollow cathode (HC) discharge lamp suitable for optogalvanic (OG) spectroscopy is described. The design of the HC lamp is simple, compact, and inexpensive. Lithium, investigated rarely by the OG method, is selected for cathode material as its isotopes are important for nuclear industry. The HC lamp is characterized electrically and optically for discharge oscillations free OG effect. Strong OG signals of lithium as well as neon (as buffer gas) are produced precisely upon copper vapor laser pumped tunable dye laser irradiation. The HC lamp is capable of generating a clean OG resonance spectrum in the available dye laser wavelength scanning range (627.5-676 nm) obtained with 4-(Dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran dye. About 28 resonant OG lines are explicitly observed. Majority of them have been identified using j-l coupling scheme and assigned to the well-known neon transitions. One line that corresponds to wavelength near about 670.80 nm is assigned to lithium and resolved for its fine (2S1/2 → 2P1/2, 3/2) transitions. These OG transitions allow 0.33 cm-1 accuracy and can be used to supplement the OG transition data available from other sources to calibrate the wavelength of a scanning dye laser with precision at atomic levels.

  16. A new class of analogues of the bifunctional radiosensitizer alpha-(1-aziridinylmethyl)-2-nitro-1H-imidazole-1-ethanol (RSU 1069): The cycloalkylaziridines

    International Nuclear Information System (INIS)

    Suto, M.J.; Stier, M.A.; Werbel, L.M.; Arundel-Suto, C.M.; Leopold, W.R.; Elliott, W.E.; Sebolt-Leopold, J.S.

    1991-01-01

    A series of compounds related to alpha-(1-aziridinylmethyl)-2-nitro-1H-imidazole-1-ethanol (RSU 1069, 1) were synthesized and evaluated as selective hypoxic cell cytotoxic agents and as radiosensitizers. The aziridine moiety was replaced with a number of other potential alkylating groups including cycloalkylaziridines and azetidines. The data indicated that modification of the aziridine of 1 resulted in a substantial decrease in the ability of the compounds to selectively kill hypoxic cells. However, these modifications did not affect the compounds' in vitro radiosensitizing activity since many of the derivatives were as potent as 1. All of the compounds that were evaluated in vivo were less toxic than 1, and several members of this series had significant activity. The best compound was trans-alpha-[[(4-bromotetrahydro-2H-pyran-3-yl) amino]methyl]-2-nitro-1H-imidazole-1-ethanol (18), which, due to its activity and log P value, is a candidate for additional in vivo studies

  17. Modulation of a fluorescence switch based on photochromic spirooxazine in composite organic nanoparticles

    Energy Technology Data Exchange (ETDEWEB)

    Sheng Xiaohai [Beijing National Laboratory for Molecular Sciences (BNLMS), Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080 (China); Peng Aidong [Beijing National Laboratory for Molecular Sciences (BNLMS), Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080 (China); Fu Hongbing [Beijing National Laboratory for Molecular Sciences (BNLMS), Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080 (China); Liu Yuanyuan [Beijing National Laboratory for Molecular Sciences (BNLMS), Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080 (China); Zhao Yongsheng [Beijing National Laboratory for Molecular Sciences (BNLMS), Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080 (China); Ma Ying [Beijing National Laboratory for Molecular Sciences (BNLMS), Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080 (China); Yao Jiannian [Beijing National Laboratory for Molecular Sciences (BNLMS), Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080 (China)

    2007-04-11

    We describe a versatile and convenient approach to achieve fluorescence modulation by the preparation of composite nanoparticles (CNPs), based on photochromic 5-methoxy-1,3,3-trimethyl-9'-hydroxyspiroindolinenaphthoxazine (SO), fluorescent 4-(dicyanomethylene)-2-methyl-6-(p-dimethyl-aminostyryl)-4H-pyran (DCM), and emissive-assistant 1,3-bis(pyrene) propane (BPP) molecules, employing doping techniques. The mechanism of the fluorescence switch is the intermolecular energy transfer as supported by both steady-state and time-resolved spectroscopy results. The addition of BPP not only enhances the contrast of the fluorescence signal between the 'ON' and 'OFF' state, but also provides a convenient way to tune the excitation wavelength for reading the fluorescence. High-contrast ON/OFF (20:1) fluorescence switching is successfully implemented in the CNPs and also in a more practical PVA film loaded with the CNPs. This system may represent an alternative to the covalent system in potentially rewritable high-density optical data or image storage utilizing luminescence intensity readout schemes.

  18. Identification of prenylated pterocarpans and other isoflavonoids in Rhizopus spp. elicited soya bean seedlings by electrospray ionisation mass spectrometry.

    Science.gov (United States)

    Simons, Rudy; Vincken, Jean-Paul; Bohin, Maxime C; Kuijpers, Tomas F M; Verbruggen, Marian A; Gruppen, Harry

    2011-01-15

    Phytoalexins from soya are mainly characterised as prenylated pterocarpans, the glyceollins. Extracts of non-soaked and soaked soya beans, as well as that of soya seedlings, grown in the presence of Rhizopus microsporus var. oryzae, were screened for the presence of prenylated flavonoids with a liquid chromatography/mass spectrometry (LC/MS)-based screening method. The glyceollins I-III and glyceollidins I-II, belonging to the isoflavonoid subclass of the pterocarpans, were tentatively assigned. The formation of these prenylated pterocarpans was accompanied by that of other prenylated isoflavonoids of the subclasses of the isoflavones and the coumestans. It was estimated that approx. 40% of the total isoflavonoid content in Rhizopus-challenged soya bean seedlings were prenylated pterocarpans, whereas 7% comprised prenylated isoflavones and prenylated coumestans. The site of prenylation (A-ring or B-ring) of the prenylated isoflavones was tentatively annotated using positive-ion mode MS by comparing the (1,3) A(+) retro-Diels-Alder (RDA) fragments of prenylated and non-prenylated isoflavones. Furthermore, the fragmentation pathways of the five pterocarpans in negative-ion (NI) mode were proposed, which involved the cleavage of the C-ring and/or D-ring. The absence of the ring-closed prenyl (pyran or furan) gave exclusively -H(2) O(x,y) RDA fragments, whereas its presence gave predominantly the common RDA fragments. Copyright © 2010 John Wiley & Sons, Ltd.

  19. Phytochemical Profile of Erythrina variegata by Using High-Performance Liquid Chromatography and Gas Chromatography-Mass Spectroscopy Analyses.

    Science.gov (United States)

    Muthukrishnan, Suriyavathana; Palanisamy, Subha; Subramanian, Senthilkumar; Selvaraj, Sumathi; Mari, Kavitha Rani; Kuppulingam, Ramalingam

    2016-08-01

    Natural products derived from plant sources have been utilized to treat patients with numerous diseases. The phytochemical constituents present in ethanolic leaf extract of Erythrina variegata (ELEV) were identified by using high-performance liquid chromatography (HPLC) and gas chromatography-mass spectroscopy (GC-MS) analyses. Shade dried leaves were powdered and extracted with ethanol for analyses through HPLC to identify selected flavonoids and through GC-MS to identify other molecules. The HPLC analysis of ELEV showed the presence of gallic and caffeic acids as the major components at concentrations of 2.0 ppm and 0.1 ppm, respectively, as well as other components. GC-MS analysis revealed the presence of 3-eicosyne; 3,7,11,15-tetramethyl-2-hexadecen-1-ol; butanoic acid, 3-methyl-3,7-dimethyl-6-octenyl ester; phytol; 1,2-benzenedicarboxylic acid, diundecyl ester; 1-octanol, 2-butyl-; squalene; and 2H-pyran, 2-(7-heptadecynyloxy) tetrahydro-derivative. Because pharmacopuncture is a new evolving natural mode that uses herbal extracts for treating patients with various ailments with minimum pain and maximum effect, the results of this study are particularly important and show that ELEV possesses a wide range of phytochemical constituents, as indicated above, as effective active principle molecules that can be used individually or in combination to treat patients with various diseases. Copyright © 2016. Published by Elsevier B.V.

  20. Structure elucidation and chemical synthesis of stigmolone, a novel type of prokaryotic pheromone.

    Science.gov (United States)

    Hull, W E; Berkessel, A; Plaga, W

    1998-09-15

    Approximately 2 micromol of a novel prokaryotic pheromone, involved in starvation-induced aggregation and formation of fruiting bodies by the myxobacterium Stigmatella aurantiaca, were isolated by a large-scale elution procedure. The pheromone was purified by HPLC, and high-resolution MS, IR, 1H-NMR, and 13C-NMR were used to identify the active substance as the hydroxy ketone 2,5, 8-trimethyl-8-hydroxy-nonan-4-one, which has been named stigmolone. The analysis was complicated by a solvent-dependent equilibrium between stigmolone and the cyclic enol-ether 3,4-dihydro-2,2, 5-trimethyl-6-(2-methylpropyl)-2H-pyran formed by intramolecular nucleophilic attack of the 8-OH group at the ketone C4 followed by loss of H2O. Both compounds were synthesized chemically, and their structures were confirmed by NMR analysis. Natural and synthetic stigmolone have the same biological activity at ca. 1 nM concentration.

  1. Excitation dynamics of dye doped tris(8-hydroxy quinoline) aluminum films studied using time-resolved photoelectron spectroscopy

    International Nuclear Information System (INIS)

    Read, K.; Karlsson, H. S.; Murnane, M. M.; Kapteyn, H. C.; Haight, R.

    2001-01-01

    In this work, we use excite-probe photoelectron spectroscopy to study the decay of electronic excitation in tris(8-hydroxy quinoline) aluminum (Alq) doped with the organic dye 4-dicyanomethylene-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran (DCM). Ultrashort laser pulses are used to photoexcite electrons into unoccupied molecular orbitals, and the ensuing decay rate is directly observed using photoelectron spectroscopy. Decay of the electronic excitation is studied as a function of DCM doping percentage and excitation intensity. The decay rate is seen to increase with both doping percentage and excitation intensity. These data are explained using a model including Foerster transfer, stimulated emission, concentration quenching, and bimolecular singlet - singlet exciton annihilation. In this model, we find that it is necessary to include a very fast (faster than predicted in standard Foerster transfer theory) excitation transfer of a fraction of the excitation from the Alq to the DCM, where that fraction corresponds to the approximate nearest-neighbor population. [copyright] 2001 American Institute of Physics

  2. Structure-activity relationships and molecular docking of thirteen synthesized flavonoids as horseradish peroxidase inhibitors.

    Science.gov (United States)

    Mahfoudi, Reguia; Djeridane, Amar; Benarous, Khedidja; Gaydou, Emile M; Yousfi, Mohamed

    2017-10-01

    For the first time, the structure-activity relationships of thirteen synthesized flavonoids have been investigated by evaluating their ability to modulate horseradish peroxidase (HRP) catalytic activity. Indeed, a modified spectrophotometrically method was carried out and optimized using 4-methylcatechol (4-MC) as peroxidase co-substrate. The results show that these flavonoids exhibit a great capacity to inhibit peroxidase with Ki values ranged from 0.14±0.01 to 65±0.04mM. Molecular docking has been achieved using Auto Dock Vina program to discuss the nature of interactions and the mechanism of inhibition. According to the docking results, all the flavonoids have shown great binding affinity to peroxidase. These molecular modeling studies suggested that pyran-4-one cycle acts as an inhibition key for peroxidase. Therefore, potent peroxidase inhibitors are flavonoids with these structural requirements: the presence of the hydroxyl (OH) group in 7, 5 and 4' positions and the absence of the methoxy (O-CH 3 ) group. Apigenin contributed better in HRP inhibitory activity. The present study has shown that the studied flavonoids could be promising HRP inhibitors, which can help in developing new molecules to control thyroid diseases. Copyright © 2017 Elsevier Inc. All rights reserved.

  3. Study of the contribution of massoia lactone to the aroma of Merlot and Cabernet Sauvignon musts and wines.

    Science.gov (United States)

    Pons, Alexandre; Allamy, Lucile; Lavigne, Valérie; Dubourdieu, Denis; Darriet, Philippe

    2017-10-01

    Organic extracts of musts and red wines marked by dried fruit and cooked fruit aromas were analyzed by gas chromatography coupled to olfactometry and mass spectrometry. Thanks to this analytical approach we identified a fragrant lactone corresponding to an odorant zone reminiscent of coconut and dried figs as 5,6-dihydro-6-pentyl-2H-pyran-2-one (C10 massoia lactone). Using chiral GC-GC-MS, we show that only the (R)-C10 massoia lactone is found in musts and wines. Its detection thresholds were 10µg/L and 11µg/L in must and wine model solution, respectively. In Merlot and Cabernet Sauvignon musts marked by dried fruit flavors from overripe grapes, its concentration reached 68µg/L. In contrast, in wines marked by these flavors, it never exceeded 20µg/L. We show that (R)-C10 massoia lactone is reduced to (R)-δ-decalactone during alcoholic fermentation. In addition, we underline the contribution of temperature during the growing season on its level in old red wines. Copyright © 2017 Elsevier Ltd. All rights reserved.

  4. Molecular imprinted polymer-coated optical fiber sensor for the identification of low molecular weight molecules.

    Science.gov (United States)

    Lépinay, Sandrine; Ianoul, Anatoli; Albert, Jacques

    2014-10-01

    A biomimetic optical probe for detecting low molecular weight molecules (maltol, 3-hydroxy-2-methyl-4H-pyran-4-one, molecular weight of 126.11 g/mol), was designed, fabricated, and characterized. The sensor couples a molecular imprinted polymer (MIP) and the Bragg grating refractometry technology into an optical fiber. The probe is fabricated first by inscribing tilted grating planes in the core of the fiber, and then by photopolymerization to immobilize a maltol imprinted MIP on the fiber cladding surface over the Bragg grating. The sensor response to the presence of maltol in different media is obtained by spectral interrogation of the fiber transmission signal. The results showed that the limit of detection of the sensor reached 1 ng/mL in pure water with a sensitivity of 6.3 × 10(8)pm/M. The selectivity of the sensor against other compounds and its reusability were also studied experimentally. Finally, the unambiguous detection of concentrations as little as 10nM of maltol in complex media (real food samples) by the MIP-coated tilted fiber Bragg grating sensor was demonstrated. Copyright © 2014 Elsevier B.V. All rights reserved.

  5. {alpha},{beta}-Unsaturated Fischer carbene complexes as chemical multitalents

    Energy Technology Data Exchange (ETDEWEB)

    Meijere, A. de [Institut fuer Organische Chemie der George-August-Universitaet Goettingen (Germany)

    1995-12-31

    The well established reaction of {alpha},{beta}-unsaturated Fischer carbenechromium complexes 6(R{sup 1} = H) with alkynes normally proceeds with carbonyl insertion to yield 4-alkoxyphenols 9. Led by the incidental formation of a cyclopentadiene 3 from certain {beta}-aminosubstituted complexes 6(X = NR{sub 2}{sup 3}, R{sup 1} = cPr) the authors have studied the influences of the nature of substituents (R{sup 1}, X on 6; R{sub L}, R{sub S} in the alkyne; R{sup 3} in the amino group), solvents, and temperature on the outcome of the reaction. Imino substitution on complexes 6 leads to 2H-pyrroles 1, a free primary amino group (X = NH{sub 2}) to pyridines 5, and bulky substituents R{sup 1} to cyclopenta[b]pyrans 8 with double insertion of an alkyne. Eventually, appropriate conditions have been developed which permit to selectively prepare either 3-alkoxy-5-(dialkylamino)cyclopentadienes 3 (as synthetic equivalents of cyclopentenones 4), 5-(dialkylaminomethylene)cyclopent-2-enones 7, 3-alkoxy-2-(1{prime}-morpholino-1{prime}-alkenyl)cyclopent-2-enones 10, and 2-acyl-3-(dialkylamino)cyclopent-2-enones 11 from easily accessible carbene complexes 6 (X = NR{sub 2}{sup 3}) in high yields. Mechanistic aspects and implications of these novel transformations will be discussed.

  6. The relationship between the violet pigment PP-V production and intracellular ammonium level in Penicillium purpurogenum.

    Science.gov (United States)

    Kojima, Ryo; Arai, Teppei; Matsufuji, Hiroshi; Kasumi, Takafumi; Watanabe, Taisuke; Ogihara, Jun

    2016-12-01

    Penicillium purpurogenum is the fungus that produces an azaphilone pigment. However, details about the pigment biosynthesis pathway are unknown. The violet pigment PP-V is the one of the main pigments biosynthesized by this fungus. This pigment contains an amino group in a pyran ring as its core structure. We focused on this pigment and examined the relationship between intracellular ammonium concentration and pigment production using glutamine as a nitrogen source. The intracellular ammonium level decreased about 1.5-fold in conditions favoring PP-V production. Moreover, P. purpurogenum was transferred to medium in which it commonly produces the related pigment PP-O after cultivating it in the presence or absence of glutamine to investigate whether this fungus biosynthesizes PP-V using surplus ammonium in cells. Only mycelia cultured in medium containing 10 mM glutamine produced the violet pigment, and simultaneously intracellular ammonium levels decreased under this condition. From comparisons of the amount of PP-V that was secreted with quantity of surplus intracellular ammonium, it is suggested that P. purpurogenum maintains ammonium homeostasis by excreting waste ammonium as PP-V.

  7. Tetrathiapentalene-based organic conductors

    International Nuclear Information System (INIS)

    Misaki, Yohji

    2009-01-01

    The synthesis, structure and properties of tetrathiapentalene-based (TTP) organic conductors are reviewed. Among various TTP-type donors, bis-fused tetrathiafulvalene, 2,5-bis(1,3-dithiol-2-ylidene)-1,3,4,6-tetrathiapentalene (BDT-TTP) and its derivatives afford many metallic radical cation salts stable down to low temperatures, regardless of the size and shape of the counter anions. Most BDT-TTP conductors have a β-type donor arrangement with almost uniform stacks. Introduction of appropriate substituents results in molecular packing that differs from the β-type. A vinylogous TTP, 2-(1,3-dithiol-2-ylidene)-5-(2-ethanediylidene-1,3-dithiole) -1,3,4,6-tetrathiapentalene (DTEDT) has yielded an organic superconductor (DTEDT) 3 Au(CN) 2 as well as metallic radical cation salts, regardless of the counter anions. (Thio)pyran analogs of TTP, namely (T)PDT-TTP and its derivatives produce molecular conductors with novel molecular arrangements. A TTP analog with reduced π-electron system 2,5-bis(1,3-dithian-2-ylidene)-1,3,4,6-tetrathiapentalene (BDA-TTP) has afforded several organic superconductors. Highly conducting molecular metals with unusual oxidation states (+1, +5/3 and neutral) have been developed on the basis of 2,5-bis(1,3-dithiol-2-ylidene)-1,3,4,6-tetrathiapentalene (BDT-TTP) derivatives and analogous metal derivatives M(dt) 2 (M = Ni, Au). (topical review)

  8. Experimental design-based isotope-dilution SPME-GC/MS method development for the analysis of smoke flavouring products.

    Science.gov (United States)

    Giri, Anupam; Zelinkova, Zuzana; Wenzl, Thomas

    2017-12-01

    For the implementation of Regulation (EC) No 2065/2003 related to smoke flavourings used or intended for use in or on foods a method based on solid-phase micro extraction (SPME) GC/MS was developed for the characterisation of liquid smoke products. A statistically based experimental design (DoE) was used for method optimisation. The best general conditions to quantitatively analyse the liquid smoke compounds were obtained with a polydimethylsiloxane/divinylbenzene (PDMS/DVB) fibre, 60°C extraction temperature, 30 min extraction time, 250°C desorption temperature, 180 s desorption time, 15 s agitation time, and 250 rpm agitation speed. Under the optimised conditions, 119 wood pyrolysis products including furan/pyran derivatives, phenols, guaiacol, syringol, benzenediol, and their derivatives, cyclic ketones, and several other heterocyclic compounds were identified. The proposed method was repeatable (RSD% <5) and the calibration functions were linear for all compounds under study. Nine isotopically labelled internal standards were used for improving quantification of analytes by compensating matrix effects that might affect headspace equilibrium and extractability of compounds. The optimised isotope dilution SPME-GC/MS based analytical method proved to be fit for purpose, allowing the rapid identification and quantification of volatile compounds in liquid smoke flavourings.

  9. Ethyl 2-amino-4-(4-bromophenyl-6-methoxy-4H-benzo[h]chromene-3-carboxylate

    Directory of Open Access Journals (Sweden)

    Seik Weng Ng

    2013-03-01

    Full Text Available In the title compound, C23H20BrNO4, the pyran ring has a flattened boat conformation with the O and methine C atoms lying to one side of the plane [0.160 (5 and 0.256 (6 Å, respectively] defined by the remaining atoms. Nevertheless, the 4H-benzo[h]chromene ring system approximates a plane (r.m.s. deviation = 0.116 Å with the bromobenzene ring almost perpendicular [dihedral angle = 83.27 (16°] and the ester group coplanar [C—C—C—O = 3.4 (5°]; the methoxy substituent is also coplanar [C—O—C—C = 174.5 (3°]. In addition to an intramolecular N—H...O(ester carbonyl hydrogen bond, the ester carbonyl O atom also forms an intermolecular N—H...O hydrogen bond with the second amine H atom, generating a zigzag supramolecular chain along the c axis in the crystal packing. The chains are linked into layers in the bc plane by N—H...Br hydrogen bonds, and these layers are consolidated into a three-dimensional architecture by C—H...π interactions.

  10. Chemical Composition of Pyroligneous Acid Obtained from Eucalyptus GG100 Clone

    Directory of Open Access Journals (Sweden)

    Alexandre S. Pimenta

    2018-02-01

    Full Text Available The present study aimed to characterize the chemical composition of pyroligneous acid (PA obtained from slow pyrolysis of the clone GG100 of Eucalyptus urophylla × Eucalyptus grandis. The efficiency of extraction of organic compounds by using different solvents—dichloromethane (DCM, diethyl ether (DE and ethyl acetate (EA—was evaluated. Wood discs were collected and carbonized at a heating rate of 1.25 °C/min until 450 °C. Pyrolysis gases were trapped and condensed, yielding a crude liquid product (CLP, which was refined to obtain pure PA. Then liquid–liquid extraction was carried out. Each extracted fraction was analyzed by GC-MS and the chemical compounds were identified. Experimental results showed that a larger number of chemical compounds could be extracted by using DCM and EA in comparison to diethyl ether DE. A total number of 93 compounds were identified, with phenolic compounds being the major group, followed by aldehydes and ketones, furans, pyrans and esters. Higher contents of guaiacol, phenol, cresols and furfural seem to explain the antibacterial and antifungal activity shown by PA, as reported previously in the literature. Experimental data indicated that the organic phase extracted from GG100 PA consists of a mixture of compounds similar to liquid smokes regularly used in the food industry.

  11. Zinc Enolate/Sulfinate Prepared from a Single-Run Reaction Using Zinc Dust with O-Tosylated 4-Hydroxy Coumarin and Pyrone

    Energy Technology Data Exchange (ETDEWEB)

    Shin, Ueon Sang; Joo, Seong-Ryu; Kim, Seung-Hoi [Dankook University, Cheonan (Korea, Republic of)

    2016-07-15

    We demonstrated the preparation of new zinc complexes, 2-oxo-2H-chromen-4-yloxy tosylzinc (I), and 6-methyl-2-oxo-2H-pyran-4-yloxy tosylzinc (II), by the oxidative addition of readily available zinc dust into the corresponding 4-tosylated coumarin (A) and pyrone (B), respectively. Of special interest, the thus-obtained zinc complexes showed an electrophile-dependent reactivity. The subsequent coupling reactions of I and II with a variety of acid chlorides provided the O-acylation product in moderate yields. More interestingly, it should be emphasized that the thus-prepared zinc complexes (I and II) functioned both as zinc enolate and zinc sulfinate, providing C(3)-disubstituted product (b) and sulfone (c), respectively, from a single-run reaction when I or II was treated with benzyl halides. Even though somewhat low yields were achieved under the nonoptimized conditions, the novel zinc complexes present another potential application for zinc reagents. Versatile applications of this discovery are currently underway.

  12. The colour-tuning effect of 2,9-dimethyl-4,7-diphenyl-1, 10-phenanthroline in blue-red organic light-emitting devices

    International Nuclear Information System (INIS)

    Lin Jian; Xia, Yi-Jie; Tang Chao; Yin Kun; Zhong Gaoyu; Ni Gang; Peng Bo; Hou Xiaoyuan; Gan Fuxi; Huang Wei

    2007-01-01

    This paper reports the fabrication and measurement of organic light-emitting devices comprised of indium-tin-oxide (ITO)/4,4',4-prime-tris(N-carbazolyl)-triphenylamine (TCTA, 8 nm)/2-pyrenyl-9-phenyl-9-pyrenylfluorene(2P9PPF, 30 nm)/ bathocuproine (BCP, with different thickness)/Alq 3 : DCJTB (DCJTB = 4-(dicyanomethylene)-2-t-butyl-6(1,1,7,7- tetramethyljulolidyl-9-enyl)-4H-pyran, Alq 3 = tris(8-hydroxyquinolino) aluminium(III), 2% in mass ratio, 30 nm)/Mg : Ag(250 nm). The dependence of electroluminescence (EL) spectra on the BCP layer thickness and operating voltage has been investigated quantitatively. It is shown that the emission colour of the devices changes from red to blue at 8 V when the BCP layer thickness changes from 1 to 10 nm. The emission colour of the devices also varies with the applying voltage even in a given device. The ratio of blue emission originating from 2P9PPF to the red emission originating from DCJTB increases with the applying voltage. Based on the hole blocking effect of the BCP layer, we deduced the dependence of this ratio on the BCP layer thickness and simulated the experimental result well. It is also proposed that the variation of the EL spectrum with the voltage can be attributed to the varying hole blocking effect under the varying electric field, which resulted in a recombination zone shift, and the exciton dissociation effect in the electric field

  13. Identification of key aromatic compounds in Congou black tea by PLSR with variable importance of projection scores and gas chromatography-mass spectrometry/gas chromatography-olfactometry.

    Science.gov (United States)

    Mao, Shihong; Lu, Changqi; Li, Meifeng; Ye, Yulong; Wei, Xu; Tong, Huarong

    2018-04-13

    Gas chromatography-olfactometry (GC-O) is the most frequently used method to estimate the sensory contribution of single odorant, but disregards the interactions between volatiles. In order to select the key volatiles responsible for the aroma attributes of Congou black tea (Camellia sinensis), instrumental, sensory and multivariate statistical approaches were applied. By sensory analysis, nine panelists developed 8 descriptors, namely, floral, sweet, fruity, green, roasted, oil, spicy, and off-odor. Linalool, (E)-furan linalool oxide, (Z)-pyran linalool oxide, methyl salicylate, β-myrcene, phenylethyl alcohol which identified from the most representative samples by GC-O procedure, were the essential aroma-active compounds in the formation of basic Congou black tea aroma. In addition, 136 volatiles were identified by gas chromatography-mass spectrometry (GC-MS), among which 55 compounds were determined as the key factors for the six sensory attributes by partial least-square regression (PLSR) with variable importance of projection (VIP) scores. Our results demonstrated that HS-SPME/GC-MS/GC-O was a fast approach for isolation and quantification aroma-active compounds. PLSR method was also considered to be a useful tool in selecting important variables for sensory attributes. These two strategies allowed us to comprehensively evaluate the sensorial contribution of single volatile from different perspectives, can be applied to related products for comprehensive quality control. This article is protected by copyright. All rights reserved.

  14. A Novel Method of Imaging Lysosomes in Living Human Mammary Epithelial Cells

    Directory of Open Access Journals (Sweden)

    Kristine Glunde

    2003-01-01

    Full Text Available Cancer cells invade by secreting degradative enzymes which, under normal conditions, are sequestered in lysosomal vesicles. The ability to noninvasively label lysosomes and track lysosomal trafficking would be extremely useful to understand the mechanisms by which degradative enzymes are secreted in the presence of pathophysiological environments, such as hypoxia and acidic extracellular pH, which are frequently encountered in solid tumors. In this study, a novel method of introducing a fluorescent label into lysosomes of human mammary epithelial cells (HMECs was evaluated. Highly glycosylated lysosomal membrane proteins were labeled with a newly synthesized compound, 5-dimethylamino-naphthalene-1-sulfonic acid 5-amino-3,4,6-trihydroxy-tetrahydro-pyran-2-ylmethyl ester (6-O-dansyl-GlcNH2. The ability to optically image lysosomes using this new probe was validated by determining the colocalization of the fluorescence from the dansyl group with immunofluorescent staining of two well-established lysosomal marker proteins, LAMP-1 and LAMP-2. The location of the dansyl group in lysosomes was also verified by using an anti-dansyl antibody in Western blots of lysosomes isolated using isopycnic density gradient centrifugation. This novel method of labeling lysosomes biosynthetically was used to image lysosomes in living HMECs perfused in a microscopy-compatible cell perfusion system.

  15. Introduction of Red-Green-Blue Fluorescent Dyes into a Metal-Organic Framework for Tunable White Light Emission.

    Science.gov (United States)

    Wen, Yuehong; Sheng, Tianlu; Zhu, Xiaoquan; Zhuo, Chao; Su, Shaodong; Li, Haoran; Hu, Shengmin; Zhu, Qi-Long; Wu, Xintao

    2017-10-01

    The unique features of the metal-organic frameworks (MOFs), including ultrahigh porosities and surface areas, tunable pores, endow the MOFs with special utilizations as host matrices. In this work, various neutral and ionic guest dye molecules, such as fluorescent brighteners, coumarin derivatives, 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran (DCM), and 4-(p-dimethylaminostyryl)-1-methylpyridinium (DSM), are encapsulated in a neutral MOF, yielding novel blue-, green-, and red-phosphors, respectively. Furthermore, this study introduces the red-, green-, and blue-emitting dyes into a MOF together for the first time, producing white-light materials with nearly ideal Commission International ed'Eclairage (CIE) coordinates, high color-rendering index values (up to 92%) and quantum yields (up to 26%), and moderate correlated color temperature values. The white light is tunable by changing the content or type of the three dye guests, or the excitation wavelength. Significantly, the introduction of blue-emitting guests in the methodology makes the available MOF host more extensive, and the final white-light output more tunable and high-quality. Such strategy can be widely adopted to design and prepare white-light-emitting materials. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  16. Determination of captopril in biological samples by high-performance liquid chromatography with ThioGlo 3 derivatization.

    Science.gov (United States)

    Aykin, N; Neal, R; Yusof, M; Ercal, N

    2001-11-01

    Captopril, a well-known angiotensin converting enzyme (ACE) inhibitor, is widely used for treatment of arterial hypertension. Recent studies suggest that it may also act as a scavenger of free radicals because of its thiol group. Therefore, the present study describes a rapid, sensitive and relatively simple method for the detection of captopril in biological tissues with reverse-phase HPLC. Captopril was first derivatized with ThioGlo 3 [3H-Naphto[2,1-b]pyran,9-acetoxy-2-(4-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)phenyl-3-oxo-)]. It was then detected by fluorescence-HPLC using an Astec C(18) column as the stationary phase and a water:acetonitrile:acetic acid:phosphoric acid mixture (50:50; 1 mL/L acids) as the mobile phase (excitation wavelength, 365 nm; emission wavelength, 445 nm). The calibration curve for captopril was linear over a range of 10-2500 nM and the coefficient of variation acquired for the within- and between-run precision for captopril was 0.5 and 3.8%, respectively. The detection limit of captopril with this method was found to be 200 fmol/20 microL injection volume. Its relative recovery from biological samples was determined to the range from 93.3 to 105.3%. Based on these results, we believe that our method is advantageous for captopril determination. Copyright 2001 John Wiley & Sons, Ltd.

  17. Constituents of Musa x paradisiaca cultivar with the potential to induce the phase II enzyme, quinone reductase.

    Science.gov (United States)

    Jang, Dae Sik; Park, Eun Jung; Hawthorne, Michael E; Vigo, Jose Schunke; Graham, James G; Cabieses, Fernando; Santarsiero, Bernard D; Mesecar, Andrew D; Fong, Harry H S; Mehta, Rajendra G; Pezzuto, John M; Kinghorn, A Douglas

    2002-10-23

    A new bicyclic diarylheptanoid, rel-(3S,4aR,10bR)-8-hydroxy-3-(4-hydroxyphenyl)-9-methoxy-4a,5,6,10b-tetrahydro-3H-naphtho[2,1-b]pyran (1), as well as four known compounds, 1,2-dihydro-1,2,3-trihydroxy-9-(4-methoxyphenyl)phenalene (2), hydroxyanigorufone (3), 2-(4-hydroxyphenyl)naphthalic anhydride (4), and 1,7-bis(4-hydroxyphenyl)hepta-4(E),6(E)-dien-3-one (5), were isolated from an ethyl acetate-soluble fraction of the methanol extract of the fruits of Musa x paradisiaca cultivar, using a bioassay based on the induction of quinone reductase (QR) in cultured Hepa1c1c7 mouse hepatoma cells to monitor chromatographic fractionation. The structure and relative stereochemistry of compound 1 were elucidated unambiguously by one- and two-dimensional NMR experiments ((1)H NMR, (13)C NMR, DEPT, COSY, HMQC, HMBC, and NOESY) and single-crystal X-ray diffraction analysis. Isolates 1-5 were evaluated for their potential cancer chemopreventive properties utilizing an in vitro assay to determine quinone reductase induction and a mouse mammary organ culture assay.

  18. Identification of bitter compounds in whole wheat bread.

    Science.gov (United States)

    Jiang, Deshou; Peterson, Devin G

    2013-11-15

    Bitterness in whole wheat bread can negatively influence product acceptability and consumption. The overall goal of this project was to identify the main bitter compounds in a commercial whole wheat bread product. Sensory-guided fractionation of the crust (most bitter portion of the bread sample) utilising liquid-liquid extraction, solid-phase extraction, ultra-filtration and 2-D offline RPLC revealed multiple bitter compounds existed. The compounds with the highest bitterness intensities were selected and structurally elucidated based on accurate mass-TOF, MS/MS, 1D and 2D NMR spectroscopy. Eight bitter compounds were identified: Acortatarins A, Acortatarins C, 5-(hydroxymethyl)furfural(HMF), 2,3-dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one (DDMP), N-(1-deoxy-d-fructos-1-yl)-l-tryptophan (ARP), Tryptophol (TRO), 2-(2-formyl-5-(hydroxymethyl-1H-pyrrole-1-yl)butanoic acid (PBA) and Tryptophan (TRP). Based on the structures of these compounds, two main mechanisms of bitterness generation in wheat bread were supported, fermentation and Maillard pathways. Copyright © 2013 Elsevier Ltd. All rights reserved.

  19. Study of various evaporation rates of the mixture of Alq{sub 3}: DCM in a single furnace crucible

    Energy Technology Data Exchange (ETDEWEB)

    Abedi, Zahra; Janghouri, Mohammad [Laser and Plasma Research Institute, Shahid Beheshti University, G.C., Tehran 1983963113 (Iran, Islamic Republic of); Mohajerani, Ezeddin, E-mail: e-mohajerani@sbu.ac.ir [Laser and Plasma Research Institute, Shahid Beheshti University, G.C., Tehran 1983963113 (Iran, Islamic Republic of); Alahbakhshi, Masoud; Azari, Amin [Laser and Plasma Research Institute, Shahid Beheshti University, G.C., Tehran 1983963113 (Iran, Islamic Republic of); Fallahi, Afsoon [Department of Polymer Engineering and Color Technology, Amirkabir University of Technology, 424 Hafez Avenue, P.O. Box 15875-4413, Tehran (Iran, Islamic Republic of)

    2014-03-15

    The emitting color for a new organic light emitting diode (OLED) structure is tuned by doping an appropriate amount of 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran (DCM) orange dye into tris-(8-hydroxyquinoline) aluminum (Alq{sub 3}) emissive layer. Here, the blend of Alq{sub 3}:DCM is deposited in a single furnace crucible by various evaporation rates. The electro-optical behavior of organic light emitting diode devices is greatly influenced by varying the Alq{sub 3}:DCM film composition. It is investigated that when the deposition rate increased from 0.6 to 5 Å/s, complete energy transfer occurred from Alq{sub 3} to DCM and Electroluminescence (EL) peak shifted to higher wavelength regions. The device with evaporation rate of 0.6 Å/s shows a luminance of 3532 cd/m{sup 2} and maximum efficiency of 0.82 cd/A at 20 V. These blends show excellent orange emission host–guest system properties with easier deposition rate control. -- Highlight: • We fabricated light emitting layer by dissolving dyes in common solvent followed by thermal evaporation of dyes. • Achieving orange emissions with a single furnace. • We investigated for the first time Alq{sub 3}:DCM evaporation rate by using single furnace.

  20. Quantum efficiency harmonic analysis of exciton annihilation in organic light emitting diodes

    Energy Technology Data Exchange (ETDEWEB)

    Price, J. S.; Giebink, N. C., E-mail: ncg2@psu.edu [Department of Electrical Engineering, The Pennsylvania State University, University Park, Pennsylvania 16802 (United States)

    2015-06-29

    Various exciton annihilation processes are known to impact the efficiency roll-off of organic light emitting diodes (OLEDs); however, isolating and quantifying their contribution in the presence of other factors such as changing charge balance continue to be a challenge for routine device characterization. Here, we analyze OLED electroluminescence resulting from a sinusoidal dither superimposed on the device bias and show that nonlinearity between recombination current and light output arising from annihilation mixes the quantum efficiency measured at different dither harmonics in a manner that depends uniquely on the type and magnitude of the annihilation process. We derive a series of analytical relations involving the DC and first harmonic external quantum efficiency that enable annihilation rates to be quantified through linear regression independent of changing charge balance and evaluate them for prototypical fluorescent and phosphorescent OLEDs based on the emitters 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran and platinum octaethylporphyrin, respectively. We go on to show that, in most cases, it is sufficient to calculate the needed quantum efficiency harmonics directly from derivatives of the DC light versus current curve, thus enabling this analysis to be conducted solely from standard light-current-voltage measurement data.

  1. Metabolomics by Proton High-Resolution Magic-Angle-Spinning Nuclear Magnetic Resonance of Tomato Plants Treated with Two Secondary Metabolites Isolated from Trichoderma.

    Science.gov (United States)

    Mazzei, Pierluigi; Vinale, Francesco; Woo, Sheridan Lois; Pascale, Alberto; Lorito, Matteo; Piccolo, Alessandro

    2016-05-11

    Trichoderma fungi release 6-pentyl-2H-pyran-2-one (1) and harzianic acid (2) secondary metabolites to improve plant growth and health protection. We isolated metabolites 1 and 2 from Trichoderma strains, whose different concentrations were used to treat seeds of Solanum lycopersicum. The metabolic profile in the resulting 15 day old tomato leaves was studied by high-resolution magic-angle-spinning nuclear magnetic resonance (HRMAS NMR) spectroscopy directly on the whole samples without any preliminary extraction. Principal component analysis (PCA) of HRMAS NMR showed significantly enhanced acetylcholine and γ-aminobutyric acid (GABA) content accompanied by variable amount of amino acids in samples treated with both Trichoderma secondary metabolites. Seed germination rates, seedling fresh weight, and the metabolome of tomato leaves were also dependent upon doses of metabolites 1 and 2 treatments. HRMAS NMR spectroscopy was proven to represent a rapid and reliable technique for evaluating specific changes in the metabolome of plant leaves and calibrating the best concentration of bioactive compounds required to stimulate plant growth.

  2. Metabolites of Trichoderma species isolated from damp building materials.

    Science.gov (United States)

    McMullin, David R; Renaud, Justin B; Barasubiye, Tharcisse; Sumarah, Mark W; Miller, J David

    2017-07-01

    Buildings that have been flooded often have high concentrations of Trichoderma spores in the air while drying. Inhaled spores and spore and mycelial fragments contain large amounts of fungal glucan and natural products that contribute to the symptoms associated with indoor mould exposures. In this study, we considered both small molecules and peptaibol profiles of T. atroviride, T. koningiopsis, T. citrinoviride, and T. harzianum strains obtained from damp buildings in eastern Canada. Twenty-residue peptaibols and sorbicillin-derived metabolites (1-6) including a new structure, (R)-vertinolide (1), were characterized from T. citrinoviride. Trichoderma koningiopsis produced several koninginins (7-10), trikoningin KA V, and the 11-residue lipopeptaibols trikoningin KB I and trikoningin KB II. Trichoderma atroviride biosynthesized a mixture of 19-residue trichorzianine-like peptaibols, whereas T. harzianum produced 18-residue trichokindin-like peptaibols and the 11-residue harzianin HB I that was subsequently identified from the studied T. citrinoviride strain. Two α-pyrones, 6-pentyl-pyran-2-one (11) and an oxidized analog (12), were produced by both T. atroviride and T. harzianum. Aside from exposure to low molecular weight natural products, inhalation of Trichoderma spores and mycelial fragments may result in exposure to membrane-disrupting peptaibols. This investigation contributes to a more comprehensive understanding of the biologically active natural products produced by fungi commonly found in damp buildings.

  3. Tunable organic distributed feedback dye laser device excited through Förster mechanism

    Science.gov (United States)

    Tsutsumi, Naoto; Hinode, Taiki

    2017-03-01

    Tunable organic distributed feedback (DFB) dye laser performances are re-investigated and characterized. The slab-type waveguide DFB device consists of air/active layer/glass substrate. Active layer consisted of tris(8-quinolinolato)aluminum (Alq3), 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran (DCM) dye, and polystyrene (PS) matrix. Effective energy transfer from Alq3 to DCM through Förster mechanism enhances the laser emission. Slope efficiency in the range of 4.9 and 10% is observed at pump energy region higher than 0.10-0.15 mJ cm-2 (lower threshold), which is due to the amplified spontaneous emission (ASE) and lasing. Typical slope efficiency for lasing in the range of 2.0 and 3.0% is observed at pump energy region higher than 0.25-0.30 mJ cm-2 (higher threshold). The tuning wavelength for the laser emission is ranged from 620 to 645 nm depending on the ASE region.

  4. Improvement of amplified spontaneous emission performance by doping tris(8-hydroxyquinoline) aluminum (Alq3) in dye-doped polymer thin films.

    Science.gov (United States)

    Lu, Wu; You, Han; Fang, Junfeng; Ma, Dongge

    2007-04-20

    A well-known red fluorescent dye 4-(dicy-anomethylene)-2-t-butyl-6(1,1,7,7-tetramethyljulolidyl-9-enyl)-4H-pyran (DCJTB) was codoped with an electron transport organic molecule tris(8-hydroxyquinoline) aluminum (Alq(3)) in a host matrix of polystyrene (PS), and the amplified spontaneous emission (ASE) was studied by optically pumping. It was found that the ASE performance was significantly improved by the introduction of Alq(3). The Alq(3):DCJTB:PS blending thin films showed a low threshold (2.4 microJ/pulse) and a high net gain coefficient (109.95 cm(-1)) compared with the pure DCJTB:PS system (threshold of 15.2 microJ/pulse and gain of 35.94 cm(-1)). The improvement of the ASE performance was considered to be attributable to the effective Föster energy transfer from Alq(3) to DCJTB. Our results demonstrate that the Alq(3):DCJTB could be a promising candidate as gain medium for red organic diode lasers.

  5. A new methodology capable of characterizing most volatile and less volatile minor edible oils components in a single chromatographic run without solvents or reagents. Detection of new components.

    Science.gov (United States)

    Alberdi-Cedeño, Jon; Ibargoitia, María L; Cristillo, Giovanna; Sopelana, Patricia; Guillén, María D

    2017-04-15

    The possibilities offered by a new methodology to determine minor components in edible oils are described. This is based on immersion of a solid-phase microextraction fiber of PDMS/DVB into the oil matrix, followed by Gas Chromatography/Mass Spectrometry. It enables characterization and differentiation of edible oils in a simple way, without either solvents or sample modification. This methodology allows simultaneous identification and quantification of sterols, tocols, hydrocarbons of different natures, fatty acids, esters, monoglycerides, fatty amides, aldehydes, ketones, alcohols, epoxides, furans, pyrans and terpenic oxygenated derivatives. The broad information provided by this methodology is useful for different areas of interest such as nutritional value, oxidative stability, technological performance, quality, processing, safety and even the prevention of fraudulent practices. Furthermore, for the first time, certain fatty amides, gamma- and delta-lactones of high molecular weight, and other aromatic compounds such as some esters derived from cinnamic acid have been detected in edible oils. Copyright © 2016 Elsevier Ltd. All rights reserved.

  6. Characterization of substituted aryl meroterpenoids from red seaweed Hypnea musciformis as potential antioxidants.

    Science.gov (United States)

    Chakraborty, Kajal; Joseph, Deepu; Joy, Minju; Raola, Vamshi Krishna

    2016-12-01

    The ethyl acetate fraction of red seaweed Hypnea musciformis was purified to yield three substituted aryl meroterpenoids, namely, 2-(tetrahydro-5-(4-hydroxyphenyl)-4-pentylfuran-3-yl)-ethyl-4-hydroxybenzoate (1), 2-2-[(4-hydroxybenzoyl)-oxy]-ethyl-4-methoxy-4-2-[(4-methylpentyl)oxy]-3,4-dihydro-2H-6-pyranylbutanoic acid (2) and 3-((5-butyl-3-methyl-5,6-dihydro-2H-pyran-2-yl)-methyl)-4-methoxy-4-oxobutyl benzoate (3). The structures of these compounds, as well as their relative stereochemistries, were confirmed by exhaustive NMR spectroscopic data analyses. Compound 1 exhibited similar 2,2'-diphenylpicrylhydrazyl radical inhibiting and Fe(2+) ion chelating activities (IC50 25.05 and 350.7μM, respectively) as that of commercial antioxidant gallic acid (IC50 32.3 and 646.6μM, respectively), followed by 3 (IC50 231.2 and 667.9μM, respectively), and 2 (IC50 322.4 and 5115.3μM, respectively), in descending order of activities. Structure-activity relationship analysis revealed that the antioxidant activities of these compounds were directly proportional to the steric and hydrophobic parameters. The seaweed derived aryl meroterpenoids might serve as potential lead antioxidative molecules for use in pharmaceutical and food industries. Copyright © 2016 Elsevier Ltd. All rights reserved.

  7. Modulation of a fluorescence switch based on photochromic spirooxazine in composite organic nanoparticles

    International Nuclear Information System (INIS)

    Sheng Xiaohai; Peng Aidong; Fu Hongbing; Liu Yuanyuan; Zhao Yongsheng; Ma Ying; Yao Jiannian

    2007-01-01

    We describe a versatile and convenient approach to achieve fluorescence modulation by the preparation of composite nanoparticles (CNPs), based on photochromic 5-methoxy-1,3,3-trimethyl-9'-hydroxyspiroindolinenaphthoxazine (SO), fluorescent 4-(dicyanomethylene)-2-methyl-6-(p-dimethyl-aminostyryl)-4H-pyran (DCM), and emissive-assistant 1,3-bis(pyrene) propane (BPP) molecules, employing doping techniques. The mechanism of the fluorescence switch is the intermolecular energy transfer as supported by both steady-state and time-resolved spectroscopy results. The addition of BPP not only enhances the contrast of the fluorescence signal between the 'ON' and 'OFF' state, but also provides a convenient way to tune the excitation wavelength for reading the fluorescence. High-contrast ON/OFF (20:1) fluorescence switching is successfully implemented in the CNPs and also in a more practical PVA film loaded with the CNPs. This system may represent an alternative to the covalent system in potentially rewritable high-density optical data or image storage utilizing luminescence intensity readout schemes

  8. Photophysical and photochemical study of styrene dyes related to their laser efficiency

    International Nuclear Information System (INIS)

    Meyer, Martine

    1989-01-01

    The photophysical and photochemical properties of two styrene dyes: 4-dicyanomethylene-2-methyl-6-p-dimethylamino-styryl-4H-pyran (DCM) and 7-dimethylamino-3-(-p-formyl-styryl)-1,4-benzoxazine-2-one (DFSBO) have been studied. These molecules have electron donor and electron acceptor groups which give to their fluorescent excited state a charge transfer state character. The red shifts of the absorption and fluorescence spectra in polar solvents and the large Stokes shift related to the increase of the dipole moment from the ground state to the singlet excited state have been fully characterised. The absorption spectra of the first excited singlet and triplet states and the quantum yields of the intersystem crossing to the triplet state have been determined. The existence of conformers of the two dyes has been evidenced. The synthesis of DCM leads to the trans isomer which, under light exposure undergoes photo-isomerization to the cis-compound. Their fluorescence lifetimes and the photo-isomerization efficiency are solvent dependent. The DFSBO emission spectra depend greatly on the excitation wavelength. This effect can be explained by the occurrence of two rotational conformers one being stabilised by an intramolecular hydrogen bond. The spectral properties of these two molecules enable us to explain why DCM is a very good laser dye whereas DFSBO has a poor laser efficiency. (author) [fr

  9. Theoretical and experimental study of the relaxation of excited states of the DCM laser dye. Intra-molecular electron transfer and photo-isomerization. Solvent effects

    International Nuclear Information System (INIS)

    Marguet, Sylvie

    1992-01-01

    This research thesis reports the study of a styrenic laser dye, the 4-(dicyanomethylene)-2-methyl-6-[p-(dimethylamino) styryl]-4H-pyrane or DCM for the characterization of the first electronic states and of the influence of the solvent on efficiencies of different relaxation processes of the first excited state S1 of the DCM. Due to the presence of a combination of a donor group and acceptor group, this compound has interesting properties of intra-molecular charge transfer and of photo-isomerization which highly depend on solvent polarity. Two approaches have been adopted to study these complementary processes: an experimental approach (determination of rate constants of the different deactivation ways of the S1 state by measuring fluorescence quantum efficiencies, photo-isomerization quantum efficiencies, and fluorescence lifetimes of DCM in about twenty solvent of increasing polarity), and a computational approach (a CS-INDO-MRI type quantum chemistry calculation to obtain potential energy curves, charge distributions, and dipolar moments of DCM first electronic states) [fr

  10. Natural products from the ascidian Botrylloides giganteum, from the sponges Verongula gigantea, Ircinia felix, Cliona delitrix and from the nudibranch Tambja eliora, from the Brazilian coastline

    International Nuclear Information System (INIS)

    Granato, Ana Claudia; Oliveira, Jaine H.H.L. de; Seleghim, Mirna H.R.; Berlinck, Roberto G.S.; Macedo, Mario L.; Ferreira, Antonio G.; Rocha, Rosana M. da; Hajdu, Eduardo; Peixinho, Solange; Pessoa, Claudia O.; Moraes, Manoel O.; Cavalcanti, Bruno C.

    2005-01-01

    Two new marine metabolites, 3Z, 6Z, 9Z-dodecatrien-1-ol (1) from the ascidian Botrylloides giganteum and 4H-pyran-2ol acetate from the sponge Ircinia felix (4) are herein reported. The known bromotyrosine compounds, 2-(3,5-dibromo-4-methoxyphenyl)-N,N,Ndimethylethanammonium (2) and 2,6-dibromo-4-(2-(trimethylammonium)ethyl)phenol (3), have been isolated from the sponge Verongula gigantea. Serotonin (5) is reported for the first time from the sponge Cliona delitrix, and tambjamines A (15) and D (16) isolated as their respective salts from the nudibranch Tambja eliora. Only tambjamine D presented cytotoxicity against CEM (IC 5 )0 12.2 μg/mL) and HL60 (IC 50 13.2 μg/mL) human leukemia cells, MCF-7 breast cancer cells (IC 50 13.2 μg/mL), colon HCT-8 cancer cells (IC 50 10.1 μg/mL) and murine melanoma B16 cancer cells (IC 50 6.7 μg/mL). (author)

  11. Crystal structure of 2-methylamino-4-(6-methyl-4-oxo-4H-chromen-3-yl-3-nitropyrano[3,2-c]chromen-5(4H-one with an unknown solvate

    Directory of Open Access Journals (Sweden)

    Rajamani Raja

    2015-09-01

    Full Text Available In the title compound, C23H16N2O7, the mean planes of the two chromene units (r.m.s. deviations = 0.031 and 0.064 Å are almost normal to one another with a dihedral angle of 85.59 (6°. The central six-membered pyran ring has a distorted envelope conformation, with the methine C atom at the flap. There is an intramolecular N—H...O hydrogen bond, which generates an S(6 ring motif. In the crystal, molecules are linked by pairs of N—H...O hydrogen bonds, forming inversion dimers with an R22(12 ring motif. The dimers are linked by pairs of C—H...O hydrogen bonds, enclosing R22(6 ring motifs, forming zigzag chains along [001]. The chains are linked by a second pair of C—H...O hydrogen bonds, forming slabs parallel to (110. Within the slabs there are C—H...π interactions present. A region of disordered electron density was treated with the SQUEEZE procedure in PLATON [Spek (2015. Acta Cryst. C71, 9–18] following unsuccessful attempts to model it as plausible solvent molecule(s. The given chemical formula and other crystal data do not take into account the unknown solvent molecule(s.

  12. Schiff base: A high affinity chemical agent to decrease the concentration of aflatoxin M1 in raw milk contaminated artificially

    Directory of Open Access Journals (Sweden)

    Frane Delaš

    2012-03-01

    Full Text Available In the present study were conducted the effect of pH (5.5, 6.0 and 6.5 and concentration of new synthesized 3-/2-aminophenylimino-(p-toluoyl/-4-hydroxy-6-(p-tolyl-2H-pyrane-2-one (Schiff base on decrease the concentration of aflatoxin M1 (AFM1 in raw milk contaminated with known concentration of this toxin. Experiments were carried out at temperature of 4 °C during 35 days. At pH 5.5 Schiff base concentration of 0.1 µmol/L was lessening the concentration of AFM1 after 35 days by 55 %. However, at pH 6.5 the most effective concentration for lessening of AFM1 was 0.5 µmol/L. Schiff base was not effective at pH value of 7 or higher. The ability of Schiff base to act as antimycotoxigenic agent provides new perspective for possibly using this compound to control AFM1 contamination in milk and to extent shelf lives of this food. Detection of toxicity of investigated Schiff base was performed by using the brine shrimp (Artemia salina larvae as an biological indicator to determine their sensitivity to this chemical agent.

  13. The Study of Kinetic Properties and Analytical Pyrolysis of Coconut Shells

    Directory of Open Access Journals (Sweden)

    Mahir Said

    2015-01-01

    Full Text Available The kinetic properties of coconut shells during pyrolysis were studied to determine its reactivity in ground form. The kinetic parameters were determined by using thermogravimetric analyser. The activation energy was 122.780 kJ/mol. The pyrolysis products were analyzed using pyrolysis gas chromatography/mass spectrometry (Py-GC/MS. The effects of pyrolysis temperature on the distribution of the pyrolytic products were assessed in a temperature range between 673 K and 1073 K. The set time for pyrolysis was 2 s. Several compounds were observed; they were grouped into alkanes, acids, ethers and alcohols, esters, aldehydes and ketones, furans and pyrans, aromatic compounds, and nitrogen containing compounds. The product compositions varied with temperature in that range. The highest gas proportion was observed at high temperature while the acid proportion was observed to be highest in coconut shells, thus lowering the quality of bio-oil. It has been concluded that higher pyrolysis temperature increases the amount of pyrolysis products to a maximum value. It has been recommended to use coconut shell for production of gas, instead of production of bio-oil due to its high proportion of acetic acid.

  14. Evaluation of Extraction and Degradation Methods to Obtain Chickpeasaponin B1 from Chickpea (Cicer arietinum L.

    Directory of Open Access Journals (Sweden)

    Kun Cheng

    2017-02-01

    Full Text Available The objective of this research is to implement extraction and degradation methods for the obtainment of 3-O-[α-l-rhamnopyranosyl-(1→2-β-d-galactopyranosyl] soyasapogenol B (chickpeasaponin B1 from chickpea. The effects of microwave-assisted extraction (MAE processing parameters—such as ethanol concentration, solvent/solid ratio, extraction temperature, microwave irradiation power, and irradiation time—were evaluated. Using 1g of material with 8 mL of 70% aqueous ethanol and an extraction time of 10 min at 70 °C under irradiation power 400W provided optimal extraction conditions. Compared with the conventional extraction techniques, including heat reflux extraction (HRE, Soxhlet extraction (SE, and ultrasonic extraction (UE, MAE produced higher extraction efficiency under a lower extraction time. DDMP (2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one saponin can be degraded to structurally stable saponin B by the loss of its DDMP group. The influence of pH and the concentration of potassium hydroxide on transformation efficiency of the target compound was investigated. A solution of 0.25 M potassium hydroxide in 75% aqueous ethanol was suitable for converting the corresponding DDMP saponins of chickpeasaponin B1. The implementation by the combining MAE technique and alkaline hydrolysis method for preparing chickpeasaponin B1 provides a convenient technology for future applications.

  15. Evaluation of Extraction and Degradation Methods to Obtain Chickpeasaponin B1 from Chickpea (Cicer arietinum L.).

    Science.gov (United States)

    Cheng, Kun; Gao, Hua; Wang, Rong-Rong; Liu, Yang; Hou, Yu-Xue; Liu, Xiao-Hong; Liu, Kun; Wang, Wei

    2017-02-21

    The objective of this research is to implement extraction and degradation methods for the obtainment of 3- O -[α-l-rhamnopyranosyl-(1→2)-β-d-galactopyranosyl] soyasapogenol B (chickpeasaponin B1) from chickpea. The effects of microwave-assisted extraction (MAE) processing parameters-such as ethanol concentration, solvent/solid ratio, extraction temperature, microwave irradiation power, and irradiation time-were evaluated. Using 1g of material with 8 mL of 70% aqueous ethanol and an extraction time of 10 min at 70 °C under irradiation power 400W provided optimal extraction conditions. Compared with the conventional extraction techniques, including heat reflux extraction (HRE), Soxhlet extraction (SE), and ultrasonic extraction (UE), MAE produced higher extraction efficiency under a lower extraction time. DDMP (2,3-dihydro-2,5-dihydroxy-6-methyl-4 H -pyran-4-one) saponin can be degraded to structurally stable saponin B by the loss of its DDMP group. The influence of pH and the concentration of potassium hydroxide on transformation efficiency of the target compound was investigated. A solution of 0.25 M potassium hydroxide in 75% aqueous ethanol was suitable for converting the corresponding DDMP saponins of chickpeasaponin B1. The implementation by the combining MAE technique and alkaline hydrolysis method for preparing chickpeasaponin B1 provides a convenient technology for future applications.

  16. Prenylated flavonoids as potent phosphodiesterase-4 inhibitors from Morus alba: Isolation, modification, and structure-activity relationship study.

    Science.gov (United States)

    Guo, Yan-Qiong; Tang, Gui-Hua; Lou, Lan-Lan; Li, Wei; Zhang, Bei; Liu, Bo; Yin, Sheng

    2018-01-20

    The bioassay-guided phytochemical study of a traditional Chinese medicine Morus alba led to the isolation of 18 prenylated flavonoids (1-18), of which (±)-cyclomorusin (1/2), a pair of enantiomers, and 14-methoxy-dihydromorusin (3) are the new ones. Subsequent structural modification of the selected components by methylation, esterification, hydrogenation, and oxidative cyclization led to 14 more derivatives (19-32). The small library was screened for its inhibition against phosphodiesterase-4 (PDE4), which is a drug target for the treatment of asthma and chronic obstructive pulmonary disease (COPD). Among them, nine compounds (1-5, 8, 10, 16, and 17) exhibited remarkable activities with IC 50 values ranging from 0.0054 to 0.40 μM, being more active than the positive control rolipram (IC 50  = 0.62 μM). (+)-Cyclomorusin (1), the most active natural PDE4 inhibitor reported so far, also showed a high selectivity across other PDE members with the selective fold greater than 55. The SAR study revealed that the presence of prenyls at C-3 and/or C-8, 2H-pyran ring D, and the phenolic hydroxyl groups were important to the activity, which was further supported by the recognition mechanism study of the inhibitors with PDE4 by using molecular modeling. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

  17. Determination of the Thermodegradation of deoxyArbutin in Aqueous Solution by High Performance Liquid Chromatography

    Directory of Open Access Journals (Sweden)

    Chih-Chien Lin

    2010-10-01

    Full Text Available Tyrosinase is the key and rate-limiting enzyme responsible for the conversion of tyrosine into melanin. Competitive inhibition of tyrosinase enzymatic activity results in decreased or absent melanin synthesis by melanocytes in human skin. DeoxyArbutin (4-[(tetrahydro-2H-pyran-2-yloxy]phenol, a novel skin whitening agent, was synthesized through the removal of hydroxyl groups from the glucose side-chain of arbutin. DeoxyArbutin not only shows greater inhibition of tyrosinase activity but is also safer than hydroquinone and arbutin. Hence, deoxyArbutin is a potential skin whitening agent for cosmetics and depigmenting drugs; however, stability of this compound under some conditions remains a problem. The lack of stability poses developmental and practical difficulties for the use of deoxyArbutin in cosmetics and medicines. Improving the thermostability of deoxyArbutin is an important issue for its development. In this research, we established an analytical procedure to verify the amount of deoxyArbutin in solutions using a high performance liquid chromatographic (HPLC method. The results indicate that this novel skin whitening agent is a thermolabile compound in aqueous solutions. Additionally, the rate constant for thermodegradation (k and the half-life (t1/2 of deoxyArbutin were determined and can be used to understand the thermodegradation kinetics of deoxyArbutin. This information can aid in the application of deoxyArbutin for many future uses.

  18. Litter Quality of Populus Species as Affected by Free-Air CO2 Enrichment and N-Fertilization

    International Nuclear Information System (INIS)

    Vermue, E.; Buurman, P.; Hoosbeek, M.R.

    2010-01-01

    The effect of elevated CO 2 and nitrogen fertilization on the molecular chemistry of litter of three Populus species and associated soil organic matter (SOM) was investigated by pyrolysis-gas chromatography/mass spectrometry. The results are based on 147 quantified organic compounds in 24 litter samples. Litter of P. euramerica was clearly different from that of P. nigra and P. alba. The latter two had higher contents of proteins, polysaccharides, and cutin/cutan, while the former had higher contents of phenols and benzofurans/pyrans. The difference between replications was at least as large as the effect of treatments, so that no systematic chemical changes were attributable to CO 2 effect or N-fertilization effect. The chemistry of SOM under the various species and treatments did not show significant changes either. The low number of available replicates that is two was clearly insufficient to overcome the effect of spatial variation on litter chemistry and detect small differences in molecular litter chemistry.

  19. Litter Quality of Populus Species as Affected by Free-Air CO2 Enrichment and N-Fertilization

    Directory of Open Access Journals (Sweden)

    Esther Vermue

    2009-01-01

    Full Text Available The effect of elevated CO2 and nitrogen fertilization on the molecular chemistry of litter of three Populus species and associated soil organic matter (SOM was investigated by pyrolysis-gas chromatography/mass spectrometry. The results are based on 147 quantified organic compounds in 24 litter samples. Litter of P. euramerica was clearly different from that of P. nigra and P. alba. The latter two had higher contents of proteins, polysaccharides, and cutin/cutan, while the former had higher contents of phenols and benzofurans/pyrans. The difference between replications was at least as large as the effect of treatments, so that no systematic chemical changes were attributable to CO2 effect or N-fertilization effect. The chemistry of SOM under the various species and treatments did not show significant changes either. The low number of available replicates that is two was clearly insufficient to overcome the effect of spatial variation on litter chemistry and detect small differences in molecular litter chemistry.

  20. Synthesis of ethanol {sup 14}C-1; Synthese d'ethanol {sup 14}C-1

    Energy Technology Data Exchange (ETDEWEB)

    Wolff, R E; Pichat, L [Commissariat a l' Energie Atomique, Saclay (France). Centre d' Etudes Nucleaires

    1958-07-01

    The direct reduction by LiAlH{sub 4}, of a suspension of anhydrous sodium acetate in tetra-hydro-furfuryl-oxy-tetra-hydro-pyran is described. This study has shown that the ethanol thus obtained is impure and that the yields are erratic. On the contrary the reduction of acetyl chloride 1-{sup 14}C by LiAlH{sub 4}, in 'diethyl carbitol' leads to ethanol 1-{sup 14}C of satisfactory purity with a yield of about 71 percent. (author) [French] Une etude de la reduction directe par LiAlH{sub 4}, de l'acetate de soude anhydre en suspension dans le tetrahydrofurfuryloxytetrahydropyrane est decrite. Cette etude a montre que l'on obtient de l'ethanol souille d'impuretes, avec un rendement variable. Par contre, la reduction du chlorure d'acetyle {sup 14}C-1 par LiAlH{sub 4}, dans le 'diethyl carbitol' conduit a l'ethanol {sup 14}C-1 de purete convenable avec un rendement de l'ordre de 71 pour cent. (auteur)

  1. Sulfur-containing constituents and one 1H-pyrrole-2-carboxylic acid derivative from pineapple [Ananas comosus (L.) Merr.] fruit.

    Science.gov (United States)

    Zheng, Zong-Ping; Ma, Jinyu; Cheng, Ka-Wing; Chao, Jianfei; Zhu, Qin; Chang, Raymond Chuen-Chung; Zhao, Ming; Lin, Zhi-Xiu; Wang, Mingfu

    2010-12-01

    Two sulfur-containing compounds, (S)-2-amino-5-((R)-1-carboxy-2-((E)-3-(4-hydroxy-3-methoxyphenyl)allylthio)ethyl-amino)-5-oxopentanoic acid (1) and (S)-2-amino-5-((R)-1-(carboxymethylamino)-3-((E)-3-(4-hydroxyphenyl)allylthio)-1-oxopropan-2-ylamino)-5-oxopentanoic acid (2), and one 1H-pyrrole-2-carboxylic acid derivative, 6-(3-(1H-pyrrole-2-carbonyloxy)-2-hydroxypropoxy)-3,4,5-trihydroxy-tetrahydro-2H-pyran-2-carboxylic acid (3), together with eighteen known phenolic compounds, were isolated from the fruits of pineapple. Their structures were elucidated by a combination of spectroscopic analyses. Some of these compounds showed inhibitory activities against tyrosinase. The half maximal inhibitory concentration values of compounds 1, 4, 5, 6, 7 are lower than 1 mM. These compounds may contribute to the well-known anti-browning effect of pineapple juice and be potential skin whitening agents in cosmetic applications. Copyright © 2010 Elsevier Ltd. All rights reserved.

  2. Flupentixol tartrate.

    Science.gov (United States)

    Yamuna, Thammarse S; Kaur, Manpreet; Anderson, Brian J; Jasinski, Jerry P; Yathirajan, H S

    2014-02-01

    In the title salt, C23H26F3N2OS(+)·C4H5O6 (-) [systematic name: 1-(2-hy-droxy-eth-yl)-4-[3-(2-(tri-fluoro-meth-yl)thioxanthen-9-yl-idene)prop-yl]piperazin-1-ium 3-carb-oxy-2,3-di-hydroxy-pro-pion-ate], the monoprotonated piperazine ring in the cation adopts a chair conformation, while the thio-pyran ring of the thioxanthene group has a boat conformation. The dihedral angle between the mean planes of the two outer aromatic rings of the thioxanthene groups is 31.6 (2)°. In the crystal, the cations and anions are linked via O-H⋯O, N-H⋯O, O-H⋯N and C-H⋯O hydrogen bonds, forming chains propagating along [100]. In addition, R (2) 2(7), R (2) 2(11), R (2) 2(10) and R (2) 2(12) graph-set ring motifs involving the anions, and R (2) 2(9) graph-set ring motifs involving both the cations and anions are observed. The three F atoms of the tri-fluoro-methyl group are disordered over two sets of sites and the individual atoms were refined with occupancy ratios of 0.54 (6):0.46 (6), 0.72 (2):0.28 (2) and 0.67 (3):0.33 (3).

  3. New Cu (II), Co(II) and Ni(II) complexes of chalcone derivatives: Synthesis, X-ray crystal structure, electrochemical properties and DFT computational studies

    Science.gov (United States)

    Tabti, Salima; Djedouani, Amel; Aggoun, Djouhra; Warad, Ismail; Rahmouni, Samra; Romdhane, Samir; Fouzi, Hosni

    2018-03-01

    The reaction of nickel(II), copper(II) and cobalt(II) with 4-hydroxy-3-[(2E)-3-(1H-indol-3-yl)prop-2-enoyl]-6-methyl-2H-pyran-2-one (HL) leads to a series of new complexes: Ni(L)2(NH3), Cu(L)2(DMF)2 and Co(L)2(H2O). The crystal structure of the Cu(L)2(DMF)2 complex have been determined by X-ray diffraction methods. The Cu(II) lying on an inversion centre is coordinated to six oxygen atoms forming an octahedral elongated. Additionally, the electrochemical behavior of the metal complexes were investigated by cyclic voltammetry at a glassy carbon electrode (GC) in CH3CN solutions, showing the quasi-reversible redox process ascribed to the reduction of the MII/MI couples. The X-ray single crystal structure data of the complex was matched excellently with the optimized monomer structure of the desired compound; Hirschfeld surface analysis supported the packed crystal lattice 3D network intermolecular forces. HOMO/LUMO energy level and the global reactivity descriptors quantum parameters are also calculated. The electrophilic and nucleophilic potions in the complex surface are theoretically evaluated by molecular electrostatic potential and Mulliken atomic charges analysis.

  4. Study on electroluminescence processes in dye-doped organic light-emitting diodes

    Energy Technology Data Exchange (ETDEWEB)

    Li Weizhi [State Key Laboratory of Electronic Thin Films and Integrated devices, School of Optoelectronic Information, University of Electronic Science and Technology of China (UESTC), Chengdu 610054 (China)], E-mail: leewz@uestc.edu.cn; Jiang Yadong; Wang Tao [State Key Laboratory of Electronic Thin Films and Integrated devices, School of Optoelectronic Information, University of Electronic Science and Technology of China (UESTC), Chengdu 610054 (China)

    2008-07-15

    Electroluminescence (EL) mechanism of dye-doped organic light-emitting diodes (OLEDs) was investigated by using three familiar fluorescent dyes, i.e., 5,12-Dihydro-5,12-dimethylquino [2,3-b]acridine-7,14-dione (DMQA), 4-(dicyanomethylene)-2-t-butyl-6(1,1,7,7-tetramethyljulolidyl-9-enyl) -4H-pyran(DCJTB), and 5,6,11,12-tetraphenylnaphthacene (Rubrene). EL spectra of the doped devices with structure of indium tin oxide (ITO)/N,N'-bis-(1-naphthyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'- diamine (NPB) (40 nm)/tris-(8-hydroxyquinolate)-aluminum (Alq{sub 3}) (x nm, x=0-40 nm)/dye: Alq{sub 3} (weight ratio{approx}1%, 2 nm)/Alq{sub 3} (48-x nm)/MgAg indicated that direct carrier trapping (DCT) process dominated light emission of devices. As a result, investigation of carrier-recombination site via doping, which is conventionally applied in OLEDs, is questionable since the doping site and the dopant itself may significantly influence the carrier-recombination process in the doped devices.

  5. Influence of the substrate platform on the opto-electronic properties of multi-layer organic light-emitting field-effect transistors

    Energy Technology Data Exchange (ETDEWEB)

    Generali, Gianluca; Capelli, Raffaella; Toffanin, Stefano; Muccini, Michele [Consiglio Nazionale delle Ricerche (CNR), Istituto per lo Studio dei Materiali Nanostrutturati (ISMN), via P. Gobetti 101, I-40129 Bologna (Italy); Dinelli, Franco, E-mail: g.generali@bo.ismn.cnr.it, E-mail: m.muccini@bo.ismn.cnr.it [Consiglio Nazionale delle Ricerche (CNR), INO U.O.S. ' A. Gozzini' Area della Ricerca di Pisa - S. Cataldo, via Moruzzi 1, I-56124 Pisa (Italy)

    2011-06-08

    In this paper, we present a study of the effects of the influence of the substrate platform on the properties of a three-layer vertical hetero-junction made of thin films of {alpha}, {omega}-diperfluorohexyl-4T (DHF4T), a blend of tris(8-hydroxyquinoline)aluminium (Alq3) and 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran (DCM) and {alpha}, {omega}-dihexyl-quaterthiophene (DH4T). The hetero-junction represents the active component of an organic light-emitting transistor (OLET). The substrate platforms investigated in this study are glass/indium-tin-oxide/poly(methyl-methacrylate) (PMMA) and Si{sup ++}/silicon oxide (SiO{sub 2})/PMMA. The first platform is almost completely transparent to light and therefore is very promising for use in OLET applications. The second one has been chosen for comparison as it employs standard microelectronic materials, i.e. Si{sup ++}/SiO{sub 2}. We show how different gate materials and structure can affect the relevant field-effect electrical characteristics, such as the charge mobility and threshold voltage. By means of an atomic force microscopy analysis, a systematic study has been made in order to correlate the morphology of the active layers with the electrical properties of the devices.

  6. Red organic light emitting devices with reduced efficiency roll-off behavior by using hybrid fluorescent/phosphorescent emission structure

    Energy Technology Data Exchange (ETDEWEB)

    Zheng Tianhang; Choy, Wallace C.H., E-mail: chchoy@eee.hku.h

    2010-11-01

    Organic light emitting device (OLED) with a fluorescence-interlayer-phosphorescence emissive structure (FIP EML) is proposed to solve efficiency roll-off issue effectively. By doping fluorescent emitter of 4-(dicyanomethylene)-2-t-butyl-6-(1,1,7,7-tetramethyljulolidyl-9-enyl) -4H-pyran (DCJTB) and phosphorescent emitter of tris(1-phenylisoquinolinolato-C2,N)iridium(III) (Ir(piq){sub 3}) into the different regions of emission zone to form FIP EML in red OLED, an improvement of more than 20% in luminance efficiency roll-off compared with that of typical phosphorescent OLED with single EML in 10-500 mA/cm{sup 2} range has been obtained. Detailed mechanisms have been studied. Such improvement should be attributed to the distinct roles of the two emitters, where DCJTB mainly used to influence the carrier transport leading to an improved balance of charge carriers while Ir(piq){sub 3} functions as the radiative decay sites for most generated excitons. Meanwhile, with the help of the formation of FIP EML, the redistribution of excitons in recombination zone, the suppression of non-radiative exciton quenching processes and the elimination of energy transfer loss also contribute to the enhancement of efficiency roll-off. The method proposed here may provide a route to develop efficient OLED for high luminance applications.

  7. Comparison of the electroluminescence of a red fluorescent dye doped into the Alq{sub 3} and Alq{sub 3}:rubrene mixed host

    Energy Technology Data Exchange (ETDEWEB)

    Kang, Hee-Young; Kang, Gi-Wook; Park, Kyung-Min; Yoo, In-Sun; Lee, Changhee

    2004-01-05

    We studied the effect of a mixed host of Alq{sub 3} and rubrene on the energy transfer and charge trapping processes in organic light-emitting devices with a red fluorescent dopant of 4-(dicyanomethylene)-2-tert-butyl-6 (1,1,7,7-tetramethyljulolidyl-9-enyl)-4H-pyran (DCJTB). The temperature dependence of electroluminescence (EL) properties is compared for the device with DCJTB doped into the Alq{sub 3} only host and that with the Alq{sub 3}:rubrene mixed host. The device with the Alq{sub 3}:rubrene mixed host shows an efficient red emission from DCJTB, negligible EL emission from Alq{sub 3}, and a lower EL drive voltage compared to the device with the Alq{sub 3} only host. Upon cooling the device temperature, the EL emission from rubrene increases but the emission from Alq{sub 3} is still weak, and the quantum efficiency (QE) is almost temperature-independent for the device with the Alq{sub 3}:rubrene mixed host. On the contrary, the EL emission from Alq{sub 3} increases and the QE decreases for devices with the Alq{sub 3} only host at low temperature. The results indicate that recombination of injected electrons and holes occurs on rubrene and subsequent energy transfer to DCJTB dominates in the device with the Alq{sub 3}:rubrene mixed host.

  8. Non-doped-type white organic light-emitting diodes for lighting purpose

    Energy Technology Data Exchange (ETDEWEB)

    Zhu Jianzhuo [Key Laboratory of Excited State Processes, Changchun Institute of Optics, Fine Mechanics and Physics, Chinese Academy of Sciences, Changchun 130033 (China); Graduate School of Chinese Academy of Sciences, Beijing 100039 (China); Li Wenlian, E-mail: wllioel@yahoo.com.c [Key Laboratory of Excited State Processes, Changchun Institute of Optics, Fine Mechanics and Physics, Chinese Academy of Sciences, Changchun 130033 (China); Chu Bei, E-mail: beichu@163.co [Key Laboratory of Excited State Processes, Changchun Institute of Optics, Fine Mechanics and Physics, Chinese Academy of Sciences, Changchun 130033 (China); Yan Fei; Yang Dongfang; Liu Huihui; Wang Junbo [Key Laboratory of Excited State Processes, Changchun Institute of Optics, Fine Mechanics and Physics, Chinese Academy of Sciences, Changchun 130033 (China); Graduate School of Chinese Academy of Sciences, Beijing 100039 (China)

    2010-05-15

    We demonstrate a non-doped white organic light-emitting diode (WOLED) in which the blue-, green- and red-emissions are generated from 4,4'-bis(2,2'-diphenylvinyl)-1,1'-biphenyl, tris(8-hydroxyquinoline)aluminum (Alq) and 4-(dicyanomethylene)-2-t-butyl-6-(1,1,7,7-tetramethyl-julolidyl 9-enyl)-4H-pyran (DCJTB), which is used as an ultrathin layer. The DCJTB ultrathin layer plays the chromaticity tuning role in optimizing the white spectral band by modulating the location of the DCJTB ultrathin layer in the green emissive Alq layer. The optimized WOLED gives the Commission Internationale de l'Eclairage-1931 xy coordinates of (0.319, 0.335), a color rendering index of 91.2 at 10 V, a maximum brightness of 21010 cd/m{sup 2} at 12 V and a maximum current efficiency of 5.17 cd/A at 6.6 V. The electroluminescence mechanism of the white device is also discussed.

  9. Improved performances of red organic light-emitting devices by co-doping a rubrene derivative and DCJTB into tris-(8-hydroxyquinoline) aluminum host

    Energy Technology Data Exchange (ETDEWEB)

    Li Tianle [Physics Department, School of Science, Maoming University, Maoming 525000 (China); Key Laboratory of Excited State Processes, Changchun Institute of Optics, Fine Mechanics and Physics, Chinese Academy of Sciences, Changchun 130033 (China); Li Wenlian, E-mail: wllioel@yahoo.com.c [Key Laboratory of Excited State Processes, Changchun Institute of Optics, Fine Mechanics and Physics, Chinese Academy of Sciences, Changchun 130033 (China); Li Xiao [Key Laboratory of Excited State Processes, Changchun Institute of Optics, Fine Mechanics and Physics, Chinese Academy of Sciences, Changchun 130033 (China); Chu Bei, E-mail: beichubox@hotmail.co [Key Laboratory of Excited State Processes, Changchun Institute of Optics, Fine Mechanics and Physics, Chinese Academy of Sciences, Changchun 130033 (China); Su Zisheng; Han Liangliang; Chen Yiren [Key Laboratory of Excited State Processes, Changchun Institute of Optics, Fine Mechanics and Physics, Chinese Academy of Sciences, Changchun 130033 (China); Hu Zhizhi; Zhang Zhiqiang [Optic Photo-Electronic Materials and Research Development Center, Liaoning University of Science and Technology, Anshan 114044 (China)

    2010-10-15

    Performances of red organic light-emitting device were improved by co-doping 2-formyl-5,6,11,12-tetraphenylnaphthacene (2FRb) and 4-(dicyanomethylene)-2-t-butyl-6-(1,1,7,7-tetra-methyljulolidyl-9-enyl) -4H-pyran (DCJTB) in tris-(8-hydroxyquinoline) aluminum (Alq{sub 3}) host as the emitting layer. The device with 1 wt% DCJTB and 2.4 w% 2FRb in Alq{sub 3} host gave a saturated red emission with CIE chromaticity coordinates of (0.65, 0.35) and a maximum current efficiency as high as 6.45 cd/A, which are 2 and 2.4 fold larger than that of the device with 1 wt% DCJTB (3.28 cd/A) in Alq{sub 3} host and the device with 2.4 wt% 2FRb (2.72 cd/A) in Alq{sub 3} host at the current density of 20 mA/cm{sup 2}, respectively. The improvement could be attributed to the effective utilization of host energy by both energy transfer and trapping in the electroluminescence process and the depression of concentration quenching between the dopants molecules.

  10. Electroluminescence of organic light-emitting diodes with an ultra-thin layer of dopant

    Energy Technology Data Exchange (ETDEWEB)

    Li Weizhi [State Key Lab of Electronic Thin Films and Integrated Devices, School of Optoelectronic Information, University of Electronic Science and Technology of China (UESTC), Chengdu 610054 (China); Yu Junsheng [State Key Lab of Electronic Thin Films and Integrated Devices, School of Optoelectronic Information, University of Electronic Science and Technology of China (UESTC), Chengdu 610054 (China)], E-mail: jsyu@uestc.edu.cn; Wang, Tao [State Key Lab of Electronic Thin Films and Integrated Devices, School of Optoelectronic Information, University of Electronic Science and Technology of China (UESTC), Chengdu 610054 (China); Jiang, Yadong [State Key Lab of Electronic Thin Films and Integrated Devices, School of Optoelectronic Information, University of Electronic Science and Technology of China (UESTC), Chengdu 610054 (China)], E-mail: jiangyd@uestc.edu.cn; Wei, Bangxiong [State Key Lab of Electronic Thin Films and Integrated Devices, School of Optoelectronic Information, University of Electronic Science and Technology of China (UESTC), Chengdu 610054 (China)

    2008-03-15

    Conventional fluorescent dyes, i.e., 4-(dicyanomethylene)-2-t-butyl-6(1,1,7,7-tetramethyljulolidyl-9-enyl)-4H-pyran (DCJTB), 5,12-dihydro-5,12-dimethylquino [2,3-b]acridine-7,14-dione (DMQA) and 5,6,11,12-tetraphenylnaphthacene (Rubrene), were used to investigate the performance of organic light-emitting diodes (OLEDs) based on indium tin oxide (ITO)/N,N'-bis-(1-naphthyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine (NPB)/tris-(8-hydroxyquinolate)-aluminum (Alq{sub 3})/MgAg. The dyes were either inserted into devices as an ultra-thin film at the NPB/Alq{sub 3} interface by sequential evaporation, or doped into the Alq{sub 3} emission layer by co-evaporation with the doping ratio about 2%. Electroluminescence (EL) spectra of devices indicated that concentration quenching effect (CQE) of the dye-dopant was slightly bigger in the former than in the latter, while the degrees of CQE for three dopants are in the order of DMQA > DCJTB > Rubrene suggested by the difference in EL spectra and performances of devices. In addition, EL process of device with an ultra-thin layer of dopant is dominated by direct carrier trapping (DCT) process due to almost no holes recombine with electrons in Alq{sub 3}-host layer.

  11. Optimal thickness of hole transport layer in doped OLEDs

    Energy Technology Data Exchange (ETDEWEB)

    Zhou, Y.C.; Zhou, J.; Zhao, J.M.; Zhang, S.T.; Zhan, Y.Q.; Wang, X.Z.; Wu, Y.; Ding, X.M.; Hou, X.Y. [Fudan University, Surface Physics Laboratory (National Key Laboratory), Shanghai (China)

    2006-06-15

    Current-voltage (I-V) and electroluminescence (EL) characteristics of organic light-emitting devices with N,N'-Di-[(1-naphthalenyl)-N,N'-diphenyl]-(1,1'-biphenyl)-4,4'-diamine (NPB) of various thicknesses as the hole transport layer, and tris(8-hydroxyquinoline)aluminum (Alq{sub 3}) selectively doped with 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran (DCM) as the electron transport layer, have been investigated. A trapped charge induced band bend model is proposed to explain the I-V characteristics. It is suggested that space charge changes the injection barrier and therefore influences the electron injection process in addition to the carrier transport process. Enhanced external quantum efficiency of the devices due to the electron blocking effect of an inserted NPB layer is observed. The optimal thickness of the NPB layer is experimentally determined to be 12{+-}3 nm in doped devices, a value different from that for undoped devices, which is attributed to the electron trap effect of DCM molecules. This is consistent with the result that the proportion of Alq{sub 3} luminescence in the total electroluminescence (EL) spectra increases with NPB thickness up to 12 nm under a fixed bias. (orig.)

  12. Efficient white organic light emission by single emitting layer

    Energy Technology Data Exchange (ETDEWEB)

    Ko, Young Wook; Chung, Choong-Heui; Lee, Jin Ho; Kim, Yong-Hae; Sohn, Choong-Yong; Kim, Bong-Chul; Hwang, Chi-Sun; Song, Yoon-Ho; Lim, Jongtae; Ahn, Young-Joo; Kang, Gi-Wook; Lee, Namheon; Lee, Changhee

    2003-02-24

    Stable organic white light-emitting diodes are successfully fabricated by a single organic white emitting layer, which is Bis (2-methyl-8-quinolinato) (triphenylsiloxy) aluminum (III) (SAlq) doped red fluorescent dye of 4-(dicyanomethylene)-2-tert-butyl-6(1,1,7,7-tetramethyljulolidyl-9-enyl)- 4H-pyran (DCJTB). The incomplete energy transfer from blue-emitting SAlq to red-emitting DCJTB enables to obtain a stable white balanced light-emission by the DCJTB doping concentration of 0.5%. A device with the structure of ITO/TPD (50 nm)/SAlq:DCJTB (30 nm, 0.5%)/Alq{sub 3} (20 nm)/LiF (0.5 nm)/Al (110 nm) shows maximum luminance of 20 400 cd/m{sup 2} at 810 mA/cm{sup 2}, external quantum efficiency of 2% at 200 cd/m{sup 2} ({approx}3 mA/cm{sup 2}), power efficiency of 2.3 lm/W at 67 cd/m{sup 2} ({approx}1 mA/cm{sup 2}), and a Commission Internationale de l'Eclairage chromaticity coordinates of (0.34, 0.39) at 1.8 mA/cm{sup 2} to (0.31, 0.38) at 36 mA/cm{sup 2}.

  13. White top-emitting organic light-emitting diodes using one-emissive layer of the DCJTB doped DPVBi layer

    Energy Technology Data Exchange (ETDEWEB)

    Kim, M.S.; Jeong, C.H.; Lim, J.T. [Department of Advanced Materials Science and Engineering, Sungkyunkwan University, Suwon, Gyonggi-Do, 440-746 (Korea, Republic of); Yeom, G.Y. [Department of Advanced Materials Science and Engineering, Sungkyunkwan University, Suwon, Gyonggi-Do, 440-746 (Korea, Republic of); The National Program for Tera-level Devices, Hawolgok-dong, Sungbuk-gu, Seoul, 136-791 (Korea, Republic of)], E-mail: gyyeom@skku.edu

    2008-04-01

    White top-emitting organic light-emitting diodes (TEOLEDs) composed of one doped emissive layer which emits two-wavelength light though the radiative recombination were fabricated. As the emissive layer, 4,4-bis(2,2-diphenylethen-1-yl)biphenyl (DPVBi) was used as the host material and 4-(dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetramethyljulolidyl-9-enyl) -4H-pyran (DCJTB) was added as the dopant material. By optimizing the DCJTB concentration (1.2%) and the thickness of the DPVBi layer (30 nm), the intensity ratio of the two wavelengths could be adjusted for balanced white light emission. By using the device composed of glass/Ag (100 nm)/ITO (90 nm)/2-TNATA (60 nm)/NPB (15 nm)/DPVBi:DCJTB (1.2%, 30 nm)/Alq{sub 3} (20 nm)/Li (1.0 nm)/Al (2.0 nm)/Ag (20 nm)/ITO (63 nm)/SiO{sub 2} (42 nm), the Commission Internationale d'Eclairage (CIE) chromaticity coordinate of (0.32, 0.34) close to the ideal white color CIE coordinate could be obtained at 100 cd/m{sup 2}.

  14. The colour-tuning effect of 2,9-dimethyl-4,7-diphenyl-1, 10-phenanthroline in blue-red organic light-emitting devices

    Energy Technology Data Exchange (ETDEWEB)

    Lin Jian [Institute of Advanced Materials, Fudan University, Shanghai 200433 (China); Xia, Yi-Jie [Institute of Advanced Materials, Fudan University, Shanghai 200433 (China); Tang Chao [Institute of Advanced Materials, Nanjing University of Posts and Telecommunications (NUPT), 66 XinMoFan Road, Nanjing 210003 (China); Yin Kun [Institute of Advanced Materials, Fudan University, Shanghai 200433 (China); Zhong Gaoyu [Institute of Advanced Materials, Fudan University, Shanghai 200433 (China); Ni Gang [Institute of Advanced Materials, Fudan University, Shanghai 200433 (China); Peng Bo [Institute of Advanced Materials, Fudan University, Shanghai 200433 (China); Hou Xiaoyuan [Institute of Advanced Materials, Fudan University, Shanghai 200433 (China); Gan Fuxi [Institute of Advanced Materials, Fudan University, Shanghai 200433 (China); Huang Wei [Institute of Advanced Materials, Nanjing University of Posts and Telecommunications (NUPT), 66 XinMoFan Road, Nanjing 210003 (China)

    2007-08-07

    This paper reports the fabrication and measurement of organic light-emitting devices comprised of indium-tin-oxide (ITO)/4,4',4-prime-tris(N-carbazolyl)-triphenylamine (TCTA, 8 nm)/2-pyrenyl-9-phenyl-9-pyrenylfluorene(2P9PPF, 30 nm)/ bathocuproine (BCP, with different thickness)/Alq{sub 3} : DCJTB (DCJTB = 4-(dicyanomethylene)-2-t-butyl-6(1,1,7,7- tetramethyljulolidyl-9-enyl)-4H-pyran, Alq{sub 3} = tris(8-hydroxyquinolino) aluminium(III), 2% in mass ratio, 30 nm)/Mg : Ag(250 nm). The dependence of electroluminescence (EL) spectra on the BCP layer thickness and operating voltage has been investigated quantitatively. It is shown that the emission colour of the devices changes from red to blue at 8 V when the BCP layer thickness changes from 1 to 10 nm. The emission colour of the devices also varies with the applying voltage even in a given device. The ratio of blue emission originating from 2P9PPF to the red emission originating from DCJTB increases with the applying voltage. Based on the hole blocking effect of the BCP layer, we deduced the dependence of this ratio on the BCP layer thickness and simulated the experimental result well. It is also proposed that the variation of the EL spectrum with the voltage can be attributed to the varying hole blocking effect under the varying electric field, which resulted in a recombination zone shift, and the exciton dissociation effect in the electric field.

  15. On the origin of exciton formation in dye doped Alq{sub 3} OLEDs

    Energy Technology Data Exchange (ETDEWEB)

    Gomez, J.A. [FFCLRP-USP, Departamento de Fisica, Sao Paulo (Brazil); Castro, F.A. [National Physical Laboratory, Materials Division, Teddington (United Kingdom); Nueesch, F. [Empa, Swiss Federal Laboratories for Materials Testing and Research, Laboratory for Functional Polymers, Duebendorf (Switzerland); Zuppiroli, L. [Institut des Materiaux, EPFL, Laboratoire d' Optoelectronique des Materiaux Moleculaire, Lausanne (Switzerland); Graeff, C.F.O. [FC-UNESP, Departamento de Fisica, Sao Paulo (Brazil)

    2012-09-15

    Electrically Detected Magnetic Resonance (EDMR) was used to investigate the influence of dye doping on spin-dependent exciton formation in aluminum (III) 8-hydroxyquinoline (Alq{sub 3}) based Organic Light Emitting Diodes (OLEDs) with different device structures. 4-(dicyanomethylene)-2-methyl-6-{l_brace}2-[(4-diphenylamino)-phenyl]ethyl{r_brace}-4H-pyran (DCM-TPA) and 5,6,11,12-tetraphenylnaphthacene (Rubrene) were used as dopants. Results at room temperature show significant differences on the EDMR spectra (g-factor and linewidth) of doped and undoped devices. Signals from DCM-TPA and Rubrene dye doped OLEDs showed strong temperature dependence, with signal intensity increasing by 2 orders of magnitude below 200 K for DCM-TPA dye doped OLEDs and increasing by {proportional_to}1 order of magnitude below 225 K for the Rubrene dye doped device, while undoped devices shows almost no temperature dependence. By adding a ''spacer'' layer of undoped Alq{sub 3} at the recombination zone, changes in bias voltage were used to shift the recombination from doped to undoped region and correlate that with changes in the EDMR spectrum. Our results are indicating that charge trapping on the dopant followed by recombination is the main mechanism of light emission in the investigated devices. (orig.)

  16. Design of new metal-free dyes for dye-sensitized solar cells: A first-principles study

    Energy Technology Data Exchange (ETDEWEB)

    Gu, Xiong; Zhou, Le; Li, Yawei [Department of Materials Science and Engineering, College of Engineering, Peking University, Beijing 100871 (China); Sun, Qiang, E-mail: sunqiang@pku.edu.cn [Department of Materials Science and Engineering, College of Engineering, Peking University, Beijing 100871 (China); Center for Applied Physics and Technology, Peking University, Beijing 100871 (China); Jena, Puru [Department of Physics, Virginia Commonwealth University, Richmond, VA 23284 (United States)

    2012-08-06

    Five new metal-free dyes with acceptor–π–donor (A–π–D) structure are studied using first-principles calculation based on density functional theory. Benzothiadiazole (BTD) and triphenylamine (TPA) were chosen, respectively, as an acceptor and a donor with 4-(dicyanomethylene)-2-methyl-6-(4-dimethylamino-styryl)-4H-pyran (DCM) as a π linker. The linker was further modified by -CH=CH- resulting in a red-shift with improved absorption spectra caused by the smaller energy gap and the increased orbital hybridization. The designed dyes are found to exhibit wide absorption spectra, high molar extinction coefficients, desirable orbital distributions, and good energy levels alignment, and hence can have potential applications in dye-sensitized solar cells. -- Highlights: ► New metal-free dyes with A–π–D architecture. ► With wide absorption spectra and high molar extinction coefficients. ► With desirable orbital distribution and good energy levels alignment.

  17. White organic light emitting diodes based on DCM dye sandwiched in 2-methyl-8-hydroxyquinolinolatolithium

    Energy Technology Data Exchange (ETDEWEB)

    Kumar, Amit [Center for Organic Electronics, Polymeric and Soft Materials Section, National Physical Laboratory (Council of Scientific and Industrial Research), Dr. K.S. Krishnan Road, New Delhi 110012 (India); Department of Chemistry, M.D. University, Rohtak, Haryana 124001 (India); Srivastava, Ritu, E-mail: ritu@mail.nplindia.ernet.i [Center for Organic Electronics, Polymeric and Soft Materials Section, National Physical Laboratory (Council of Scientific and Industrial Research), Dr. K.S. Krishnan Road, New Delhi 110012 (India); Bawa, Sukhwant S. [Center for Organic Electronics, Polymeric and Soft Materials Section, National Physical Laboratory (Council of Scientific and Industrial Research), Dr. K.S. Krishnan Road, New Delhi 110012 (India); Singh, Devender; Singh, Kapoor [Department of Chemistry, M.D. University, Rohtak, Haryana 124001 (India); Chauhan, Gayatri [Center for Organic Electronics, Polymeric and Soft Materials Section, National Physical Laboratory (Council of Scientific and Industrial Research), Dr. K.S. Krishnan Road, New Delhi 110012 (India); Singh, Ishwar [Department of Chemistry, M.D. University, Rohtak, Haryana 124001 (India); Kamalasanan, Modeeparampil N. [Center for Organic Electronics, Polymeric and Soft Materials Section, National Physical Laboratory (Council of Scientific and Industrial Research), Dr. K.S. Krishnan Road, New Delhi 110012 (India)

    2010-08-15

    Stable white electroluminescence (EL) has been achieved from organic LED, in which an ultrathin 4-(dicyanomethylene)-2-methyl-6-(p-dimethyl-aminostyryl)-4H-pyran (DCM) dye layer has been inserted in between two 2-methyl-8-hydroxyquinolinolatolithium [LiMeq] emitter layer and by optimizing the position of the DCM dye layer from the {alpha}-NPD/LiMeq interface. Electroluminescence spectra, current-voltage-luminescence (I-V-L) characteristics of the devices have been studied by changing the position of the dye layer. As the distance of DCM layer from {alpha}-NPD/LiMeq interface is increased, the intensity of host emission enhances rapidly. Introduction of thin layer of DCM in emissive layer increases the turn on voltage. The best Commission International de L' Eclairage (CIE) coordinates i.e. (0.32, 0.33) were obtained with device structure ITO/{alpha}-NPD(30 nm) /LiMeq(10 nm)/DCM(1 nm)/LiMeq(25 nm)/BCP(6 nm)/Alq{sub 3}(28 nm)/LiF(1 nm)/Al(100 nm). The EL spectrum covers the whole visible spectra range 400-700 nm. The color rendering index (CRI) for our best white light (Device 4) is 47.4. The device shows very good color stability in terms of CIE coordinates with voltages. The maximum luminescence 1240 cd/m{sup -2} has been achieved at 19 V.

  18. 6-Chloro-7-fluoro-4-oxo-4H-chromene-3-carbaldehyde

    Directory of Open Access Journals (Sweden)

    Yoshinobu Ishikawa

    2014-07-01

    Full Text Available In the title compound, C10H4ClFO3, a chlorinated and fluorinated 3-formylchromone derivative, all atoms are essentially coplanar (r.m.s. = 0.0336 Å for the non-H atoms, with the largest deviation from the least-squares plane [0.062 (2 Å] being for a benzene-ring C atom. In the crystal, molecules are linked through stacking interactions [centroid–centroid distance between the benzene and pyran rings = 3.958 (3 Å and interplanar distance = 3.259 (3 Å], C—H...O hydrogen bonds, and short C...O contacts [2.879 (3 Å]. Unsymmetrical halogen–halogen interactions between the Cl and F atoms [Cl...F = 3.049 (3 Å, C—Cl...F = 148.10 (9° and C—F...Cl = 162.06 (13°] are also formed, giving a meandering two-dimensional network along the a axis.

  19. White organic light-emitting devices with tunable color emission fabricated utilizing exciplex formation at heterointerfaces including m-MDATA

    International Nuclear Information System (INIS)

    Lee, Kwang Seop; Choo, Dong Chul; Kim, Tae Whan

    2011-01-01

    The electrical and the optical properties of organic light-emitting devices (OLEDs) fabricated utilizing a 4,4',4''-tris(2-methylphenyl-phenylamino)triphenylamine (m-MTDATA) were investigated to clarify the effect of exciplex on their color stabilization and color purity. The electrons combined with the holes at heterointerfaces between the m-MTDATA layer and the 9,10-di(2-naphthyl)anthracene (MADN) and the 4-(dicyanomethylene)-2-methyl-6-(p-dimethyl aminostyryl)-4H-pyran (DCM1) emitting layer (EML) resulted in the formation of the exciplex. The emission peak of the electroluminescence spectra for the OLEDs fabricated utilizing the m-MTDATA layer shifted to a lower energy side in comparison with that of the EML. This was due to the interaction of the holes in the m-MTDATA layer and the electrons in the MADN EML. Carriers in white OLEDs (WOLEDs) with exciplex emissions existed at the heterointerfaces between the m-MTDATA and the EML because the DCM1 EML was too thin to affect the EL peak related to the m-MTDATA layer. The Commission Internationale de l'Eclairage coordinates of WOLEDs at 9.5 V were (0.33, 0.36), and their maximum current efficiency at 46 mA/cm 2 was 2.03 cd/A.

  20. White organic light-emitting devices with tunable color emission fabricated utilizing exciplex formation at heterointerfaces including m-MDATA

    Energy Technology Data Exchange (ETDEWEB)

    Lee, Kwang Seop; Choo, Dong Chul; Kim, Tae Whan, E-mail: twk@hanyang.ac.kr

    2011-05-31

    The electrical and the optical properties of organic light-emitting devices (OLEDs) fabricated utilizing a 4,4',4''-tris(2-methylphenyl-phenylamino)triphenylamine (m-MTDATA) were investigated to clarify the effect of exciplex on their color stabilization and color purity. The electrons combined with the holes at heterointerfaces between the m-MTDATA layer and the 9,10-di(2-naphthyl)anthracene (MADN) and the 4-(dicyanomethylene)-2-methyl-6-(p-dimethyl aminostyryl)-4H-pyran (DCM1) emitting layer (EML) resulted in the formation of the exciplex. The emission peak of the electroluminescence spectra for the OLEDs fabricated utilizing the m-MTDATA layer shifted to a lower energy side in comparison with that of the EML. This was due to the interaction of the holes in the m-MTDATA layer and the electrons in the MADN EML. Carriers in white OLEDs (WOLEDs) with exciplex emissions existed at the heterointerfaces between the m-MTDATA and the EML because the DCM1 EML was too thin to affect the EL peak related to the m-MTDATA layer. The Commission Internationale de l'Eclairage coordinates of WOLEDs at 9.5 V were (0.33, 0.36), and their maximum current efficiency at 46 mA/cm{sup 2} was 2.03 cd/A.

  1. PET imaging of T cells: Target identification and feasibility assessment.

    Science.gov (United States)

    Auberson, Yves P; Briard, Emmanuelle; Rudolph, Bettina; Kaupmann, Klemen; Smith, Paul; Oberhauser, Berndt

    2018-06-01

    Imaging T cells using positron emission tomography (PET) would be highly useful for diagnosis and monitoring in immunology and oncology patients. There are however no obvious targets that can be used to develop imaging agents for this purpose. We evaluated several potential target proteins with selective expression in T cells, and for which lead molecules were available: PKC , Lck, ZAP70 and Itk. Ultimately, we focused on Itk (interleukin-2-inducible T cell kinase) and identified a tool molecule with properties suitable for in vivo imaging of T cells, (5aR)-5,5-difluoro-5a-methyl-N-(1-((S)-3-(methylsulfonyl)-phenyl)(tetrahydro-2H-pyran-4-yl)methyl)-1H-pyrazol-4-yl)-1,4,4a,5,5a,6-hexahydro-cyclopropa[f]-indazole-3-carboxamide (23). While not having the optimal profile for clinical use, this molecule indicates that it might be possible to develop Itk-selective PET ligands for imaging the distribution of T cells in patients. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  2. Visual detection and sequential injection determination of aluminium using a cinnamoyl derivative.

    Science.gov (United States)

    Elečková, Lenka; Alexovič, Michal; Kuchár, Juraj; Balogh, Ioseph S; Andruch, Vasil

    2015-02-01

    A cinnamoyl derivative, 3-[4-(dimethylamino)cinnamoyl]-4-hydroxy-6-methyl-3,4-2H-pyran-2-one, was used as a ligand for the determination of aluminium. Upon the addition of an acetonitrile solution of the ligand to an aqueous solution containing Al(III) and a buffer solution at pH 8, a marked change in colour from yellow to orange is observed. The colour intensity is proportional to the concentration of Al(III); thus, the 'naked-eye' detection of aluminium is possible. The reaction is also applied for sequential injection determination of aluminium. Beer׳s law is obeyed in the range from 0.055 to 0.66 mg L(-1) of Al(III). The limit of detection, calculated as three times the standard deviation of the blank test (n=10), was found to be 4 μg L(-1) for Al(III). The method was applied for the determination of aluminium in spiked water samples and pharmaceutical preparations. Copyright © 2014 Elsevier B.V. All rights reserved.

  3. Supplementary data for the mechanism for cleavage of three typical glucosidic bonds induced by hydroxyl free radical

    Directory of Open Access Journals (Sweden)

    Yujie Dai

    2017-12-01

    Full Text Available The data presented in this article are related to the research article entitled “The mechanism for cleavage of three typical glucosidic bonds induced by hydroxyl free radical” (Dai et al., 2017 [1]. This article includes the structures of three kinds of disaccharides such as maltose, fructose and cellobiose, the diagrammatic sketch of the hydrogen abstraction reaction of the disaccharides by hydroxyl radical, the structure of the transition states for pyran ring opening of moiety A and cleavage of α(1→2 glycosidic bond starting from the hydrogen abstraction of C6–H in moiety A of sucrose, the transition state structure for cleavage of α(1→2 glycosidic bond starting from the hydrogen abstraction of C1′-H in moiety B of sucrose, the transition state structure, sketch for the reaction process and relative energy change of the reaction pathway for direct cleavage of α(1→4 glycosidic bond starting from hydrogen abstraction of C6′–H of moiety B of maltose.

  4. Design and synthesis of new fluorescent probe for rapid and highly sensitive detection of proteins via electrophoretic gel stain.

    Science.gov (United States)

    Suzuki, Yoshio; Takagi, Nobuyuki; Chimuro, Tomoyuki; Shinohara, Atsushi; Sakaguchi, Nao; Hiratsuka, Atsunori; Yokoyama, Kenji

    2011-06-01

    A new fluorescent molecular probe, 2,2'-(1E,1'E)-2,2'-(4-(dicyanomethylene)-4H-pyrane-2,6-diyl)bis(ethene-2,1-diyl)bis(sodium benzenesulfonate) salt (1), possessing the cyanopyranyl moieties and two benzene sulfonic acid groups was designed and synthesized to detect proteins in solution and for high-throughput SDS-PAGE. Compound 1 exhibited no fluorescence in the absence of proteins; however, it exhibited strong fluorescence on the addition of bovine serum albumin as a result of intramolecular charge transfer. Compared with the conventional protocols for in-gel protein staining, such as SYPRO Ruby and silver staining, 1 achieves higher sensitivity, even though it offers a simplified, higher throughput protocol. In fact, the total time required for protein staining was 60-90 min under optimum conditions much shorter than that required by the less-sensitive silver staining or SYPRO Ruby staining protocols. Moreover, 1 was successfully applied to protein identification by mass spectrometry via in-gel tryptic digestion, Western blotting, and native PAGE together with protein staining by 1, which is a modified protocol of blue native PAGE (BN-PAGE). Thus, 1 may facilitate high-sensitivity protein detection, and it may be widely applicable as a convenient tool in various scientific and medical fields. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  5. Produtos naturais da ascídia Botrylloides giganteum, das esponjas Verongula gigantea, Ircinia felix, Cliona delitrix e do nudibrânquio Tambja eliora, da costa do Brasil Natural products from the ascidian Botrylloides giganteum, from the sponges Verongula gigantea, Ircinia felix, Cliona delitrix and from the nudibranch Tambja eliora, from the Brazilian coastline

    Directory of Open Access Journals (Sweden)

    Ana Claudia Granato

    2005-03-01

    Full Text Available Two new marine metabolites, 3Z, 6Z, 9Z-dodecatrien-1-ol (1 from the ascidian Botrylloides giganteum and 4H-pyran-2ol acetate from the sponge Ircinia felix (4 are herein reported. The known bromotyrosine compounds, 2-(3,5-dibromo-4-methoxyphenyl-N,N,N-dimethylethanammonium (2 and 2,6-dibromo-4-(2-(trimethylammoniumethylphenol (3, have been isolated from the sponge Verongula gigantea. Serotonin (5 is reported for the first time from the sponge Cliona delitrix, and tambjamines A (15 and D (16 isolated as their respective salts from the nudibranch Tambja eliora. Only tambjamine D presented cytotoxicity against CEM (IC50 12.2 µg/mL and HL60 (IC50 13.2 µg/mL human leukemya cells, MCF-7 breast cancer cells (IC50 13.2 µg/mL, colon HCT-8 cancer cells (IC50 10.1 µg/mL and murine melanoma B16 cancer cells (IC50 6.7 µg/mL.

  6. Cytotoxic and Antifungal Constituents Isolated from the Metabolites of Endophytic Fungus DO14 from Dendrobium officinale

    Directory of Open Access Journals (Sweden)

    Ling-Shang Wu

    2015-12-01

    Full Text Available Two novel cytotoxic and antifungal constituents, (4S,6S-6-[(1S,2R-1, 2-dihydroxybutyl]-4-hydroxy-4-methoxytetrahydro-2H-pyran-2-one (1, (6S,2E-6-hydroxy-3-methoxy-5-oxodec-2-enoic acid (2, together with three known compounds, LL-P880γ (3, LL-P880α (4, and Ergosta-5,7,22-trien-3b-ol (5 were isolated from the metabolites of endophytic fungi from Dendrobium officinale. The chemical structures were determined based on spectroscopic methods. All the isolated compounds 1–5 were evaluated by cytotoxicity and antifungal effects. Our present results indicated that compounds 1–4 showed notable anti-fungal activities (minimal inhibitory concentration (MIC ≤ 50 μg/mL for all the tested pathogens including Candida albicans, Cryptococcus neoformans, Trichophyton rubrum, Aspergillus fumigatus. In addition, compounds 1–4 possessed notable cytotoxcities against human cancer cell lines of HL-60 cells with the IC50 values of below 100 μM. Besides, compounds 1, 2, 4 and 5 showed strong cytotoxities on the LOVO cell line with the IC50 values were lower than 100 μM. In conclusion, our study suggested that endophytic fungi of D. officinale are great potential resources to discover novel agents for preventing or treating pathogens and tumors.

  7. Cytotoxic and Antifungal Constituents Isolated from the Metabolites of Endophytic Fungus DO14 from Dendrobium officinale.

    Science.gov (United States)

    Wu, Ling-Shang; Jia, Min; Chen, Ling; Zhu, Bo; Dong, Hong-Xiu; Si, Jin-Ping; Peng, Wei; Han, Ting

    2015-12-22

    Two novel cytotoxic and antifungal constituents, (4S,6S)-6-[(1S,2R)-1, 2-dihydroxybutyl]-4-hydroxy-4-methoxytetrahydro-2H-pyran-2-one (1), (6S,2E)-6-hydroxy-3-methoxy-5-oxodec-2-enoic acid (2), together with three known compounds, LL-P880γ (3), LL-P880α (4), and Ergosta-5,7,22-trien-3b-ol (5) were isolated from the metabolites of endophytic fungi from Dendrobium officinale. The chemical structures were determined based on spectroscopic methods. All the isolated compounds 1-5 were evaluated by cytotoxicity and antifungal effects. Our present results indicated that compounds 1-4 showed notable anti-fungal activities (minimal inhibitory concentration (MIC) ≤ 50 μg/mL) for all the tested pathogens including Candida albicans, Cryptococcus neoformans, Trichophyton rubrum, Aspergillus fumigatus. In addition, compounds 1-4 possessed notable cytotoxcities against human cancer cell lines of HL-60 cells with the IC50 values of below 100 μM. Besides, compounds 1, 2, 4 and 5 showed strong cytotoxities on the LOVO cell line with the IC50 values were lower than 100 μM. In conclusion, our study suggested that endophytic fungi of D. officinale are great potential resources to discover novel agents for preventing or treating pathogens and tumors.

  8. Exploration of flexible phenylpropylurea scaffold as novel cardiac myosin activators for the treatment of systolic heart failure.

    Science.gov (United States)

    Manickam, Manoj; Jalani, Hitesh B; Pillaiyar, Thanigaimalai; Sharma, Niti; Boggu, Pulla Reddy; Venkateswararao, Eeda; Lee, You-Jung; Jeon, Eun-Seok; Jung, Sang-Hun

    2017-07-07

    A series of flexible urea derivatives have been synthesized and demonstrated as selective cardiac myosin ATPase activator. Among them 1-phenethyl-3-(3-phenylpropyl)urea (1, cardiac myosin ATPase activation at 10 μM = 51.1%; FS = 18.90; EF = 12.15) and 1-benzyl-3-(3-phenylpropyl)urea (9, cardiac myosin ATPase activation = 53.3%; FS = 30.04; EF = 18.27) showed significant activity in vitro and in vivo. The change of phenyl ring with tetrahydropyran-4-yl moiety viz., 1-(3-phenylpropyl)-3-((tetrahydro-2H-pyran-4-yl)methyl)urea (14, cardiac myosin ATPase activation = 81.4%; FS = 20.50; EF = 13.10), and morpholine moiety viz., 1-(2-morpholinoethyl)-3-(3-phenylpropyl)urea (21, cardiac myosin ATPase activation = 44.0%; FS = 24.79; EF = 15.65), proved to be efficient to activate the cardiac myosin. The potent compounds 1, 9, 14 and 21 were found to be selective for cardiac myosin over skeletal and smooth myosins. Thus, these urea derivatives are potent scaffold to develop as a newer cardiac myosin activator for the treatment of systolic heart failure. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

  9. Natural products from the ascidian Botrylloides giganteum, from the sponges Verongula gigantea, Ircinia felix, Cliona delitrix and from the nudibranch Tambja eliora, from the Brazilian coastline; Produtos naturais da ascidia Botrylloides giganteum, das esponjas Verongula gigantea, Ircinia felix, Cliona delitrix e do nudibranquio Tambja eliora, da costa do Brasil

    Energy Technology Data Exchange (ETDEWEB)

    Granato, Ana Claudia; Oliveira, Jaine H.H.L. de; Seleghim, Mirna H.R.; Berlinck, Roberto G.S. [Sao Paulo Univ., Sao Carlos, SP (Brazil). Inst. de Quimica]. E-mail: rgsberlinck@iqsc.usp.br; Macedo, Mario L.; Ferreira, Antonio G. [Sao Carlos Univ., SP (Brazil). Dept. de Quimica; Rocha, Rosana M. da [Parana Univ., Curitiba, PR (Brazil). Setor de Ciencias Biologicas. Dept. de Zoologia; Hajdu, Eduardo [Universidade Federal, Rio de Janeiro, RJ (Brazil). Museu Nacional; Peixinho, Solange [Bahia Univ., Salvador, BA (Brazil). Dept. de Biologia; Pessoa, Claudia O.; Moraes, Manoel O.; Cavalcanti, Bruno C. [Ceara Univ., Fortaleza, CE (Brazil). Dept. de Fisiologia e Farmacologia

    2005-04-01

    Two new marine metabolites, 3Z, 6Z, 9Z-dodecatrien-1-ol (1) from the ascidian Botrylloides giganteum and 4H-pyran-2ol acetate from the sponge Ircinia felix (4) are herein reported. The known bromotyrosine compounds, 2-(3,5-dibromo-4-methoxyphenyl)-N,N,Ndimethylethanammonium (2) and 2,6-dibromo-4-(2-(trimethylammonium)ethyl)phenol (3), have been isolated from the sponge Verongula gigantea. Serotonin (5) is reported for the first time from the sponge Cliona delitrix, and tambjamines A (15) and D (16) isolated as their respective salts from the nudibranch Tambja eliora. Only tambjamine D presented cytotoxicity against CEM (IC{sub 5})0 12.2 {mu}g/mL) and HL60 (IC{sub 50} 13.2 {mu}g/mL) human leukemia cells, MCF-7 breast cancer cells (IC{sub 50} 13.2 {mu}g/mL), colon HCT-8 cancer cells (IC{sub 50} 10.1 {mu}g/mL) and murine melanoma B16 cancer cells (IC{sub 50} 6.7 {mu}g/mL). (author)

  10. High color rendering index white organic light-emitting diode using levofloxacin as blue emitter

    International Nuclear Information System (INIS)

    Miao Yan-Qin; Zhang Ai-Qin; Li Yuan-Hao; Wang Hua; Jia Hu-Sheng; Liu Xu-Guang; Gao Zhi-Xiang; Tsuboi Taijuf

    2015-01-01

    Levofloxacin (LOFX), which is well-known as an antibiotic medicament, was shown to be useful as a 452-nm blue emitter for white organic light-emitting diodes (OLEDs). In this paper, the fabricated white OLED contains a 452-nm blue emitting layer (thickness of 30 nm) with 1 wt% LOFX doped in CBP (4,4’-bis(carbazol-9-yl)biphenyl) host and a 584-nm orange emitting layer (thickness of 10 nm) with 0.8 wt% DCJTB (4-(dicyanomethylene)-2-tert-butyl-6-(1,1,7, 7-tetramethyljulolidin-4-yl-vinyl)-4H-pyran) doped in CBP, which are separated by a 20-nm-thick buffer layer of TPBi (2,2’,2”-(benzene-1,3,5-triyl)-tri(1-phenyl-1H-benzimidazole). A high color rendering index (CRI) of 84.5 and CIE chromaticity coordinates of (0.33, 0.32), which is close to ideal white emission CIE (0.333, 0.333), are obtained at a bias voltage of 14 V. Taking into account that LOFX is less expensive and the synthesis and purification technologies of LOFX are mature, these results indicate that blue fluorescence emitting LOFX is useful for applications to white OLEDs although the maximum current efficiency and luminance are not high. The present paper is expected to become a milestone to using medical drug materials for OLEDs. (paper)

  11. High-efficient and brightness white organic light-emitting diodes operated at low bias voltage

    Science.gov (United States)

    Zhang, Lei; Yu, Junsheng; Yuan, Kai; Jian, Yadong

    2010-10-01

    White organic light-emitting diodes (OLEDs) used for display application and lighting need to possess high efficiency, high brightness, and low driving voltage. In this work, white OLEDs consisted of ambipolar 9,10-bis 2-naphthyl anthracene (ADN) as a host of blue light-emitting layer (EML) doped with tetrabutyleperlene (TBPe) and a thin codoped layer consisted of N, N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)-benzidine (NPB) as a host of yellow light-emitting layer doped with 4-(dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetramethyljulolidin-4-yl-vinyl)-4H-pyran (DCJTB) were investigated. With appropriate tuning in the film thickness, position, and dopant concentration of the co-doped layer, a white OLED with a luminance yield of 10.02 cd/A with the CIE coordinates of (0.29, 0.33) has been achieved at a bias voltage of 9 V and a luminance level of over 10,000 cd/m2. By introducing the PIN structure with both HIL and bis(10- hydroxybenzo-quinolinato)-beryllium (BeBq2) ETL, the power efficiency of white OLED was improved.

  12. Improvement of color purity in white OLED based on Zn(HPB){sub 2} as blue emitting layer

    Energy Technology Data Exchange (ETDEWEB)

    Kim, Dong-Eun [Department of Electrical Engineering and NTRC, Dong-A University, Busan, 604-714 (Korea, Republic of); Kim, Won-Sam [Department of Chemistry and Institute of Functional Materials, Inje University, Gimhae, 621-749 (Korea, Republic of); Kim, Byoung-Sang [Department of Electrical Engineering and NTRC, Dong-A University, Busan, 604-714 (Korea, Republic of); Lee, Burm-Jong [Department of Chemistry and Institute of Functional Materials, Inje University, Gimhae, 621-749 (Korea, Republic of); Kwon, Young-Soo [Department of Electrical Engineering and NTRC, Dong-A University, Busan, 604-714 (Korea, Republic of)], E-mail: yskwon@dau.ac.kr

    2008-04-01

    We synthesized zinc (II) [2-(2-hydroxyphenyl)benzoxazole] (Zn(HPB){sub 2}) as blue emitting materials and evaluated in the organic light emitting diodes (OLEDs). The layer of Zn(HPB){sub 2} doped with 4-(dicyanomethylene)-2-t-butyl-6(1,1,7,7-tetramethyljulolidyl-9-enyl) -4H-pyran (DCJTB) (Zn(HPB){sub 2}:DCJTB) as emitters has been demonstrated. The structure of the device is indium-tin-oxide (ITO)/N,N'-bis-(1-naphthl)-diphenyl-1,1'-biphenyl-4,4'-diamine (NPB, 40 nm)/Zn(HPB){sub 2}/Zn(HPB){sub 2}:DCJTB/Alq{sub 3} (20 nm)/LiF/Al. The thickness of Zn(HPB){sub 2} layer was 0, 10, 20, 30 nm at the same time the thickness of Zn(HPB){sub 2}:DCJTB layer were 40, 30, 20, 10 nm. When thickness of Zn(HPB){sub 2} layer was 30 nm and the thickness of Zn(HPB){sub 2}:DCJTB layer was 10 nm, white emission is achieved. The Commission Internationale de l'Eclairage (CIE) coordinates of the white emission are (0.304, 0.332) at an applied voltage of 10.5 V.

  13. Structural basis of malaria parasite lysyl-tRNA synthetase inhibition by cladosporin.

    Science.gov (United States)

    Khan, Sameena; Sharma, Arvind; Belrhali, Hassan; Yogavel, Manickam; Sharma, Amit

    2014-06-01

    Malaria parasites inevitably develop drug resistance to anti-malarials over time. Hence the immediacy for discovering new chemical scaffolds to include in combination malaria drug therapy. The desirable attributes of new chemotherapeutic agents currently include activity against both liver and blood stage malaria parasites. One such recently discovered compound called cladosporin abrogates parasite growth via inhibition of Plasmodium falciparum lysyl-tRNA synthetase (PfKRS), an enzyme central to protein translation. Here, we present crystal structure of ternary PfKRS-lysine-cladosporin (PfKRS-K-C) complex that reveals cladosporin's remarkable ability to mimic the natural substrate adenosine and thereby colonize PfKRS active site. The isocoumarin fragment of cladosporin sandwiches between critical adenine-recognizing residues while its pyran ring fits snugly in the ribose-recognizing cavity. PfKRS-K-C structure highlights ample space within PfKRS active site for further chemical derivatization of cladosporin. Such derivatives may be useful against additional human pathogens that retain high conservation in cladosporin chelating residues within their lysyl-tRNA synthetase.

  14. Modification of radiation effects

    International Nuclear Information System (INIS)

    Lindenbaum, A.

    1975-01-01

    Results are reported from studies on the tissue distribution of 239 Pu and 241 Am in mice and beagle dogs and the effectiveness of various therapeutic treatments for decorporation. In dogs injected with monomeric Pu the value of a regimen of early and prolonged treatment with DTPA (diethylenetriaminepentaacetic acid) for minimizing the Pu burden in the soft tissues and skeleton was demonstrated. These results have immediate implication for DTPA treatment in man. New studies in mice verified the action of pyran copolymer antiviral agents in enhancing the effectiveness of DTPA for removal of polymeric Pu from the liver. Recent application of autoradiographic procedures for quantitatively comparing short- and long-term localization of monomeric and polymeric 239 Pu in dog liver showed that there is no net translocation of monomeric Pu within the liver between 6 and 90 days following injection. One of the molecular studies presently underway aims at synthesis of a variety of DTPA esters. The diethyl ester has already been prepared and tested for toxicity in mice. These compounds are designed to bring DTPA into contact with plutonium deposits unavailable to the action of ionic DTPA. (U.S.)

  15. (4′-Acetyloxy-1,3,1′-trioxo-1,3,4,4a,4b,5,6,7,9,9a-decahydrospiro[indene-2,9′-pyrano[4,3-a]pyrrolizin]-3′-ylmethyl acetate

    Directory of Open Access Journals (Sweden)

    S. Lakshmi

    2013-12-01

    Full Text Available In the title compound, C23H23NO8, the dihedral angle between the five- and six-membered rings of the indene-dione moiety is 3.09 (13°. The mean plane of the five-membered ring (which has a flat envelope conformation with the spiro C atom as the flap is inclined to the mean plane of the central five-membered ring of the pyrrolizine unit by 76.48 (12°. This central ring has a twist conformation on the N—C(spiro bond. The outer ring of the pyrrolizine unit has an envelope conformation with the N atom as the flap. The mean planes of these two fused rings are inclined to one another by 65.28 (15°. The pyran ring has a screw-boat conformation and its mean plane makes a dihedral angle of 29.50 (11° with the mean plane of the central five-membered ring of the pyrrolizine unit. In the crystal, molecules are linked via C—H...O hydrogen bonds, forming two-dimensional networks lying parallel to the ab plane.

  16. Synthesis, structural characterization, electrochemical and biological studies on divalent metal chelates of a new ligand derived from pharmaceutical preservative, dehydroacetic acid, with 1,4-diaminobenzene

    Directory of Open Access Journals (Sweden)

    Sanaa M. Emam

    2017-05-01

    Full Text Available Cobalt(II, nickel(II, copper(II, zinc(II and cadmium(II complexes of new 3-acetyl-4-[(4-aminophenylamino]-6-methyl-2H-pyran-2-one (HL1 derived from dehydroacetic acid and 1,4-diaminobenzene were prepared and characterized. The structural features were determined from their elemental analyses, 1H, and 13C-NMR spectra, molar conductivities, magnetic moments, IR, UVvis. spectra, thermal analyses (D.T.A. and T.G.A. and E.S.R. measurements. Their magnetic susceptibility measurements and low conductance data provide evidence for the mono- or dimeric and non-electrolytic nature of the solid complexes. The E.S.R. spectra of copper(II complexes show axial type symmetry with covalent or ionic bond character. The electrochemical behavior of the complexes in DMF (dimethylformamide solvent at 298 K was studied. The biological activity of the ligand and its metal(II complexes was also studied. The obtained complexes showed higher activities than the free ligand in protecting the Egyptian cotton fields from Spodoptera littoralis larvae.

  17. Essential oil composition, antioxidant and antifungal activities of Salvia sclarea L. from Munzur Valley in Tunceli, Turkey.

    Science.gov (United States)

    Yuce, E; Yildirim, N; Yildirim, N C; Paksoy, M Y; Bagci, E

    2014-06-15

    The essential oil composition and in vitro antioxidant and antifungal activity of the Salvia sclarea L. from Munzur Valley in Tunceli, Turkey were evaluated in this research. The in vitro antifungal activity of ethanol, hexane and aqueous extracts of S. sclarea against pathogen fungi Epicoccum nigrum and Colletotrichum coccodes were investigated. The essential oil of aerial parts of S. sclarea was obtained by hydrodistillation and was analysed by GC and GC—MS. Total antioxidant status was determined by using Rel assay diagnostics TAS assay kit (Lot.RL024) by Multiscan FC (Thermo). 33 compounds were identified representing the 85.0% of the total oil. The most abundant components (>5%) of the S. sclarea essential oils were caryophyllene oxide (24.1%), sclareol (11.5%), spathulenol (11.4%), 1H-naphtho (2,1,6) pyran (8.6%) and b—caryophyllene (5.1%). The best antifungal and antioxidant effect was seen in ethanolic S. sclarea extract. It can be said that Salvia sclerae could be used as natural antioxidant.

  18. Zinc Enolate/Sulfinate Prepared from a Single-Run Reaction Using Zinc Dust with O-Tosylated 4-Hydroxy Coumarin and Pyrone

    International Nuclear Information System (INIS)

    Shin, Ueon Sang; Joo, Seong-Ryu; Kim, Seung-Hoi

    2016-01-01

    We demonstrated the preparation of new zinc complexes, 2-oxo-2H-chromen-4-yloxy tosylzinc (I), and 6-methyl-2-oxo-2H-pyran-4-yloxy tosylzinc (II), by the oxidative addition of readily available zinc dust into the corresponding 4-tosylated coumarin (A) and pyrone (B), respectively. Of special interest, the thus-obtained zinc complexes showed an electrophile-dependent reactivity. The subsequent coupling reactions of I and II with a variety of acid chlorides provided the O-acylation product in moderate yields. More interestingly, it should be emphasized that the thus-prepared zinc complexes (I and II) functioned both as zinc enolate and zinc sulfinate, providing C(3)-disubstituted product (b) and sulfone (c), respectively, from a single-run reaction when I or II was treated with benzyl halides. Even though somewhat low yields were achieved under the nonoptimized conditions, the novel zinc complexes present another potential application for zinc reagents. Versatile applications of this discovery are currently underway

  19. Exploring the Saccharomyces cerevisiae Volatile Metabolome: Indigenous versus Commercial Strains

    Science.gov (United States)

    Alves, Zélia; Melo, André; Figueiredo, Ana Raquel; Coimbra, Manuel A.; Gomes, Ana C.; Rocha, Sílvia M.

    2015-01-01

    Winemaking is a highly industrialized process and a number of commercial Saccharomyces cerevisiae strains are used around the world, neglecting the diversity of native yeast strains that are responsible for the production of wines peculiar flavours. The aim of this study was to in-depth establish the S. cerevisiae volatile metabolome and to assess inter-strains variability. To fulfill this objective, two indigenous strains (BT2652 and BT2453 isolated from spontaneous fermentation of grapes collected in Bairrada Appellation, Portugal) and two commercial strains (CSc1 and CSc2) S. cerevisiae were analysed using a methodology based on advanced multidimensional gas chromatography (HS-SPME/GC×GC-ToFMS) tandem with multivariate analysis. A total of 257 volatile metabolites were identified, distributed over the chemical families of acetals, acids, alcohols, aldehydes, ketones, terpenic compounds, esters, ethers, furan-type compounds, hydrocarbons, pyrans, pyrazines and S-compounds. Some of these families are related with metabolic pathways of amino acid, carbohydrate and fatty acid metabolism as well as mono and sesquiterpenic biosynthesis. Principal Component Analysis (PCA) was used with a dataset comprising all variables (257 volatile components), and a distinction was observed between commercial and indigenous strains, which suggests inter-strains variability. In a second step, a subset containing esters and terpenic compounds (C10 and C15), metabolites of particular relevance to wine aroma, was also analysed using PCA. The terpenic and ester profiles express the strains variability and their potential contribution to the wine aromas, specially the BT2453, which produced the higher terpenic content. This research contributes to understand the metabolic diversity of indigenous wine microflora versus commercial strains and achieved knowledge that may be further exploited to produce wines with peculiar aroma properties. PMID:26600152

  20. Extraction and identification of bioactive components in Sida cordata (Burm.f.) using gas chromatography-mass spectrometry.

    Science.gov (United States)

    Ganesh, Mani; Mohankumar, Murugan

    2017-09-01

    Sida cordata (Burm.f.) is a pineal tropical plant in the family Malvaceae that is found throughout India and used to treat various diseases and ailments in many complementary and alternative medicine systems. This study identified the bioactive components present in whole-plant ethanol extracts of S . cordata using gas chromatography-mass spectrometry (GC-MS). Based on their retention times (RT) and mass-to-charge ratios (m/z), 29 bioactive compounds were identified: nonanoic acid, vitamin D 3 , 3-trifluroacetoxypentadecane, α-d-glucopyranoside, O-α-d-glucopyranosyl-(1.fwdarw.3)-α-d-fructofuranosyl,3,7,11,15-tetramethyl-2-hexadecan-1-ol, octadecanoic acid, ethyl ester, phytol, 9,12-octadecadienoic acid, methyl ester (E,E), 9,12,15-octadecadienoic acid, methyl ester (Z,Z,Z), oleic acid, 1,2-15,16-diepoxyhexadecane, 3-hexadecyloxycarbonyl-5-(2-hydroxyethyl)-4-methylimidazolium ion, methoxyacetic acid, 4-tetradecyl ester, 1,2-benzenedicarboxylic acid, mono (2-ethylhexyl) ester, 1-iodo-2-methylundecane, dodecane, 2,6,10-trimethyl-, 2-piperidinone-N-[4-bromo-n-butyl]-, squalene, octadecane-1-(ethenyloxy)-, Z,Z-2,5-pentadecadien-1-ol, 1-hexadecanol, 2-methyl-, spiro[androst-5ene-17,1'-cyclobutan]-2'-one-3-hydroxy-, (3a,17a)-, diethylene glycol monododecyl ether, vitamin E, cholestan-3-ol, 2-methylene-, (3a,5a)-, 2H-pyran, 2-(7-heptadecynyloxy)tetrahydro-, and cis -Z-α-bisabolene epoxide. The presence of various bioactive compounds justifies the use of this plant for treating various ailments by traditional practitioners.

  1. Structural insights, protein-ligand interactions and spectroscopic characterization of isoformononetin

    Science.gov (United States)

    Srivastava, Anubha; Singh, Harshita; Mishra, Rashmi; Dev, Kapil; Tandon, Poonam; Maurya, Rakesh

    2017-04-01

    Isoformononetin, a methoxylated isoflavone present in medicinal plants, has non-estrogenic bone forming effect via differential mitogen-activated protein kinase (MAPK) signaling. Spectroscopic (FT-Raman, FT-IR, UV-vis and NMR spectra) and quantum chemical calculations using density functional theory (DFT) and 6-311++G(d,p) as a large basis set have been employed to study the structural and electronic properties of isoformononetin. A detailed conformational analysis is performed to determine the stability among conformers and the various possibilities of intramolecular hydrogen bonding formation. Molecular docking studies with different protein kinases were performed on isoformononetin and previously studied isoflavonoid, formononetin in order to understand their inhibitory nature and the effect of functional groups on osteogenic or osteoporosis associated proteins. It is found that the oxygen atoms of methoxy, hydroxyl groups attached to phenyl rings R1, R3 and carbonyl group attached to pyran ring R2, play a major role in binding with the protein kinases that is responsible for the osteoporosis; however, no hydrophobic interactions are observed between rings of ligand and protein. The electronic properties such as HOMO and LUMO energies were determined by time-dependent TD-DFT which predict that conformer II is a little bit more stable and chemically low reactive than conformer I of isoformononetin. To estimate the structure-activity relationship, the molecular electrostatic potential (MEP) surface map, and reactivity descriptors are calculated from the optimized geometry of the molecule. From these results, it is also found that isoformononetin is kinetically more stable, less toxic, weak electrophile and chemically less reactive than formononetin. The atoms in molecules and natural bond orbital analysis are applied for the detailed analysis of intra and intermolecular hydrogen bonding interactions.

  2. Synthesis of 5α-Androstane-17-spiro-δ-lactones with a 3-Keto, 3-Hydroxy, 3-Spirocarbamate or 3-Spiromorpholinone as Inhibitors of 17β-Hydroxysteroid Dehydrogenases

    Directory of Open Access Journals (Sweden)

    Donald Poirier

    2013-01-01

    Full Text Available We synthesized two series of androstane derivatives as inhibitors of type 3 and type 5 17β-hydroxysteroid dehydrogenases (17β-HSDs. In the first series, four monospiro derivatives at position C17 were prepared from androsterone (ADT or epi-ADT. After the protection of the alcohol at C3, the C17-ketone was alkylated with the lithium acetylide of tetrahydro-2-(but-3-ynyl-2-H-pyran, the triple bond was hydrogenated, the protecting groups hydrolysed and the alcohols oxidized to give the corresponding 3-keto-17-spiro-lactone derivative. The other three compounds were generated from this keto-lactone by reducing the ketone at C3, or by introducing one or two methyl groups. In the second series, two dispiro derivatives at C3 and C17 were prepared from epi-ADT. After introducing a spiro-δ-lactone at C17 and an oxirane at C3, an aminolysis of the oxirane with L-isoleucine methyl ester provided an amino alcohol, which was treated with triphosgene or sodium methylate to afford a carbamate- or a morpholinone-androstane derivative, respectively. These steroid derivatives inhibited 17β-HSD3 (14–88% at 1 μM; 46–94% at 10 μM and 17β-HSD5 (54–73% at 0.3 μM; 91–92% at 3 μM. They did not produce any androgenic activity and did not bind steroid (androgen, estrogen, glucocorticoid and progestin receptors, suggesting a good profile for prostate cancer therapy.

  3. QSAR analysis on Spodoptera litura antifeedant activities for flavone derivatives

    International Nuclear Information System (INIS)

    Duchowicz, Pablo R.; Goodarzi, Mohammad; Ocsachoque, Marco A.; Romanelli, Gustavo P.; Ortiz, Erlinda del V.; Autino, Juan C.; Bennardi, Daniel O.; Ruiz, Diego M.; Castro, Eduardo A.

    2009-01-01

    We establish useful models that relate experimentally measured biological activities of compounds to their molecular structure. The pED 50 feeding inhibition on Spodoptera litura species exhibited by aurones, chromones, 3-coumarones and flavones is analyzed in this work through the hypothesis encompassed in the Quantitative Structure-Activity Relationships (QSAR) Theory. This constitutes a first necessary computationally based step during the design of more bio-friendly repellents that could lead to insights for improving the insecticidal activities of the investigated compounds. After optimizing the molecular structure of each furane and pyrane benzoderivative with the semiempirical molecular orbitals method PM3, more than a thousand of constitutional, topological, geometrical and electronic descriptors are calculated and multiparametric linear regression models are established on the antifeedant potencies. The feature selection method employed in this study is the Replacement Method, which has proven to be successful in previous analyzes. We establish the QSAR both for the complete molecular set of compounds and also for each chemical class, so that acceptably describing the variation of the inhibitory activities from the knowledge of their structure and thus achieving useful predictive results. The main interest of developing trustful QSAR models is that these enable the prediction of compounds having no experimentally measured activities for any reason. Therefore, the structure-activity relationships are further employed for investigating the antifeedant activity on previously synthesized 2-,7-substituted benzopyranes, which do not pose any measured values on the biological expression. One of them, 2-(α-naphtyl)-4H-1-benzopyran-4-one, results in a promising structure to be experimentally analyzed as it has predicted pED 50 = 1.162.

  4. A simple QuEChERS-like extraction approach for molecular chemical characterization of organic aerosols: application to nitrated and oxygenated PAH derivatives (NPAH and OPAH) quantified by GC-NICIMS.

    Science.gov (United States)

    Albinet, A; Nalin, F; Tomaz, S; Beaumont, J; Lestremau, F

    2014-05-01

    An extraction procedure based on the Quick Easy Cheap Effective Rugged and Safe (QuEChERS) approach has been developed and used for analysis of particle-bound nitrated and oxygenated PAH derivatives (NPAH and OPAH, respectively). Several analytical conditions, for example GC injection temperature and MS detection settings, were optimized. This analytical procedure enabled simultaneous GC-NICIMS quantification of 32 NPAH and 32 OPAH (or other oxygenated compounds), including typical components of secondary organic aerosol (SOA) formed by photooxidation of PAH (e.g. 2-formyl-trans-cinnamaldehyde and 6H-dibenzo[b,d]pyran-6-one). The QuEChERS-like approach was optimized, including the nature of the extraction solvent, the sorbent used for clean-up, and extraction time. The final extraction procedure was based on brief mechanical agitation (vortex mixing for 1.5 min), with 7 mL acetonitrile as solvent. Because dispersive solid-phase extraction (d-SPE) did not provide satisfactory results, SPE using SiO2 was selected for sample purification. Identical results were obtained when the QuEChERS-like and traditional pressurised solvent extraction (PLE) procedures were compared for analysis of fortified ambient air particle samples. The procedure was validated by analysis of two aerosol standard reference materials (NIST SRM 1649b (urban dust) and SRM 2787 (fine particulate matter, extraction methods, including PLE, the QuEChERS-like procedure resulted in increased productivity and reduced extraction cost. This paper shows that QuEChERS-like extraction procedures can be suitably adapted for molecular chemical characterization of aerosol samples and could be extended to other categories of compound.

  5. Phyto chemical Protection against Diethylnitrosoamine Induced Hepato carcinogenesis by Trigonella foenum graecum in Female Rats

    Energy Technology Data Exchange (ETDEWEB)

    Abdelgawad, M R; Mustafa, M M.M.; Kottb, M K.I. [Egyptian Atomic Energy Authority, Nuclear Research Center, Biological Applications Department, Cairo (Egypt)

    2012-05-15

    Trigonella foenum graecum (fenugreek) is traditionally used to treat. Recent studies suggest that fenugreek and its active constituents may possess anti carcinogenic potential. The preventive efficacy of dietary fenugreek seed 2% and 4% (w/w feed) on diethylnitrosamine-induced rat liver carcinogenesis were evaluated. Rats were sacrificed when rats became very weak with unstable shelf live were chosen as an end point. Egypt is an Islamic country alcoholic prohibition so the possible use of ethanol extraction may be accepted with high restriction towards its applications in human, that it may affect the active constituents of fenugreek seeds. Whereby, fenugreek seeds contain >8% oil, many valuable phenolic compounds, protein and amino acids, etc ... with different concentrations according to the extraction method. So, the present study was carried out to evaluate the effect of fenugreek powder on adult female rats fed experimental diets containing 2% or 4% (w/w) fenugreek seed powder (FSP) for 2 weeks and have phenobarbital in a dose of 200 mg/L ad lib. before and after a single injection with diethylnitrosamine (200 mg/kg body weight). Rats were sacrificed 20 weeks after intra-peritoneal (i.p) diethylnitrosamine injection and their livers, spleens, kidneys and lungs were excised washed well with cold saline, weighted and processed through paraffin wax preparation, staining and pathological changes were examined. It was found that, by comparison with control, continuous feeding of FSP 2% and 4% suppressed hepatocarcinogensity up to 20% and 50%, respectively. In addition, on the basis of these findings, the invaluable and precious fenugreek constituents are diosgenin [(25 R)-5-spirosten-3h-ol] and [5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3,4,5-trihydroxy-6(hydroxymethyl) tetra- hydro-2H-pyran-2-yl)chroman-4-one] besides, others. Finally, fenugreek seeds seem to have potential role as a novel cancer preventive agent and that needs further investigations

  6. Tetrathiapentalene-based organic conductors

    Energy Technology Data Exchange (ETDEWEB)

    Misaki, Yohji, E-mail: misaki@eng.ehime-u.ac.j [Department of Applied Chemistry, Graduate School of Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama 790-8577 (Japan)

    2009-04-15

    The synthesis, structure and properties of tetrathiapentalene-based (TTP) organic conductors are reviewed. Among various TTP-type donors, bis-fused tetrathiafulvalene, 2,5-bis(1,3-dithiol-2-ylidene)-1,3,4,6-tetrathiapentalene (BDT-TTP) and its derivatives afford many metallic radical cation salts stable down to low temperatures, regardless of the size and shape of the counter anions. Most BDT-TTP conductors have a {beta}-type donor arrangement with almost uniform stacks. Introduction of appropriate substituents results in molecular packing that differs from the {beta}-type. A vinylogous TTP, 2-(1,3-dithiol-2-ylidene)-5-(2-ethanediylidene-1,3-dithiole) -1,3,4,6-tetrathiapentalene (DTEDT) has yielded an organic superconductor (DTEDT){sub 3}Au(CN){sub 2} as well as metallic radical cation salts, regardless of the counter anions. (Thio)pyran analogs of TTP, namely (T)PDT-TTP and its derivatives produce molecular conductors with novel molecular arrangements. A TTP analog with reduced {pi}-electron system 2,5-bis(1,3-dithian-2-ylidene)-1,3,4,6-tetrathiapentalene (BDA-TTP) has afforded several organic superconductors. Highly conducting molecular metals with unusual oxidation states (+1, +5/3 and neutral) have been developed on the basis of 2,5-bis(1,3-dithiol-2-ylidene)-1,3,4,6-tetrathiapentalene (BDT-TTP) derivatives and analogous metal derivatives M(dt){sub 2} (M = Ni, Au). (topical review)

  7. Deoxyarbutin Possesses a Potent Skin-Lightening Capacity with No Discernible Cytotoxicity against Melanosomes.

    Directory of Open Access Journals (Sweden)

    Fang Miao

    Full Text Available Safe and effective ingredients capable of removing undesired hyperpigmentation from facial skin are urgently needed for both pharmaceutical and cosmetic purposes. Deoxyarbutin (4-[(tetrahydro-2H-pyran-2-yl oxy] phenol, D-Arb is a glucoside derivative of hydroquinone. Here, we investigated the toxicity and efficacy of D-Arb at the sub-cellular level (directly on melanosomes and skin pigmentation using in vivo and in vitro models to compare with its parent compound hydroquinone (1,4-benzenediol, HQ. At first, we examined the ultrastructural changes of melanosomes in hyperpigmented guinea pig skin induced by 308-nm monochromatic excimer lightand/or treated with HQ and D-Arb using transmission electron microscopy. The results showed that prominent changes in the melanosomal membrane, such as bulb-like structure and even complete rupture of the outer membranes, were found in the skin after topical application of 5% HQ for 10 days. These changes were barely observed in the skin treated with D-Arb. To further clarify whether membrane toxicity of HQ was a direct result of the compound treatment, we also examinedultrastructural changes of individual melanosomes purified from MNT1 human melanoma cells. Similar observations were obtained from the naked melanosome model in vitro. Finally, we determined the effects of melanosomal fractions exposed to HQ or D-Arb on hydroxyl radical generation in the Fenton reaction utilizing an electron spin resonance assay. D-Arb-treated melanosomesexhibit a moderate hydroxyl radical-scavenging activity, whereas HQ-treated melanosomessignificantly generate more hydroxyl free radicals. This study suggests that D-Arb possesses a potent ability in skin lightening and antioxidation with less melanosome cytotoxicity.

  8. Deoxyarbutin Possesses a Potent Skin-Lightening Capacity with No Discernible Cytotoxicity against Melanosomes.

    Science.gov (United States)

    Miao, Fang; Shi, Ying; Fan, Zhi-Feng; Jiang, Shan; Xu, Shi-Zheng; Lei, Tie-Chi

    2016-01-01

    Safe and effective ingredients capable of removing undesired hyperpigmentation from facial skin are urgently needed for both pharmaceutical and cosmetic purposes. Deoxyarbutin (4-[(tetrahydro-2H-pyran-2-yl) oxy] phenol, D-Arb) is a glucoside derivative of hydroquinone. Here, we investigated the toxicity and efficacy of D-Arb at the sub-cellular level (directly on melanosomes) and skin pigmentation using in vivo and in vitro models to compare with its parent compound hydroquinone (1,4-benzenediol, HQ). At first, we examined the ultrastructural changes of melanosomes in hyperpigmented guinea pig skin induced by 308-nm monochromatic excimer lightand/or treated with HQ and D-Arb using transmission electron microscopy. The results showed that prominent changes in the melanosomal membrane, such as bulb-like structure and even complete rupture of the outer membranes, were found in the skin after topical application of 5% HQ for 10 days. These changes were barely observed in the skin treated with D-Arb. To further clarify whether membrane toxicity of HQ was a direct result of the compound treatment, we also examinedultrastructural changes of individual melanosomes purified from MNT1 human melanoma cells. Similar observations were obtained from the naked melanosome model in vitro. Finally, we determined the effects of melanosomal fractions exposed to HQ or D-Arb on hydroxyl radical generation in the Fenton reaction utilizing an electron spin resonance assay. D-Arb-treated melanosomesexhibit a moderate hydroxyl radical-scavenging activity, whereas HQ-treated melanosomessignificantly generate more hydroxyl free radicals. This study suggests that D-Arb possesses a potent ability in skin lightening and antioxidation with less melanosome cytotoxicity.

  9. Efficient protocol for isolation and purification of different soyasaponins from soy hypocotyls.

    Science.gov (United States)

    Zhao, Dayun; Yan, Mingxia; Huang, Yuai; Sun, Xiangjun

    2012-12-01

    Soyasaponins are naturally occurring triterpenoid glycosides associated with many biological activities. The aim of the present study was to develop an effective method for isolation and purification of differently glycosylated, acetylated, and 2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP)-conjugated soyasaponins from soy hypocotyls. Both gel filtration using Sephadex LH-20 chromatography (Amersham Pharmacia Biotech AB; elution phase: methanol, flow rate: 3.0 mL/min, sample loading: 60 mg) and high-speed countercurrent chromatography (stationary phase: n-butanol-acetic acid (5.0%, v/v), mobile phase: water flow rate: 3.0 mL/min, sample loading: 100 mg) could effectively fractionate isoflavones and soyasaponins from the crude extract with yield of soyasaponin complexes 20.5 mg and 22.3 mg, respectively. After fractionation, the soyasaponin complexes could be purified further using preparative HPLC to separate individuals. A total of nine soyasaponins, triacetyl soyasaponin Ab (yield 1.55%, HPLC purity >98%), Aa (2.68%, >99%), Ab (18.53%, >98%), Ae (0.85%, >98%), Ba (0.63%, >91%), Af (1.12%, >85%), Bb (3.45%, >98%) and Be (0.59%, >76.8%) were obtained. DDMP-conjugated groups, αg (2.06%, >85%), βg (7.59%, >85%), and γg (0.29%, >85%) that were very labile even in mild conditions, were also collected. The method described here can be used as an effective protocol to separate different soyasaponins occurring in the original sample. © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  10. Genotoxicity of waterpipe smoke in buccal cells and peripheral blood leukocytes as determined by comet assay.

    Science.gov (United States)

    Al-Amrah, Hadba Jar-Allah; Aboznada, Osama Abdullah; Alam, Mohammad Zubair; ElAssouli, M-Zaki Mustafa; Mujallid, Mohammad Ibrahim; ElAssouli, Sufian Mohamad

    2014-12-01

    Waterpipe smoke causes DNA damage in peripheral blood leukocytes and in buccal cells of smokers. To determine the exposure effect of waterpipe smoke on buccal cells and peripheral blood leukocytes in regard to DNA damage using comet assay. The waterpipe smoke condensates were analyzed by gas chromatography-mass spectrometry (GC-MS). The study was performed on 20 waterpipe smokers. To perform comet assay on bucaal cells of smokers, 10 µl of cell suspension was mixed with 85 µl of pre-warmed 1% low melting agarose, applied to comet slide and electrophoresed. To analyze the effect of smoke condensate in vitro, 1 ml of peripheral blood was mixed with 10 µl of smoke condensate and subjected for comet assay. The GC-MS analysis revealed the presence of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4on, nicotine, hydroxymethyl furancarboxaldehyde and 3-ethoxy-4-hydroxybenzaldehyde in the smoke condensates. Waterpipe smoking caused DNA damage in vivo in buccal cells of smokers. The tail moment and tail length in buccal cells of smokers were 186 ± 26 and 456 ± 71, respectively, which are higher than control. The jurak and moassel smoke condensates were found to cause DNA damage in peripheral blood leukocytes. The moassel smoke condensate was more damaging. There is wide misconception that waterpipe smoking is not as harmful as cigarette smoking. This study demonstrated that waterpipe smoke induced DNA damage in exposed cells. Waterpipe smokes cause DNA damage in buccal cells. The smoke condensate of both jurak and moassel caused comet formation suggesting DNA damage in peripheral blood leukocytes.

  11. Transparent organic light-emitting diodes with different bi-directional emission colors using color-conversion capping layers

    Energy Technology Data Exchange (ETDEWEB)

    Lee, Jonghee, E-mail: jonghee.lee@etri.re.kr [OLED Research Center, Electronics and Telecommunications Research Institute (ETRI), Daejeon 305-700 (Korea, Republic of); Institut für Angewandte Photophysik, Technische Universität Dresden, George-Bähr-Straße 1, 01062 Dresden (Germany); Koh, Tae-Wook [Department of Electrical Engineering, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 305-701 (Korea, Republic of); Cho, Hyunsu [OLED Research Center, Electronics and Telecommunications Research Institute (ETRI), Daejeon 305-700 (Korea, Republic of); Department of Electrical Engineering, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 305-701 (Korea, Republic of); Schwab, Tobias [Institut für Angewandte Photophysik, Technische Universität Dresden, George-Bähr-Straße 1, 01062 Dresden (Germany); Lee, Jae-Hyun [Department School of Global Convergence Studies, Hanbat National University, San 16-1, Duckmyoung-dong, Daejeon 305-719 (Korea, Republic of); Hofmann, Simone [Institut für Angewandte Photophysik, Technische Universität Dresden, George-Bähr-Straße 1, 01062 Dresden (Germany); Lee, Jeong-Ik [OLED Research Center, Electronics and Telecommunications Research Institute (ETRI), Daejeon 305-700 (Korea, Republic of); Yoo, Seunghyup [Department of Electrical Engineering, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 305-701 (Korea, Republic of); and others

    2015-06-15

    We report a study on transparent organic light-emitting diodes (OLEDs) with different bi-directional emission colors, enabled by color-conversion organic capping layers. Starting from a transparent blue OLED with an uncapped Ag top electrode exhibiting an average transmittance of 33.9%, a 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran (DCM)-doped tris-(8-hydroxy-quinolinato)-aluminum (Alq3) capping layer is applied to achieve color-conversion from blue to orange-red on the top side while maintaining almost unchanged device transmittance. This color-conversion capping layer does not only change the color of the top side emission, but also enhances the overall device efficiency due to the optical interaction of the capping layer with the primary blue transparent OLED. Top white emission from the transparent bi-directional OLED exhibits a correlated color temperature around 6000–7000 K, with excellent color stability as evidenced by an extremely small variation in color coordinate of Δ(x,y)=(0.002, 0.002) in the forward luminance range of 100–1000 cd m{sup −2}. At the same time, the blue emission color of bottom side is not influenced by the color conversion capping layer, which finally results in different emission colors of the two opposite sides of our transparent OLEDs. - Highlights: • We report transparent organic light-emitting diodes (OLEDs) with different bi-directional emission colors. • Transparent blue OLED with color-conversion organic capping layers (CCL) shows orange top side emission. • Top white emission exhibits a CCT around 7000 K, with excellent color stability on a driving voltage.

  12. Solid state solvation effect and reduced amplified spontaneous emission threshold value of glass forming DCM derivative in PMMA films

    Energy Technology Data Exchange (ETDEWEB)

    Vembris, Aivars, E-mail: aivars.vembris@cfi.lu.lv [Institute of Solid State Physics, University of Latvia, 8 Kengaraga Street, Riga LV 1063 (Latvia); Zarins, Elmars; Kokars, Valdis [Institute of Applied Chemistry, Riga Technical University, 14/24 Azenes Street, Riga LV 1048 (Latvia)

    2015-02-15

    Molecule crystallization is one of the limitations for obtaining high-gain organic laser systems. One of the examples is well known red laser dye 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran (DCM). The lowest threshold value of amplified spontaneous emission was achieved by doping 2 wt% of DCM molecule in tris-(8-hydroxy quinoline) aluminum (Alq{sub 3}) matrix. Further increase of the DCM dye concentration makes the system less efficient as its threshold value increases. It is due to large intermolecular interaction, which induces photoluminescence quenching. Compounds with reduced intermolecular interaction could be prospective in organic laser systems due to higher possible doping. In this work photoluminescence and amplified spontaneous emission properties of modified DCM molecule in poly(methyl methacrylate) (PMMA) matrix were investigated. Bulky trityloxyethyl groups were attached to the donor part of DCM. These groups increase intermolecular distance wherewith reduce photoluminescence quenching. More than one order of magnitude lower excitation threshold energy of the amplified spontaneous emission was achieved in doped polymer films with investigated compound in comparison to doped polymer with DCM. It means that the investigated compound is more perspective as a laser material compared to the previously studied. In addition, amplified spontaneous emission maximum could be tuned within 15 nm by changing concentration from 0.1 wt% to 10 wt% DWK-1 in PMMA matrix due to solid state solvation effect. - Highlights: • Bulky groups attached to DCM dye reduce photoluminescence quenching. • Amplified spontaneous emission is in red spectral region. • Amplified spontaneous emission spectra were tuned by 15 nm. • Amplified spontaneous emission threshold value was reduced by one order of magnitude.

  13. Combined optical gain and degradation measurements in DCM2 doped Tris-(8-hydroxyquinoline)aluminum thin-films

    Science.gov (United States)

    Čehovski, Marko; Döring, Sebastian; Rabe, Torsten; Caspary, Reinhard; Kowalsky, Wolfgang

    2016-04-01

    Organic laser sources offer the opportunity to integrate flexible and widely tunable lasers in polymer waveguide circuits, e.g. for Lab-on-Foil applications. Therefore, it is necessary to understand gain and degradation processes for long-term operation. In this paper we address the challenge of life-time (degradation) measurements of photoluminescence (PL) and optical gain in thin-film lasers. The well known guest-host system of aluminum-chelate Alq3 (Tris-(8-hydroxyquinoline)aluminum) as host material and the laser dye DCM2 (4-(Dicyanomethylene)-2- methyl-6-julolidyl-9-enyl-4H-pyran) as guest material is employed as laser active material. Sample layers have been built up by co-evaporation in an ultrahigh (UHV) vacuum chamber. 200nm thick films of Alq3:DCM2 with different doping concentrations have been processed onto glass and thermally oxidized silicon substrates. The gain measurements have been performed by the variable stripe length (VSL) method. This measurement technique allows to determine the thin-film waveguide gain and loss, respectively. For the measurements the samples were excited with UV irradiation (ƛ = 355nm) under nitrogen atmosphere by a passively Q-switched laser source. PL degradation measurements with regard to the optical gain have been done at laser threshold (approximately 3 μJ/cm2), five times above laser threshold and 10 times above laser threshold. A t50-PL lifetime of > 107 pulses could be measured at a maximum excitation energy density of 32 μJ/cm2. This allows for a detailed analysis of the gain degradation mechanism and therefore of the stimulated cross section. Depending on the DCM2 doping concentration C the stimulated cross section was reduced by 35 %. Nevertheless, the results emphasizes the necessity of the investigation of degradation processes in organic laser sources for long-term applications.

  14. Maillard reaction of lactose and fluoxetine hydrochloride, a secondary amine.

    Science.gov (United States)

    Wirth, D D; Baertschi, S W; Johnson, R A; Maple, S R; Miller, M S; Hallenbeck, D K; Gregg, S M

    1998-01-01

    Analysis of commercially available generic formulations of fluoxetine HCl revealed the presence of lactose as the most common excipient. We show that such formulations are inherently less stable than formulations with starch as the diluent due to the Maillard reaction between the drug, a secondary amine hydrochloride, and lactose. The Amadori rearrangement product was isolated and characterized; the characterization was aided by reduction with sodium borohydride and subsequent characterization of this reduced adduct. The lactose-fluoxetine HCl reaction was examined in aqueous ethanol and in the solid state, in which factors such as water content, lubricant concentration, and temperature were found to influence the degradation. N-Formylfluoxetine was identified as a major product of this Maillard reaction and it is proposed that N-formyl compounds be used as markers for this drug-excipient interaction since they are easy to prepare synthetically. Many characteristic volatile products of the Maillard reaction have been identified by GC/MS, including furaldehyde, maltol, and 2,3-dihydro-3,5-dihydroxy-6-methyl-4 H-pyran-4-one. Close similarity between the degradation products of simple mixtures and formulated generic products was found; however, at least one product decomposed at a rate nearly 10 times that predicted from the simple models. Maillard products have also been identified in unstressed capsules. The main conclusion is that drugs which are secondary amines (not just primary amines as sometimes reported) undergo the Maillard reaction with lactose under pharmaceutically relevant conditions. This finding should be considered during the selection of excipients and stability protocols for drugs which are secondary amines or their salts, just as it currently is for primary amines.

  15. A sensitive fluorescent probe for the polar solvation dynamics at protein-surfactant interfaces.

    Science.gov (United States)

    Singh, Priya; Choudhury, Susobhan; Singha, Subhankar; Jun, Yongwoong; Chakraborty, Sandipan; Sengupta, Jhimli; Das, Ranjan; Ahn, Kyo-Han; Pal, Samir Kumar

    2017-05-17

    Relaxation dynamics at the surface of biologically important macromolecules is important taking into account their functionality in molecular recognition. Over the years it has been shown that the solvation dynamics of a fluorescent probe at biomolecular surfaces and interfaces account for the relaxation dynamics of polar residues and associated water molecules. However, the sensitivity of the dynamics depends largely on the localization and exposure of the probe. For noncovalent fluorescent probes, localization at the region of interest in addition to surface exposure is an added challenge compared to the covalently attached probes at the biological interfaces. Here we have used a synthesized donor-acceptor type dipolar fluorophore, 6-acetyl-(2-((4-hydroxycyclohexyl)(methyl)amino)naphthalene) (ACYMAN), for the investigation of the solvation dynamics of a model protein-surfactant interface. A significant structural rearrangement of a model histone protein (H1) upon interaction with anionic surfactant sodium dodecyl sulphate (SDS) as revealed from the circular dichroism (CD) studies is nicely corroborated in the solvation dynamics of the probe at the interface. The polarization gated fluorescence anisotropy of the probe compared to that at the SDS micellar surface clearly reveals the localization of the probe at the protein-surfactant interface. We have also compared the sensitivity of ACYMAN with other solvation probes including coumarin 500 (C500) and 4-(dicyanomethylene)-2-methyl-6-(p-dimethylamino-styryl)-4H-pyran (DCM). In comparison to ACYMAN, both C500 and DCM fail to probe the interfacial solvation dynamics of a model protein-surfactant interface. While C500 is found to be delocalized from the protein-surfactant interface, DCM becomes destabilized upon the formation of the interface (protein-surfactant complex). The timescales obtained from this novel probe have also been compared with other femtosecond resolved studies and molecular dynamics simulations.

  16. Synthesis, antitumour and antioxidant activities of novel α,β-unsaturated ketones and related heterocyclic analogues: EGFR inhibition and molecular modelling study.

    Science.gov (United States)

    El-Husseiny, Walaa M; El-Sayed, Magda A-A; Abdel-Aziz, Naglaa I; El-Azab, Adel S; Ahmed, Esam R; Abdel-Aziz, Alaa A-M

    2018-12-01

    New α,β-unsaturated ketones 4a,b; 5a-c; and 6a,b; as well as 4-H pyran 7; pyrazoline 8a,b; isoxazoline 9; pyridine 10-11; and quinoline-4-carboxylic acid 12a,b derivatives were synthesized and evaluated for in vitro antitumour activity against HepG2, MCF-7, HeLa, and PC-3 cancer cell lines. Antioxidant activity was investigated by the ability of these compounds to scavenge the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation (ABTS •+ ). Compounds 6a, 6b, 7, and 8b exhibited potent antitumour activities against all tested cell lines with [IC 50 ] ≅5.5-18.1 µΜ), in addition to significantly high ABTS •+ scavenging activities. In vitro EGFR kinase assay for 6a, 6b, 7, and 8b as the most potent antitumour compounds showed that; compounds 6b, and 7 exhibited worthy EGFR inhibition activity with IC 50 values of 0.56 and 1.6 µM, respectively, while compounds 6a and 8b showed good inhibition activity with IC 50 values of 4.66 and 2.16 µM, respectively, compared with sorafenib reference drug (IC 50  = 1.28 µM). Molecular modelling studies for compounds 6b, 7, and 8b were conducted to exhibit the binding mode towards EGFR kinase, which showed similar interaction with erlotinib.

  17. Red organic light-emitting diodes based on wide band gap emitting material as the host utilizing two-step energy transfer

    International Nuclear Information System (INIS)

    Haq Khizarul; Shanpeng Liu; Khan, M A; Jiang, X Y; Zhang, Z L; Zhu, W Q

    2008-01-01

    We demonstrated efficient red organic light-emitting diodes based on a host emitting system of 9,10-di(2-naphthyl)anthracene (ADN) co-doped with 4-(dicyano-methylene)-2-t-butyle-6- (1,1,7,7-tetramethyl-julolidyl-9-enyl)-4H-pyran (DCJTB) as a red dopant and 2,3,6,7- tetrahydro-1,1,7,7-tetramethyl-1H,5H,1 1H-10(2-benzothiazolyl)-quinolizine-[9,9a,1gh] coumarin (C545T) as an assistant dopant. The typical device structure was glass substrate/ITO/4,4',4''-tris(N-3-methylphenyl-N-phenylamino) triphenylamine(m-MTDATA)/N,N'-bis-(naphthalene-1-yl)-N,N'-diphenylbenzidine (NPB)/[ADN: DCJTB: C545T/Alq 3 /LiF/Al]. It was found that C545T dopant did not emit by itself but did assist the energy transfer from the host (ADN) to the red emitting dopant. The red OLEDs realized by this approach not only enhanced the emission color, but also significantly improved the EL efficiency. The EL efficiency reached 3.5 cd A −1 at a current density of 20 mA cm −2 , which is enhanced by three times compared with devices where the emissive layer is composed of the DCJTB doped ADN. The saturated red emission was obtained with CIE coordinates (x = 0.618, y = 0.373) at 621 nm, and the device driving voltage is decreased as much as 38%. We attribute these improvements to the assistant dopant (C545T), which leads to the more efficient energy transfer from ADN to DCJTB. These results indicate that the co-doped system is a promising method for obtaining high-efficiency red OLEDs

  18. Characterization of Chemical Compounds with Antioxidant and Cytotoxic Activities in Bougainvillea x buttiana Holttum and Standl, (var. Rose Extracts

    Directory of Open Access Journals (Sweden)

    Rodolfo Abarca-Vargas

    2016-12-01

    Full Text Available Bougainvillea is widely used in traditional Mexican medicine to treat several diseases. This study was designed to characterize the chemical constituents of B. x buttiana extracts with antioxidant and cytotoxic activities using different solvents. The extraction solvents used were as follows: distilled water (dH2O, methanol (MeOH, acetone (DMK, ethanol (EtOH, ethyl acetate (EtOAc, dichloromethane (DCM, and hexane (Hex (100% at an extraction temperature of 26 °C. Analysis of bioactive compounds present in the B. x buttiana extracts included the application of common phytochemical screening assays, GC-MS analysis, and cytotoxicity and antioxidant assays. The results show that the highest extraction yield was observed with water and methanol. The maximum total phenolic content amount and highest antioxidant potential were obtained when extraction with methanol was used. With the exceptions of water and ethanol extractions, all other extracts showed cytotoxicity ranging between 31% and 50%. The prevailing compounds in water, methanol, ethanol, and acetone solvents were as follows: 4H-pyran-4-one, 2,3-dihydro-3, 5-dihydroxy-6-methyl (2, 2-propenoic acid, 3-(2-hydrophenyl-(E- (3, and 3-O-methyl-d-glucose (6. By contrast, the major components in the experiments using solvents such as EtOH, DMK, EtOAc, DCM, and Hex were n-hexadecanoic acid (8, 9,12-octadecadienoic acid (Z,Z (12; 9-octadecenoic acid (E- (13, and stigmasta-5,22-dien-3-ol (28.

  19. Mononuclear late first row transition metal complexes of ONO donor hydrazone ligand: Synthesis, characterization, crystallographic insight, in vivo and in vitro anti-inflammatory activity

    Science.gov (United States)

    Kendur, Umashri; Chimmalagi, Geeta H.; Patil, Sunil M.; Gudasi, Kalagouda B.; Frampton, Christopher S.; Mangannavar, Chandrashekhar V.; Muchchandi, Iranna S.

    2018-02-01

    Air and moisture stable coordination compounds of late first row transition metal ions, viz., Co(II), Ni(II), Cu(II) and Zn(II) with a newly designed ligand, (E)-2-amino-N'-(1-(2-hydroxy-6-methyl-4-oxo-4H-pyran-3-yl)ethylidene)benzohydrazide (H2L) were prepared and extensively characterized using various spectro-analytical techniques. The ligand acts both in mono as well as doubly deprotonated manner. The ligand to metal stoichiometry was found to be 1:2 in case of complexes using chloride salts, whereas 1:1 in case of copper (II) complex using its acetate salt. The molecular structures of H2L, nickel and copper complexes were unambiguously determined by single-crystal X-ray diffraction studies reveal that H2L exists in a zwitterionic form while copper complex has copper centre in a distorted square planar environment. On the other hand, cobalt, nickel and zinc complexes display distorted octahedral coordination around the metal ion. In case of [Ni(HL)2].H2O, intramolecular Csbnd H⋯π stacking interaction were observed between the centroid of five membered chelate ring and phenyl proton C5sbnd H5 and intermolecular Csbnd H⋯π stacking interaction between the centroid of phenyl ring, dehydroacetic acid (DHA) ring and phenyl protons. The [Cu(L)DMF] complex is stabilized by intramolecular hydrogen bonding N1H⋯N2 and by intermolecular hydrogen bonding N1H⋯O4. Intermolecular interactions were investigated by Hirshfeld surfaces. Further, H2L and its metal complexes were screened for their in vivo and in vitro anti-inflammatory activities. The activity of the ligand has enhanced on coordination with transition metals. The tested compounds have shown excellent activity, which is almost equipotent to the standard used in the study.

  20. Carrier transport assisted by dopants in doped poly(N-vinylcarbozole) light-emitting diodes

    Energy Technology Data Exchange (ETDEWEB)

    Chen Xiaohong [Institute of Optoelectronic Technology, Bejing Jiaotong University, Beijing 100044 (China); Liu Ming [Institute of Optoelectronic Technology, Bejing Jiaotong University, Beijing 100044 (China); Xu Zheng [Institute of Optoelectronic Technology, Bejing Jiaotong University, Beijing 100044 (China); Hou Yanbing [Institute of Optoelectronic Technology, Bejing Jiaotong University, Beijing 100044 (China); Teng Feng [Institute of Optoelectronic Technology, Bejing Jiaotong University, Beijing 100044 (China); Xu Xurong [Institute of Optoelectronic Technology, Bejing Jiaotong University, Beijing 100044 (China)

    2004-04-07

    We have investigated the transient electroluminescence (EL) onset of the double-layer light-emitting devices made from poly(N-vinylcarbozole) (PVK) doped with 4-(dicyanomethylene)-2-t-butyl-6(1, 1, 7, 7-tetramethyljulolidyl-9-enyl)-4H-pyran (DCJTB) and tris(8-hydroxy-quinoline) aluminium (Alq{sub 3}). For the double-layered device in which PVK was doped with 0.1 wt% DCJTB, the EL onset of PVK lags that of DCJTB and Alq{sub 3}, while the EL onset of DCJTB and Alq{sub 3} is simultaneous. However, the EL emission of the double-layered device of PVK/Alq{sub 3} originates only from Alq{sub 3}. The results show that DCJTB dopants can not only help to tunnel electrons from Alq{sub 3} zone to PVK but can also assist electrons transfer in PVK under high electric field by hopping between DCJTB molecules or from DCJTB to PVK sites at a low doping concentration of 0.1 wt%. When the DCJTB doping concentration is 4.0 wt%, the EL onset of Alq{sub 3} lags that of DCJTB. The difference in the EL onsets of DCJTB, Alq{sub 3} and PVK is attributed to the slow build-up of the internal space charge in the vicinity of the interface between PVK and Alq{sub 3}. The electron potential difference of the interface between Alq{sub 3} and PVK doped by DCJTB can be adjusted by changing the DCJTB doping concentration in double-layer devices.

  1. Luminescence of Rubrene and DCJTB molecules in organic light-emitting devices

    Energy Technology Data Exchange (ETDEWEB)

    Moon, Chang-Bum, E-mail: cbmoon@hoseo.edu [Department of Display Engineering, Hoseo University, Sechul-Ri 160, Baebang, Asan, Chung-Nam 336-795 (Korea, Republic of); Department of Engineering Physics, McMaster University, Hamilton, Ontario, Canada L8S4L7 (Canada); Song, Wook; Meng, Mei; Kim, Nam Ho; Yoon, Ju-An [Department of Display Engineering, Hoseo University, Sechul-Ri 160, Baebang, Asan, Chung-Nam 336-795 (Korea, Republic of); Kim, Woo Young, E-mail: wykim@hoseo.edu [Department of Display Engineering, Hoseo University, Sechul-Ri 160, Baebang, Asan, Chung-Nam 336-795 (Korea, Republic of); Wood, Richard; Mascher, Peter [Department of Engineering Physics, McMaster University, Hamilton, Ontario, Canada L8S4L7 (Canada)

    2014-02-15

    We investigated the optical properties of light emission based on the resonance energy transfer mechanism between two molecules in the host–dopant systems. For this purpose, we fabricated the organic light-emitting devices with the different doped emissive layers. The host matrices were made of 4,4′,4″-tris(carbasol-l-nyl)triphenylamine (TCTA) and 2-methyl-9,10-di(2-naphthyl)anthracene (MADN) molecules and the doped molecules were 5,6,11,12-tetraphenylnaphtacene (Rubrene) and 4-(Dicyanomethylene)-2-tert-butyl-6- (1,1,7,7-tetramethyljulolidin-4-yl-vinyl)-4H-pyran (DCJTB). The concentrations of the doped molecules were 0.1%, 0.3%, 0.5%, and 0.8%. Through spectroscopic analysis using multi-peak fits with a Gaussian function to the emission spectra, we obtained the relative light intensity of the two dopants according to the doping concentrations and examined the relations between the molecular excited energy states and the nature of energy transfer in the host and dopant systems. We show that the luminous efficiency of the devices has a strong correlation between the energy transfer owing to the individual molecular intrinsic properties and the electrical characteristics associated with the bulky properties in the devices. -- Highlights: • Fabrication and characterization of the OLEDs with a host–dopant system in the emissive layer. • Investigation of the optical properties of light emission based on the resonance energy transfer mechanism between the dopant molecules. • EL and PL spectroscopic study for the structure of the molecular energy levels in the dopant molecules.

  2. Recombination region improvement for reduced efficiency roll-off in phosphorescent OLEDs with dual emissive layers

    Energy Technology Data Exchange (ETDEWEB)

    Ma, Zhu; Zhou, Shunliang [State Key Laboratory of Electronic Thin Films and Integrated Devices, School of Optoelectronic Information, University of Electronic Science and Technology of China (UESTC), Chengdu 610054 (China); Hu, Song [Chengdu Institute of Optics and Electronics, Chinese Academy of Sciences, Chengdu 610209 (China); Yu, Junsheng, E-mail: jsyu@uestc.edu.cn [State Key Laboratory of Electronic Thin Films and Integrated Devices, School of Optoelectronic Information, University of Electronic Science and Technology of China (UESTC), Chengdu 610054 (China)

    2014-10-15

    High-performance phosphorescent organic light-emitting diodes (PhOLEDs) by using dual-emissive-layer (DEL) structure to reduce efficiency roll-off were fabricated. The DEL was comprised of a hole-transport-type host of N, N′-bis(naphthalen-1-yl)-N, N′-bis(phenyl)-benzidine (NPB) and a bipolar host of 4,4′-bis(carbazol-9-yl)biphenyl (CBP), which were both doped with an orange phosphorescent dopant of bis[2-(4-tert-butylphenyl)-benzothiazolato-N,C2′]iridium (acetylacetonate) [(t-bt){sub 2}Ir(acac)]. After the optimization of doping concentration of the first emissive layer (FEL), the device with DEL exhibited 11% lower roll-off power efficiency than single emissive layer devices (SED) when the luminance increased from 1000 cd/m{sup 2} to 10,000 cd/m{sup 2}. The hole–electron recombination zone in DEL was illuminated by inserting an ultrathin fluorescent probe of 4-(dicyanomethylene)-2-tert-butyl-6 (1,1,7,7-tetramethyljulolidin-4-yl-vinyl)-4H-pyran (DCJTB) in different emissive regions. The performance improvement was attributed to the optimization of energy barrier and the expansion of exciton formation zone within the DEL. - Highlights: • PhOLEDs by using a dual-emissive-layer structure to reduce efficiency roll-off were fabricated. • The DED exhibited 11% lower efficiency roll-off, 57% lower turn-on voltage, and 174% higher brightness than SED. • A DCJTB fluorescent probe was inserted at different positions of DED to investigate the expansion of exciton formation zone.

  3. Al/WO{sub 3}/Au as the interconnecting layer for efficient tandem white organic light-emitting diodes

    Energy Technology Data Exchange (ETDEWEB)

    Zhang Hongmei; Dai Yanfeng; Ma Dongge [State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Graduate School of Chinese Academy of Sciences, Changchun 130022 (China)], E-mail: mdg1014@ciac.jl.cn

    2008-05-21

    White light emission from tandem organic light-emitting diodes consisting of blue and red light units separated by a transparent interconnecting layer of Al/WO{sub 3}/Au has been realized. The devices have a structure of indium-tin-oxide (ITO)/molybdenum oxide (MoO{sub 3}) (8 nm)/N, N'-di(naphthalene-1-yl)-N, N'-diphenyl-benzidine (NPB)(100 nm)/p-bis(p-N,N-diphenyl-aminostyryl)benzene) (DSA-ph):2-methyl-9,10-di(2-naphthyl) anthracene (MADN)(40 nm)/tris(8-hydroxylquinoline) aluminium (Alq{sub 3}) (10 nm)/LiF(1 nm)/Al(2 nm)/WO{sub 3}(3 nm)/Au(16 nm)/MoO{sub 3}(5 nm)/NPB(60 nm)/Alq{sub 3}: 4-(dicyanomethylene)-2-t-butyl-6-(1,1,7,7- tetramethyljulolidyl-9-enyl)-4H-pyran (DCJTB)(30 nm)/Alq{sub 3}(30 nm)/LiF(1 nm)/Al(150 nm). It can be seen that a stable white light emission, including 461 and 491 nm peaks from DSA-ph and 620 nm peak from DCJTB, with Commission International De L'Eclairage chromaticity coordinates from (0.35, 0.33) at 8 V to (0.37, 0.30) at 12 V was obtained. The current efficiency and brightness of the white devices are basically equal to the sum of the blue unit and red unit devices. The maximum brightness reached 20 700 cd m{sup -2} at a bias of 23 V, and the maximum current efficiency was 9.1 cd A{sup -1} at a current density of 0.41 mA cm{sup -2}. (fast track communication)

  4. Efficient fluorescent red, green, and blue organic light-emitting devices with a blue host of spirobifluorene derivative

    Energy Technology Data Exchange (ETDEWEB)

    Lee, R.-H. [Department of Chemical and Material Engineering, National Yunlin University of Science and Technology, Yunlin 640, Taiwan (China)], E-mail: lerongho@yuntech.edu.tw; Huang, Y.-W.; Wang, Y.-Y. [Department of Chemical and Material Engineering, National Yunlin University of Science and Technology, Yunlin 640, Taiwan (China); Chang, H.-Y. [EChem Hightech CO., LTD, Hsin-Chu Industrial Park, Hu-Kou, Hsin-Chu, Taiwan (China)

    2008-06-02

    Efficient fluorescent blue, green, and red (RGB) organic light-emitting devices (OLEDs) were fabricated using a blue host material of pyrimidine-containing spirobifluorene derivative 2,7-bis[2-(4-tert-butylphenyl)pyrimidine-5-yl]-9,9'-spirobifluorene (TBPSF) doped with blue dye perylene, green dye 10-(2-benzothiazolyl)-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H, 11H-benzo[l] pyrano[6,7,8-ij] quinolizin-11-one (C545T), and red dye 4-(dicyanomethylene)-2-t-butyl-6-(1,1,7,7-tetramethyljulolidyl-9-enyl) -4H-pyran (DCJTB), respectively. The brightness and current efficiency of the perylene doped blue device reached 10117 cd/m{sup 2} and 2.97 cd/A. Green emission of the C545T doped device reached 8500 cd/m{sup 2} and 13.0 cd/A. Red emission of the DCJTB doped device can be as high as 9000 cd/m{sup 2} and 2.0 cd/A, respectively. High color purity of the blue (Commission Internationale de L'Eclairage (CIE{sub x,y}) coordinates (CIE, x = 0.27, y = 0.24)), green (CIE, x = 0.19, y = 0.63) and red (CIE, x = 0.62, y = 0.37) emissions were achieved for RGB dyes doped TBPSF OLEDs. High brightness, large current efficiency, and good color purity of TBPSF-based RGB OLEDs were obtained by the configuration optimization device, such as inserting the hole and electron-injection materials, and suitable dopant content and light emitting layer thickness.

  5. A study of the compartmentalization of core-shell nanoparticles through fluorescence energy transfer of dopants

    Energy Technology Data Exchange (ETDEWEB)

    Chavez, Jorge L; Jiang Hui; Duran, Randolph S, E-mail: rduran@lsu.edu [Department of Chemistry, University of Florida, PO Box 117200, Gainesville, FL 32611 (United States)

    2010-02-05

    Hybrid organic-inorganic templates and core-shell nanoparticles were used as models to study the communication between fluorescent probes placed inside nanoparticles. The hybrid templates were prepared on the basis of a mixed-surfactant system using octadecyltrimethoxysilane as a reactive amphiphile. The core-shell particles were obtained after coating of the templates with a siloxane shell, using the silanol groups on their surface. Atomic force microscopy imaging showed that the templates were made of a flexible material that flattened significantly after deposition on a substrate and evaporation of the solvent. Pyrene was sequestered by the templates in an aqueous suspension, which placed it in a nonpolar environment, as observed by its fluorescence response. Subsequently, double-doped templates were prepared by sequestering coumarin 153 (C153), with pyrene-doped hybrid templates. The communication between these probes was studied on the basis of their spectral properties, by means of fluorescence resonance energy transfer (FRET). Energy transfer between the dyes with efficiencies up to 55% was observed. Similarly, double-doped core-shell particles prepared on the basis of the hybrid templates were doped with this pair of dyes. Despite the presence of the shell, which was intended to increment the average separation between the probes, interaction of the dyes was observed, although with lower efficiencies. A similar study was performed with C153 and 4-(dicyanomethylene)-2-methyl-6-p-(dimethylamino)styryl-4H-pyran (DCM). FRET studies indicated that the probes were placed in proximity to each other. We confirmed these observations by means of fluorescence lifetime measurements, which showed a decrease in the lifetime of the donor upon addition of the acceptor.

  6. White organic light-emitting diodes from three emitter layers

    Energy Technology Data Exchange (ETDEWEB)

    Kim, M.S. [Department of Advanced Materials Science and Engineering, SungKyunKwan University, Suwon, Gyonggi-Do, 440-746 (Korea, Republic of); Lim, J.T. [Department of Advanced Materials Science and Engineering, SungKyunKwan University, Suwon, Gyonggi-Do, 440-746 (Korea, Republic of); Jeong, C.H. [Department of Advanced Materials Science and Engineering, SungKyunKwan University, Suwon, Gyonggi-Do, 440-746 (Korea, Republic of); Lee, J.H. [Department of Advanced Materials Science and Engineering, SungKyunKwan University, Suwon, Gyonggi-Do, 440-746 (Korea, Republic of); Yeom, G.Y. [Department of Advanced Materials Science and Engineering, SungKyunKwan University, Suwon, Gyonggi-Do, 440-746 (Korea, Republic of)]. E-mail: gyyeom@skku.edu

    2006-11-23

    Three-wavelength white organic light-emitting diodes (WOLEDs) were fabricated using two doped layers, which were obtained by separating the recombination zones into three emitter layers. A sky blue emission originated from the 4,4'-bis(2,2'-diphenylethen-1-yl)biphenyl (DPVBi) layer. A green emission originated from a tris(8-quinolinolato)aluminum (III) (Alq{sub 3}) host doped with a green fluorescent 10-(2-benzothiazolyl)-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-[1] benz opyrano [6,7,8-ij]-quinolizin-11-one (C545T) dye. An orange emission was obtained from the N,N'-bis(1-naphthyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine (NPB) host doped with a red fluorescent dye, 4-(dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetramethyljulolidyl-9-enyl)-4 H-pyran (DCJTB). A white light resulted from the partial excitations of these three emitter layers by controlling the layer thickness and concentration of the fluorescent dyes in each emissive layer simultaneously. The electroluminescent spectrum of the device was not sensitive to the driving voltage of the device. The white light device showed a maximum luminance of approximately 53,000 cd/m{sup 2}. The external quantum and power efficiency at a luminance of approximately 100 cd/m{sup 2} were 2.62% and 3.04 lm/W, respectively.

  7. Improved color purity and efficiency by a coguest emitter system in doped red light-emitting devices

    Energy Technology Data Exchange (ETDEWEB)

    Chen Jiangshan [State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Graduate School of Chinese Academy of Sciences, Changchun 130022 (China); Ma Dongge [State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Graduate School of Chinese Academy of Sciences, Changchun 130022 (China)]. E-mail: mdg1014@ciac.jl.cn

    2007-01-15

    We demonstrate red organic light-emitting diodes (OLEDs) with improved color purity and electroluminescence (EL) efficiency by codoping a green fluorescent sensitizer 10-(2-benzothiazolyl)-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H -(1)-benzopyropyrano(6,7-8-i,j)quinolizin-11-one (C545T) as the second dopant and a red fluorescent dye 4-(dicyanomethylene)-2-t-butyl-6(1,1,7,7-tetramethyljulolidyl-9-enyl) -4H-pyran (DCJTB) as the lumophore into tris(8-hydroquinoline) aluminum (Alq{sub 3}) host. It was found that the C545T dopant did not by itself emit but assisted the carrier trapping from the host Alq{sub 3} to the red emitting dopant. The red OLEDs realized by this approach not only kept the purity of the emission color, but also significantly improved the EL efficiency. The current efficiency and power efficiency, respectively, reached 12cd/A at a current density of 0.3mA/cm{sup 2} and 10lm/W at a current density of 0.02mA/cm{sup 2}, which are enhanced by 1.4 and 2.6 times compared with devices where the emissive layer is composed of the DCJTB doped Alq{sub 3}, and a stable red emission (chromaticity coordinates: x=0.64, y=0.36) was obtained in a wide range of voltage. Our results indicate that the coguest system is a promising method for obtaining high-efficiency red OLEDs.

  8. Surface-plasmon-enhanced lasing emission based on polymer distributed feedback laser

    Energy Technology Data Exchange (ETDEWEB)

    Zhang, Dingke, E-mail: dingke.zhang@gmail.com, E-mail: shijianchen@gmail.com [School of Physics and Electronic Engineering, Chongqing Normal University, Chongqing 401331 (China); Chen, Shijian, E-mail: dingke.zhang@gmail.com, E-mail: shijianchen@gmail.com; Huang, Yingzhou; Zhang, Zhen [School of Physics, Chongqing University, Chongqing 401331 (China); Wang, Yanping; Ma, Dongge [State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022 (China)

    2015-01-14

    Optical losses associated with the metallic contacts necessary for charge injection are an obstacle to the development of electrically pumped organic lasers. In this work, we show that it is possible to overcome these losses by introducing surface plasmons (SPs) in a distributed feedback laser to enhance the lasing emission. We perform a detailed study of the SPs influence on the lasing emission. We experimentally show that enhanced lasing emission has been successfully achieved in the presence of a metal electrode. The laser emission is strongly dependent on the thickness of Ag layer. By optimizing the thickness of Ag layer, surface-plasmon-enhanced lasing emission has been achieved with much reduced thresholds and higher intensity. When the thickness of the Ag layer increases to 50 nm, the device exhibits ten-fold emission intensity and a fifth of excitation threshold comparing with Ag-free one. The finite-difference time-domain (FDTD) results show that large field intensity is built at the 4-(dicyanomethylene)-2-i-propyl-6-(1,1,7,7-tetramethyljulolidyl-9-enyl) -4H-pyran:/poly(9-vinylcarbazole)Ag interface, which could lead to a strong coupling between lasing and SPs, and consequently a much enhanced laser emission at the photon energy of around 2.02 eV (615 nm). Our FDTD simulations gave an explanation of the effects of the SPs on lasing operation in the periodic structures. The use of SPs would lead to a new class of highly efficient solid-state laser sources and provide a new path to achieve electrically pumped organic lasers.

  9. LX4211 increases serum glucagon-like peptide 1 and peptide YY levels by reducing sodium/glucose cotransporter 1 (SGLT1)-mediated absorption of intestinal glucose.

    Science.gov (United States)

    Powell, David R; Smith, Melinda; Greer, Jennifer; Harris, Angela; Zhao, Sharon; DaCosta, Christopher; Mseeh, Faika; Shadoan, Melanie K; Sands, Arthur; Zambrowicz, Brian; Ding, Zhi-Ming

    2013-05-01

    LX4211 [(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triol], a dual sodium/glucose cotransporter 1 (SGLT1) and SGLT2 inhibitor, is thought to decrease both renal glucose reabsorption by inhibiting SGLT2 and intestinal glucose absorption by inhibiting SGLT1. In clinical trials in patients with type 2 diabetes mellitus (T2DM), LX4211 treatment improved glycemic control while increasing circulating levels of glucagon-like peptide 1 (GLP-1) and peptide YY (PYY). To better understand how LX4211 increases GLP-1 and PYY levels, we challenged SGLT1 knockout (-/-) mice, SGLT2-/- mice, and LX4211-treated mice with oral glucose. LX4211-treated mice and SGLT1-/- mice had increased levels of plasma GLP-1, plasma PYY, and intestinal glucose during the 6 hours after a glucose-containing meal, as reflected by area under the curve (AUC) values, whereas SGLT2-/- mice showed no response. LX4211-treated mice and SGLT1-/- mice also had increased GLP-1 AUC values, decreased glucose-dependent insulinotropic polypeptide (GIP) AUC values, and decreased blood glucose excursions during the 6 hours after a challenge with oral glucose alone. However, GLP-1 and GIP levels were not increased in LX4211-treated mice and were decreased in SGLT1-/- mice, 5 minutes after oral glucose, consistent with studies linking decreased intestinal SGLT1 activity with reduced GLP-1 and GIP levels 5 minutes after oral glucose. These data suggest that LX4211 reduces intestinal glucose absorption by inhibiting SGLT1, resulting in net increases in GLP-1 and PYY release and decreases in GIP release and blood glucose excursions. The ability to inhibit both intestinal SGLT1 and renal SGLT2 provides LX4211 with a novel dual mechanism of action for improving glycemic control in patients with T2DM.

  10. Cochliotoxin, a Dihydropyranopyran-4,5-dione, and Its Analogues Produced by Cochliobolus australiensis Display Phytotoxic Activity against Buffelgrass (Cenchrus ciliaris).

    Science.gov (United States)

    Masi, Marco; Meyer, Susan; Clement, Suzette; Cimmino, Alessio; Cristofaro, Massimo; Evidente, Antonio

    2017-05-26

    Buffelgrass (Pennisetum ciliare or Cenchrus ciliaris) is a perennial grass that has become highly invasive in the Sonoran Desert of southern Arizona. In the search for novel control strategies against this weed, strains of the foliar fungal pathogen Cochliobolus australiensis from buffelgrass have been screened for their ability to produce phytotoxic metabolites that could potentially be used as natural herbicides in an integrated pest management strategy. A new phytotoxin, named cochliotoxin, was isolated from liquid culture of this fungus together with radicinin, radicinol, and their 3-epimers. Cochliotoxin was characterized, essentially by spectroscopic methods, as 3-hydroxy-2-methyl-7-(3-methyloxiranyl)-2,3-dihydropyrano[4,3-b]pyran-4,5-dione. Its relative stereochemistry was assigned by 1 H NMR techniques, while the absolute configuration (2S,3S) was determined applying the advanced Mosher's method by esterification of its hydroxy group at C-3. When bioassayed in a buffelgrass coleoptile elongation test and by leaf puncture bioassay against the host weed and two nontarget grasses, cochliotoxin showed strong phytotoxicity. In the same tests, radicinin and 3-epi-radicinin also showed phytotoxic activity, while radicinol and 3-epi-radicinol were largely inactive. All five compounds were more active in leaf puncture bioassays on buffelgrass than on the nontarget grass tanglehead (Heteropogon contortus), while the nontarget grass Arizona cottontop (Digitaria californica) was more sensitive to radicinin and 3-epi-radicinin. Cochliotoxin at low concentration was significantly more active on buffelgrass than on either native grass, but the difference was small.

  11. Transparent organic light-emitting diodes with different bi-directional emission colors using color-conversion capping layers

    International Nuclear Information System (INIS)

    Lee, Jonghee; Koh, Tae-Wook; Cho, Hyunsu; Schwab, Tobias; Lee, Jae-Hyun; Hofmann, Simone; Lee, Jeong-Ik; Yoo, Seunghyup

    2015-01-01

    We report a study on transparent organic light-emitting diodes (OLEDs) with different bi-directional emission colors, enabled by color-conversion organic capping layers. Starting from a transparent blue OLED with an uncapped Ag top electrode exhibiting an average transmittance of 33.9%, a 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran (DCM)-doped tris-(8-hydroxy-quinolinato)-aluminum (Alq3) capping layer is applied to achieve color-conversion from blue to orange-red on the top side while maintaining almost unchanged device transmittance. This color-conversion capping layer does not only change the color of the top side emission, but also enhances the overall device efficiency due to the optical interaction of the capping layer with the primary blue transparent OLED. Top white emission from the transparent bi-directional OLED exhibits a correlated color temperature around 6000–7000 K, with excellent color stability as evidenced by an extremely small variation in color coordinate of Δ(x,y)=(0.002, 0.002) in the forward luminance range of 100–1000 cd m −2 . At the same time, the blue emission color of bottom side is not influenced by the color conversion capping layer, which finally results in different emission colors of the two opposite sides of our transparent OLEDs. - Highlights: • We report transparent organic light-emitting diodes (OLEDs) with different bi-directional emission colors. • Transparent blue OLED with color-conversion organic capping layers (CCL) shows orange top side emission. • Top white emission exhibits a CCT around 7000 K, with excellent color stability on a driving voltage

  12. High color rendering index white organic light-emitting diode using levofloxacin as blue emitter

    Science.gov (United States)

    Miao, Yan-Qin; Gao, Zhi-Xiang; Zhang, Ai-Qin; Li, Yuan-Hao; Wang, Hua; Jia, Hu-Sheng; Liu, Xu-Guang; Tsuboi, Taijuf

    2015-05-01

    Levofloxacin (LOFX), which is well-known as an antibiotic medicament, was shown to be useful as a 452-nm blue emitter for white organic light-emitting diodes (OLEDs). In this paper, the fabricated white OLED contains a 452-nm blue emitting layer (thickness of 30 nm) with 1 wt% LOFX doped in CBP (4,4’-bis(carbazol-9-yl)biphenyl) host and a 584-nm orange emitting layer (thickness of 10 nm) with 0.8 wt% DCJTB (4-(dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetramethyljulolidin-4-yl-vinyl)-4H-pyran) doped in CBP, which are separated by a 20-nm-thick buffer layer of TPBi (2,2’,2”-(benzene-1,3,5-triyl)-tri(1-phenyl-1H-benzimidazole). A high color rendering index (CRI) of 84.5 and CIE chromaticity coordinates of (0.33, 0.32), which is close to ideal white emission CIE (0.333, 0.333), are obtained at a bias voltage of 14 V. Taking into account that LOFX is less expensive and the synthesis and purification technologies of LOFX are mature, these results indicate that blue fluorescence emitting LOFX is useful for applications to white OLEDs although the maximum current efficiency and luminance are not high. The present paper is expected to become a milestone to using medical drug materials for OLEDs. Project supported by the Program for New Century Excellent Talents in University of Ministry of Education of China (Grant No. NCET-13-0927), the International Science & Technology Cooperation Program of China (Grant No. 2012DFR50460), the National Natural Science Foundation of China (Grant Nos. 21101111 and 61274056), and the Shanxi Provincial Key Innovative Research Team in Science and Technology, China (Grant No. 2012041011).

  13. [Multiplayer white organic light-emitting diodes with different order and thickness of emission layers].

    Science.gov (United States)

    Xu, Wei; Lu, Fu-Han; Cao, Jin; Zhu, Wen-Qing; Jiang, Xue-Yin; Zhang, Zhi-Lin; Xu, Shao-Hong

    2008-02-01

    In multilayer OLED devices, the order and thickness of the emission layers have great effect on their spectrum. Based on the three basic colours of red, blue and green, a series of white organic light-emitting diodes(WOLEDS)with the structure of ITO/CuPc(12 nm)/NPB(50 nm)/EML/LiF(1 nm)/Al(100 nm) and a variety of emission layer's orders and thicknesses were fabricated. The blue emission material: 2-t-butyl-9,10-di-(2-naphthyl)anthracene (TBADN) doped with p-bis(p-N, N-diphenyl-amono-styryl)benzene(DSA-Ph), the green emission material: tris-[8-hydroxyquinoline]aluminum(Alq3) doped with C545, and the red emission material: tris-[8-hydroxyquinoline]aluminum( Alq3) doped with 4-(dicyanomethylene)-2-t-butyl-6-(1, 1, 7, 7-tetramethyljulolidyl-9-enyl)-4H-pyran (DCJTB) were used. By adjusting the order and thickness of each emission layer in the RBG structure, we got a white OLED with current efficiency of 5.60 cd x A(-1) and Commission Internationale De L'Eclairage (CIE) coordinates of (0. 34, 0.34) at 200 mA x cm(-2). Its maximum luminance reached 20 700 cd x m(-2) at current density of 400 mA x cm(-2). The results were analyzed on the basis of the theory of excitons' generation and diffusion. According to the theory, an equation was set up which relates EL spectra to the luminance efficiency, the thickness of each layer and the exciton diffusion length. In addition, in RBG structure with different thickness of red layer, the ratio of th e spectral intensity of red to that of blue was calculated. It was found that the experimental results are in agreement with the theoretical values.

  14. Synthesis, spectral, thermal, potentiometric and antimicrobial studies of transition metal complexes of tridentate ligand

    Directory of Open Access Journals (Sweden)

    Sarika M. Jadhav

    2014-01-01

    Full Text Available A series of metal complexes of Cu(II, Ni(II, Co(II, Fe(III and Mn(II have been synthesized with newly synthesized biologically active tridentate ligand. The ligand was synthesized by condensation of dehydroacetic acid (3-acetyl-6-methyl-(2H pyran-2,4(3H-dione or DHA, o-phenylene diamine and fluoro benzaldehyde and characterized by elemental analysis, molar conductivity, magnetic susceptibility, thermal analysis, X-ray diffraction, IR, 1H-NMR, UV–Vis spectroscopy and mass spectra. From the analytical data, the stoichiometry of the complexes was found to be 1:2 (metal:ligand with octahedral geometry. The molar conductance values suggest the non-electrolyte nature of metal complexes. The IR spectral data suggest that the ligand behaves as a dibasic tridentate ligand with ONN donor atoms sequence towards central metal ion. Thermal behaviour (TG/DTA and kinetic parameters calculated by the Coats–Redfern and Horowitz–Metzger method suggest more ordered activated state in complex formation. To investigate the relationship between stability constants of metal complexes and antimicrobial activity, the dissociation constants of Schiff bases and stability constants of their binary metal complexes have been determined potentiometrically in THF–water (60:40% solution at 25 ± 1 °C and at 0.1 M NaClO4 ionic strength. The potentiometric study suggests 1:1 and 1:2 complexation. Antibacterial and antifungal activities in vitro were performed against Staphylococcus aureus, Escherichia coli and Aspergillus niger, Trichoderma, respectively. The stability constants of the metal complexes were calculated by the Irving–Rosotti method. A relation between the stability constant and antimicrobial activity of complexes has been discussed. It is observed that the activity enhances upon complexation and the order of antifungal activity is in accordance with stability order of metal ions.

  15. HARNESSING THE CHEMISTRY OF CO2

    Energy Technology Data Exchange (ETDEWEB)

    Louie, Janis

    2010-05-11

    Our research program is broadly focused on activating CO{sub 2} through the use of organic and organometallic based catalysts. Some of our methods have centered on annulation reactions of unsaturated hydrocarbons (and carbonyl substrates) to provide a diverse array of carbocycles and heterocycles. We use a combination of catalyst discovery and optimization in conjunction with classical physical organic chemistry to elucidate the key mechanistic features of the cycloaddition reactions such that the next big advances in catalyst development can be made. Key to all of our cycloaddition reactions is the use of a sterically hindered, electron donating N heterocyclic carbene (NHC) ligand, namely IPr (or SIPr), in conjunction with a low valent nickel pre-catalyst. The efficacy of this ligand is two-fold: (1) the high {delta}-donating ability of the NHC increases the nucleophilicity of the metal center which thereby facilitates interaction with the electrophilic carbonyl and (2) the steric hindrance prevents an otherwise competitive side reaction involving only the alkyne substrate. Such a system has allowed for the facile cycloaddition to prepare highly functionalized pyrones, pyridones, pyrans, as well as novel carbocycles. Importantly, all reactions proceed under extremely mild conditions (room temperature, atmospheric pressures, and short reaction times), require only catalytic amounts of Ni/NHC and readily available starting materials, and afford annulated products in excellent yields. Our current focus revolves around understanding the fundamental processes that govern these cycloadditions such that the next big advance in the cyclization chemistry of CO{sub 2} can be made. Concurrent to our annulation chemistry is our investigation of the potential for imidazolylidenes to function as thermally-actuated CO{sub 2} sequestering and delivery agents.

  16. Pyranopterin Coordination Controls Molybdenum Electrochemistry in Escherichia coli Nitrate Reductase.

    Science.gov (United States)

    Wu, Sheng-Yi; Rothery, Richard A; Weiner, Joel H

    2015-10-09

    We test the hypothesis that pyranopterin (PPT) coordination plays a critical role in defining molybdenum active site redox chemistry and reactivity in the mononuclear molybdoenzymes. The molybdenum atom of Escherichia coli nitrate reductase A (NarGHI) is coordinated by two PPT-dithiolene chelates that are defined as proximal and distal based on their proximity to a [4Fe-4S] cluster known as FS0. We examined variants of two sets of residues involved in PPT coordination: (i) those interacting directly or indirectly with the pyran oxygen of the bicyclic distal PPT (NarG-Ser(719), NarG-His(1163), and NarG-His(1184)); and (ii) those involved in bridging the two PPTs and stabilizing the oxidation state of the proximal PPT (NarG-His(1092) and NarG-His(1098)). A S719A variant has essentially no effect on the overall Mo(VI/IV) reduction potential, whereas the H1163A and H1184A variants elicit large effects (ΔEm values of -88 and -36 mV, respectively). Ala variants of His(1092) and His(1098) also elicit large ΔEm values of -143 and -101 mV, respectively. An Arg variant of His(1092) elicits a small ΔEm of +18 mV on the Mo(VI/IV) reduction potential. There is a linear correlation between the molybdenum Em value and both enzyme activity and the ability to support anaerobic respiratory growth on nitrate. These data support a non-innocent role for the PPT moieties in controlling active site metal redox chemistry and catalysis. © 2015 by The American Society for Biochemistry and Molecular Biology, Inc.

  17. Pyranopterin Coordination Controls Molybdenum Electrochemistry in Escherichia coli Nitrate Reductase*

    Science.gov (United States)

    Wu, Sheng-Yi; Rothery, Richard A.; Weiner, Joel H.

    2015-01-01

    We test the hypothesis that pyranopterin (PPT) coordination plays a critical role in defining molybdenum active site redox chemistry and reactivity in the mononuclear molybdoenzymes. The molybdenum atom of Escherichia coli nitrate reductase A (NarGHI) is coordinated by two PPT-dithiolene chelates that are defined as proximal and distal based on their proximity to a [4Fe-4S] cluster known as FS0. We examined variants of two sets of residues involved in PPT coordination: (i) those interacting directly or indirectly with the pyran oxygen of the bicyclic distal PPT (NarG-Ser719, NarG-His1163, and NarG-His1184); and (ii) those involved in bridging the two PPTs and stabilizing the oxidation state of the proximal PPT (NarG-His1092 and NarG-His1098). A S719A variant has essentially no effect on the overall Mo(VI/IV) reduction potential, whereas the H1163A and H1184A variants elicit large effects (ΔEm values of −88 and −36 mV, respectively). Ala variants of His1092 and His1098 also elicit large ΔEm values of −143 and −101 mV, respectively. An Arg variant of His1092 elicits a small ΔEm of +18 mV on the Mo(VI/IV) reduction potential. There is a linear correlation between the molybdenum Em value and both enzyme activity and the ability to support anaerobic respiratory growth on nitrate. These data support a non-innocent role for the PPT moieties in controlling active site metal redox chemistry and catalysis. PMID:26297003

  18. Development of [11C]/[3H]THK-5351 – A potential novel carbon-11 tau imaging PET radioligand

    International Nuclear Information System (INIS)

    Stepanov, Vladimir; Svedberg, Marie; Jia, Zhisheng; Krasikova, Raisa; Lemoine, Laetitia; Okamura, Nobujuki; Furumoto, Shozo; Mitsios, Nicholas; Mulder, Jan; Långström, Bengt; Nordberg, Agneta; Halldin, Christer

    2017-01-01

    Introduction: Due to the rise in the number of patients with dementia the imperative for finding new diagnostic and treatment options becomes ever more pressing. While significant progress has been made in PET imaging of Aβ aggregates both in vitro and in vivo, options for imaging tau protein aggregates selectively are still limited. Based on the work previously published by researchers from the Tohoku University, Japan, that resulted in the development of [ 18 F]THK-5351, we have undertaken an effort to develop a carbon-11 version of the identical structure - [ 11 C]THK-5351. In parallel, THK-5351 was also labeled with tritium ([ 3 H]THK-5351) for use in in vitro autoradiography (ARG). Methods: The carbon-11 labeling was performed starting with di-protected enantiomeric pure precursor - tert-butyl 5-(6-((2S)-3-fluoro-2-(tetrahydro-2H-pyran-2-yloxy)propoxy)quinolin-2-yl) pyridin-2-yl carbamate, which was reacted with [ 11 C]MeI, using DMF as the solvent and NaH as base, followed by deprotection with trifluoroacetic acid/water mixture, resulting in enantiomerically pure carbon-11 radioligand, [ 11 C]THK-5351 - (S)-1-fluoro-3-(2-(6-([ 11 C]methylamino)pyridin-3-yl)quinolin-6-yloxy) propan-2-ol. Tritium labeling and purification of [ 3 H]THK-5351 were undertaken using similar approach, resulting in [ 3 H]THK-5351 with RCP >99.8% and specific radioactivity of 1.3 GBq/μmol. Results: [ 11 C]THK-5351 was produced in good yield (1900 ± 355 MBq), specific radioactivity (SRA) (361 ± 119 GBq/μmol at EOS + 20 min) and radiochemical purity (RCP) (>99.8%), with enantiomeric purity of 98.7%. [ 3 H]THK-5351 was evaluated for ARG of tau binding in post-mortem human brain tissue using cortical sections from one AD patient and one control subject. [ 3 H]THK-5351 binding density was higher in the AD patient compared to the control subject, the binding was displaced by unlabeled THK-5351 confirming specific [ 3 H]THK-5351 binding.

  19. The effects of Ficus carica on the activity of enzymes related to metabolic syndrome

    Directory of Open Access Journals (Sweden)

    Ramgopal Mopuri

    2018-01-01

    Full Text Available The present study aimed to investigate the effects of the various parts of Ficus carica L. (figs on antioxidant, antidiabetic, and antiobesogenic effects in vitro. Fruit, leaves, and stembark of the F. carica plant were sequentially extracted using organic and inorganic solvents and their total polyphenol and flavonoid contents were estimated. The effects of the extracts on antioxidative, antidiabetic (inhibition of α-amylase and α-glucosidase enzymes, and antiobesogenic (antilipase activities were measured using several experimental models. The fruit ethanolic extract contained a high quantity of polyphenols and flavonoids (104.67±5.51 μg/mL and 81.67±4.00 μg/mL compared with all other extracts. The activity of the ethanolic extract of F. carica fruit was significantly (p<0.05 higher than all other extracts and parts of the plant in terms of antioxidative, antidiabetic, and antiobesogenic effects. The IC50 values of the fruit ethanolic extract in terms of antioxidative (134.44±18.43 μg/mL, and inhibition of α-glucosidase (255.57±36.46 μg/mL, α-amylase (315.89±3.83 μg/mL, and pancreatic lipase (230.475±9.65 μg/mL activity indicate that the activity of fruit ethanolic extract is better than all other extracts of the plant. The gas chromatography–mass spectroscopy analysis of the fruit ethanolic extract showed the presence of a number of bioactive compounds such as butyl butyrate, 5-hydroxymethyl furfural, 1-butoxy-1-isobutoxy butane, malic acid, tetradecanoic acid, phytol acetate, trans phytol, n-hexadecanoic acid, 9Z,12Z-octadecadienoic acid, stearic acid, sitosterol, 3,5-dihydroxy-6-methyl-2,3-dihydro-4H-pyran-4-one, and 2,4,5-trimethyl-2,4-dihydro-3H-pyrazol-3-one. The results of this study suggest that the ethanolic extract of the fruit of F. carica may have potential antidiabetic and antiobesogenic agents.

  20. Thermal decomposition of specifically phosphorylated D-glucoses and their role in the control of the Maillard reaction.

    Science.gov (United States)

    Yaylayan, Varoujan A; Machiels, David; Istasse, Louis

    2003-05-21

    One of the main shortcomings of the information available on the Maillard reaction is the lack of knowledge to control the different pathways, especially when it is desired to direct the reaction away from the formation of carcinogenic and other toxic substances to more aroma and color generation. The use of specifically phosphorylated sugars may impart some elements of control over the aroma profile generated by the Maillard reaction. Thermal decomposition of 1- and 6-phosphorylated glucoses was studied in the presence and absence of ammonia and selected amino acids through pyrolysis/gas chromatography/mass spectrometry using nonpolar PLOT and medium polar DB-1 columns. The analysis of the data has indicated that glucose-1-phosphate relative to glucose undergoes more extensive phosphate-catalyzed ring opening followed by formation of sugar-derived reactive intermediates as was indicated by a 9-fold increase in the amount of trimethylpyrazine and a 5-fold increase in the amount of 2,3-dimethylpyrazine, when pyrolyzed in the presence of glycine. In addition, glucose-1-phosphate alone generated a 6-fold excess of acetol as compared to glucose. On the other hand, glucose-6-phosphate enhanced retro-aldol reactions initiated from a C-6 hydroxyl group and increased the subsequent formation of furfural and 4-cyclopentene-1,3-dione. Furthermore, it also stabilized 1- and 3-deoxyglucosone intermediates and enhanced the formation of six carbon atom-containing Maillard products derived directly from them through elimination reactions such as 1,6-dimethyl-2,4-dihydroxy-3-(2H)-furanone (acetylformoin), 2-acetylpyrrole, 5-methylfurfural, 5-hydroxymethylfurfural, and 4-hydroxy-2,5-dimethyl-3-(2H)-furanone (Furaneol), due to the enhanced leaving group ability of the phosphate moiety at the C-6 carbon. However, Maillard products generated through the nucleophilic action of the C-6 hydroxyl group such as 2-acetylfuran and 2,3-dihydro-3,5-dihydroxy-4H-pyran-4-one were retarded, due

  1. Quantitative determination of sotolon, maltol and free furaneol in wine by solid-phase extraction and gas chromatography-ion-trap mass spectrometry.

    Science.gov (United States)

    Ferreira, Vicente; Jarauta, Idoia; López, Ricardo; Cacho, Juan

    2003-08-22

    A method for the analytical determination of sotolon [4,5-dimethyl-3-hydroxy-2(5H)-furanone], maltol [3-hydroxy-2-methyl-4H-pyran-4-one] and free furaneol [2,5-dimethyl-4-hydroxy-3(2H)-furanone] in wine has been developed. The analytes are extracted from 50 ml of wine in a solid-phase extraction cartridge filled with 800 mg of LiChrolut EN resins. Interferences are removed with 15 ml of a pentane-dichloromethane (20:1) solution, and analytes are recovered with 6 ml of dichloromethane. The extract is concentrated up to 0.1 ml and analyzed by GC-ion trap MS. Maltol and sotolon were determined by selected ion storage of ions in the m/z ranges 120-153 and 79-95, using the ions m/z 126 and 83 for quantitation, respectively. Furaneol was determined by non-resonant fragmentation of the m/z 128 mother ion and subsequent analysis of the m/z 81 ion. The detection limits of the method are in all cases between 0.5 and 1 microg l(-1), well below the olfactory thresholds of the compounds. The precision of the method is in the 4-5% range for levels in wine around 20 microg l(-1). Linearity holds at least up to 400 microg l(-1), and is satisfactory in all cases. The recoveries of maltol and sotolon are constant (70 and 64%, respectively) and do not depend on the type of wine. On the contrary, in the case of furaneol, red wines show constant and high recoveries (97%), while the recoveries on white wines range between 30 and 80%. Different experiments showed that this behavior is probably due to the existence of complexes formed between furaneol and sulphur dioxide or catechols. Sensory experiments confirmed that the complexed forms found in white wines are not perceived by orthonasal olfaction, and that the furaneol determined by the method can be considered as the free and odor-active fraction.

  2. Characterization of the aroma profile of Madeira wine by sorptive extraction techniques.

    Science.gov (United States)

    Alves, R F; Nascimento, A M D; Nogueira, J M F

    2005-08-01

    The characterization of the aroma profile of 33 samples of Madeira wine from five monovarieties (Sercial, Verdelho, Boal, Malvasia and Tinta Negra Mole) having different type and categories is presented, using solid phase microextraction and stir bar sorptive extraction techniques (SPME and SBSE) followed by capillary gas chromatography and mass spectrometry detection (GC-MS). Headspace SPME/GC-MS provided effectiveness to identify the major constituents of the aroma profile of Madeira wine, where no remarkable differences occur among the samples studied. The volatile compounds are mainly constituted by ethyl octanoate (11.3-256.9μgL -1 ), ethyl decanoate (21.5-210.5μgL -1 ), ethyl decenoate (0.1-112.8μgL -1 ), diethyl succinate (0.9-65.6μgL -1 ), ethyl dodecanoate (1.2-6.5μgL -1 ), ethyl nonanoate (0.6-5.2μgL -1 ), ethyl hexanoate (0.2-3.7μgL -1 ) and isoamyl octanoate (0-2.2μgL -1 ). C 13 norisoprenoids such as vitispirane (0.9-7.0μgL -1 ) and 1,1,6-trimethyl 1,2-dihydro naphthalene (0.7-12.5μgL -1 ), as well as phenyl ethanol (0-8.1μgL -1 ), were also found in Madeira wine samples. The powerful capabilities of SBSE followed thermal desorption and GC-MS analysis allowed higher ability for profiling traces and ultra traces of compounds in Madeira wine samples, including esters (80.7-89.7%), carboxylic acids (1.6-4.2%), alcohols (3.5-8.2%), aldehydes (0.9-3.7%), pyrans (0.2-1.7%), lactones (sensorial threshold limits. Excellent correlation between Madeira wine ageing and the abundance of cis-oak lactone was attained showing to be an important chemical descriptor to characterize reserves and Vintages as well as a contributor to wine flavour. The differentiation between reserves, dry/medium dry and sweet/medium sweet young wines could be well established by means of chemometric analysis, using particular aroma compounds such as diethyl succinate, cis-oak lactone and ethyl octanoate as discriminating variables.

  3. Materials Design via Optimized Intramolecular Noncovalent Interactions for High-Performance Organic Semiconductors

    Energy Technology Data Exchange (ETDEWEB)

    Guo, Xiaojie; Liao, Qiaogan; Manley, Eric F.; Wu, Zishan; Wang, Yulun; Wang, Weida; Yang, Tingbin; Shin, Young-Eun; Cheng, Xing; Liang, Yongye; Chen, Lin X.; Baeg, Kang-Jun; Marks, Tobin J.; Guo, Xugang

    2016-03-15

    We report the design, synthesis, and implemention in semiconducting polymers of a novel head-to-head linkage containing the TRTOR (3-alkyl-3'-alkoxy-2,2'-bithiophene) donor subunit having a single strategically optimized, planarizing noncovalent S···O interaction. Diverse complementary thermal, optical, electrochemical, X-ray scattering, electrical, photovoltaic, and electron microscopic characterization techniques are applied to establish structure-property correlations in a TRTOR-based polymer series. In comparison to monomers having double S···O interactions, replacing one alkoxy substituent with a less electron-donating alkyl one yields TRTOR-based polymers with significantly depressed (0.2-0.3 eV) HOMOs. Furthermore, the weaker single S···O interaction and greater TRTOR steric encumberance enhances materials processability without sacrificing backbone planarity. From another perspective, TRTOR has comparable electronic properties to ring-fused 5Hdithieno[ 3,2-b:2',3'-d]pyran (DTP) subunits, but a centrosymmetric geometry which promotes a more compact and ordered structure than bulkier, axisymmetric DTP. Compared to monosubstituted TTOR (3-alkoxy-2,2'-bithiophene), alkylation at the TRTOR bithiophene 3-position enhances conjugation and polymer crystallinity with contracted π-π stacking. Grazing incidence wide-angle X-ray scattering (GIWAXS) data reveal that the greater steric hindrance and the weaker single S···O interaction are not detrimental to close packing and high crystallinity. As a proof of materials design, copolymerizing TRTOR with phthalimides yields copolymers with promising thin-film transistor mobility as high as 0.42 cm2/(V·s) and 6.3% power conversion efficiency in polymer solar cells, the highest of any phthalimide copolymers reported to date. The depressed TRTOR HOMOs imbue these polymers with substantially increased Ion/Ioff ratios and Voc’s versus analogous subunits with multiple electron donating

  4. Comparison of germination responses of Anigozanthos flavidus (Haemodoraceae), Gyrostemon racemiger and Gyrostemon ramulosus (Gyrostemonaceae) to smoke-water and the smoke-derived compounds karrikinolide (KAR1) and glyceronitrile.

    Science.gov (United States)

    Downes, Katherine S; Light, Marnie E; Pošta, Martin; Kohout, Ladislav; van Staden, Johannes

    2013-03-01

    A major germination-promoting chemical in smoke-water is 3-methyl-2H-furo[2,3-c]pyran-2-one (karrikinolide, KAR(1)). However, not all species that germinate in response to smoke-water are responsive to KAR(1), such as Tersonia cyathiflora (Gyrostemonaceae). In this study, a test was made of whether two Gyrostemon species (Gyrostemonaceae) that have previously been shown to respond to smoke-water, respond to KAR(1). If not, then the smoke-derived chemical that stimulates germination of these species is currently unknown. Recently, glyceronitrile was isolated from smoke-water and promoted the germination of certain Anigozanthos species (Haemodoraceae). Whether this chemical promotes Gyrostemon racemiger germination is also examined. Furthermore, an investigation was carried out into whether these species germinate in response to smoke-water derived from burning cellulose alone. Gyrostemon racemiger and G. ramulosus seeds were buried after collection and retrieved in autumn the following year when dormancy was alleviated and seeds had become responsive to smoke-water. Anigozanthos flavidus seeds were after-ripened at 35 °C to alleviate dormancy. Gyrostemon and Anigozanthos seeds were then tested with 'Seed Starter' smoke-water, KAR(1), glyceronitrile and cellulose-derived smoke-water. Although Gyrostemon racemiger, G. ramulosus and A. flavidus were all stimulated to germinate by 'Seed Starter' smoke-water, none of these species responded to KAR(1). Gyrostemon racemiger germination was not promoted by glyceronitrile. This is in contrast to A. flavidus, where glyceronitrile, at concentrations of 1-500 µm, promoted germination, although seedling growth was inhibited at ≥400 µm. Maximum A. flavidus germination occurred at glyceronitrile concentrations of 25-300 µm. Some Gyrostemon germination was promoted by cellulose-derived smoke-water. KAR(1) and glyceronitrile, chemicals in smoke-water that are known to stimulate germination in other species, did not promote the

  5. Photoluminescence and electroluminescence of a novel green-yellow emitting material-5,6-Bis-[4-(naphthalene-1-yl-phenyl-amino)-phenyl] -pyrazine-2,3-dicarbonitrile

    International Nuclear Information System (INIS)

    Chew Siewling; Wang Pengfei; Hong Zirou; Kwong, H.L.; Tang Jianxin; Sun Shiling; Lee, C.S.; Lee, S.-T.

    2007-01-01

    A new compound with intramolecular charge transfer (ICT) property-5,6-Bis-[4-(naphthalene-1-yl-phenyl-amino)-phenyl] -pyrazine-2,3-dicarbonitrile(BNPPDC) was synthesized. The new compound was strongly fluorescent in non-polar and moderately polar solvents, as well as in thin solid film. The absorption and emission maxima shifted to longer wavelength with increasing solvent polarity. The fluorescence quantum yield also increased with increasing solvent polarity from non-polar to moderately polar solvents, then decreased with further increase of solvent polarity. This indicates both 'positive' and 'negative' solvatokinetic effects co-existed. Using this material as hole-transporting emitter and host emitter, we fabricated two electroluminescent (EL) devices with structures of A (ITO/BNPPDC (45 nm)/1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI) (45 nm)/Mg:Ag (200 nm) and B (ITO/N,N'-diphenyl-N,N'-bis-(3-methylphenyl) (1,1'-diphenyl)4,4'-diamine (TPD) (50 nm)/BNPPDC (20 nm)/1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI) (45 nm)/Mg:Ag (200 nm). The devices showed green-yellow EL emission with good efficiency and high brightness. For example, the device A exhibited a high brightness of 17400 cd/m 2 at a driving voltage of 11 V and a very low turn-on voltage (2.9 V), as well as a maximum luminous efficiency 3.61 cd/A. The device B showed a similar performance with a high brightness of 12650 cd/m 2 at a driving voltage of 13 V and a maximum luminous efficiency 3.62 cd/A. In addition, the EL devices using BNPPDC as a host and 4-(dicyanomethylene)-2-t-butyl-6-(1,1,7,7-tetramethyljulolidyl-9-enyl) -4H-pyran (DCJTB) as a dopant (configuration: ITO/TPD (60 nm)/BNPPDC:DCJTB (2%) (30 nm)/TPBI (35 nm)/Mg:Ag (200 nm)) showed a good performance with a brightness of 150 cd/m 2 at 4.5 V, a maximum brightness of 12600 cd/m 2 at 11.5 V, and a maximum luminous efficiency of 3.30 cd/A

  6. Materials Design via Optimized Intramolecular Noncovalent Interactions for High-Performance Organic Semiconductors

    Energy Technology Data Exchange (ETDEWEB)

    Guo, Xiaojie [Shenzhen Key Laboratory; Liao, Qiaogan [Shenzhen Key Laboratory; Manley, Eric F. [Department; Chemical; Wu, Zishan [Shenzhen Key Laboratory; Wang, Yulun [Shenzhen Key Laboratory; Wang, Weida [Shenzhen Key Laboratory; Yang, Tingbin [Shenzhen Key Laboratory; Shin, Young-Eun [Department; Cheng, Xing [Shenzhen Key Laboratory; Liang, Yongye [Shenzhen Key Laboratory; Chen, Lin X. [Department; Chemical; Baeg, Kang-Jun [Department; Marks, Tobin J. [Department; Guo, Xugang [Shenzhen Key Laboratory

    2016-03-15

    We report the design, synthesis, and implemention in semiconducting polymers of a novel head-to-head linkage containing the TRTOR (3-alkyl-3'-alkoxy-2,2'-bithiophene) donor subunit having a single strategically optimized, planarizing noncovalent S···O interaction. Diverse complementary thermal, optical, electrochemical, X-ray scattering, electrical, photovoltaic, and electron microscopic characterization techniques are applied to establish structure–property correlations in a TRTOR-based polymer series. In comparison to monomers having double S···O interactions, replacing one alkoxy substituent with a less electron-donating alkyl one yields TRTOR-based polymers with significantly depressed (0.2–0.3 eV) HOMOs. Furthermore, the weaker single S···O interaction and greater TRTOR steric encumberance enhances materials processability without sacrificing backbone planarity. From another perspective, TRTOR has comparable electronic properties to ring-fused 5H-dithieno[3,2-b:2',3'-d]pyran (DTP) subunits, but a centrosymmetric geometry which promotes a more compact and ordered structure than bulkier, axisymmetric DTP. Compared to monosubstituted TTOR (3-alkoxy-2,2'-bithiophene), alkylation at the TRTOR bithiophene 3-position enhances conjugation and polymer crystallinity with contracted π–π stacking. Grazing incidence wide-angle X-ray scattering (GIWAXS) data reveal that the greater steric hindrance and the weaker single S···O interaction are not detrimental to close packing and high crystallinity. As a proof of materials design, copolymerizing TRTOR with phthalimides yields copolymers with promising thin-film transistor mobility as high as 0.42 cm2/(V·s) and 6.3% power conversion efficiency in polymer solar cells, the highest of any phthalimide copolymers reported to date. The depressed TRTOR HOMOs imbue these polymers with substantially increased Ion/Ioff ratios and Voc’s versus analogous subunits with multiple electron

  7. Dependence of surface morphology on molecular structure and its influence on the properties of OLEDs

    Energy Technology Data Exchange (ETDEWEB)

    Lim, S.H. [Department of Chemical Engineering, Hongik University, 72-1, Sangsu-Dong, Mapo-Gu, Seoul 121-791 (Korea, Republic of); Ryu, G.Y. [Department of Electric Information and Control Engineering, Hongik University, 72-1, Sangsu-Dong, Mapo-Gu, Seoul 121-791 (Korea, Republic of); Seo, J.H.; Park, J.H. [Center for Organic Materials and Information Devices (COMID), Hongik University, 72-1, Sangsu-Dong, Mapo-Gu, Seoul 121-791 (Korea, Republic of); Department of Information Display, Hongik University, 72-1, Sangsu-Dong, Mapo-Gu, Seoul 121-791 (Korea, Republic of); Youn, S.W. [Department of Chemical Engineering, Hongik University, 72-1, Sangsu-Dong, Mapo-Gu, Seoul 121-791 (Korea, Republic of); Kim, Y.K. [Center for Organic Materials and Information Devices (COMID), Hongik University, 72-1, Sangsu-Dong, Mapo-Gu, Seoul 121-791 (Korea, Republic of); Department of Information Display, Hongik University, 72-1, Sangsu-Dong, Mapo-Gu, Seoul 121-791 (Korea, Republic of); Shin, D.M. [Department of Chemical Engineering, Hongik University, 72-1, Sangsu-Dong, Mapo-Gu, Seoul 121-791 (Korea, Republic of)], E-mail: shindm@wow.hongik.ac.kr

    2008-09-15

    Most organic light-emitting diodes (OLEDs) have a multilayer structure composed of organic layers such as a hole injection layer (HIL), a hole transport layer (HTL), an emission layer (EML), an electron transport layer (ETL) and an electron injection layer (EIL) sandwiched between two electrodes. The organic layers are thin solid films with a thickness from a few nano meters to a few tenths nano meter, respectively. Surface morphology of an organic thin solid film in OLEDs depends on the molecular structure of the organic material and has an affect on device performance. To analyze the effect of surface morphology of an organic thin solid film on fluorescence and electroluminescence (EL) properties, thin solid films of 4-(dicyanomethylene)-2-methyl-6-(julolidin-4-yl-vinyl)-4H-pyran (DCM2) and new red fluorophores, (2E,2'E)-3,3'-[4,4''-bis(dimethylamino)-1,1':4',1''-terphenyl-2',5'-diyl] bis[2= -(2-thienyl)acrylonitrile] (ABCV-Th) and (2Z,2'Z)-3,3'-[4,4''-bis(dimethylamino)-1,1':4',1''-terphenyl-2',5'-diyl] bis(2-phenylacrylonitrile) (ABCV-P) were investigated by atomic force microscopy (AFM). The samples for EL and AFM measurement were fabricated by the high-vacuum thermal deposition (8x10{sup -7} Torr) of organic materials onto the surface of indium tin oxide (ITO)-coated glass substrate, in which the layer structures of samples for AFM measurement and those for EL measurement were ITO/NPB (40 nm)/red emitters (80 nm) and ITO/NPB (40 nm)/red emitters (80 nm)/BCP (30 nm)/Liq (2 nm)/Al (100 nm), respectively. The analysis based on AFM measurements well supported that the photoluminescence properties and the device performance were very much dependent upon surface morphology of an organic thin layer.

  8. Photoluminescence and electroluminescence of a novel green-yellow emitting material-5,6-Bis-[4-(naphthalene-1-yl-phenyl-amino)-phenyl] -pyrazine-2,3-dicarbonitrile

    Energy Technology Data Exchange (ETDEWEB)

    Chew Siewling [Center of Super-Diamond and Advanced Films (COSDAF) and Department of Physics and Materials Science, City University of Hong Kong, Hong Kong (China); Wang Pengfei [Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100101 (China)]. E-mail: wangpf@mail.ipc.ac.cn; Hong Zirou [Center of Super-Diamond and Advanced Films (COSDAF) and Department of Physics and Materials Science, City University of Hong Kong, Hong Kong (China); Kwong, H.L. [Department of Biology and Chemistry, City University of Hong Kong, Hong Kong (China); Tang Jianxin [Center of Super-Diamond and Advanced Films (COSDAF) and Department of Physics and Materials Science, City University of Hong Kong, Hong Kong (China); Sun Shiling [Center of Super-Diamond and Advanced Films (COSDAF) and Department of Physics and Materials Science, City University of Hong Kong, Hong Kong (China); Lee, C.S. [Center of Super-Diamond and Advanced Films (COSDAF) and Department of Physics and Materials Science, City University of Hong Kong, Hong Kong (China)]. E-mail: apcslee@cityu.edu.hk; Lee, S.-T. [Center of Super-Diamond and Advanced Films (COSDAF) and Department of Physics and Materials Science, City University of Hong Kong, Hong Kong (China)]. E-mail: apannale@cityu.edu.hk

    2007-06-15

    A new compound with intramolecular charge transfer (ICT) property-5,6-Bis-[4-(naphthalene-1-yl-phenyl-amino)-phenyl] -pyrazine-2,3-dicarbonitrile(BNPPDC) was synthesized. The new compound was strongly fluorescent in non-polar and moderately polar solvents, as well as in thin solid film. The absorption and emission maxima shifted to longer wavelength with increasing solvent polarity. The fluorescence quantum yield also increased with increasing solvent polarity from non-polar to moderately polar solvents, then decreased with further increase of solvent polarity. This indicates both 'positive' and 'negative' solvatokinetic effects co-existed. Using this material as hole-transporting emitter and host emitter, we fabricated two electroluminescent (EL) devices with structures of A (ITO/BNPPDC (45 nm)/1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI) (45 nm)/Mg:Ag (200 nm) and B (ITO/N,N'-diphenyl-N,N'-bis-(3-methylphenyl) (1,1'-diphenyl)4,4'-diamine (TPD) (50 nm)/BNPPDC (20 nm)/1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI) (45 nm)/Mg:Ag (200 nm). The devices showed green-yellow EL emission with good efficiency and high brightness. For example, the device A exhibited a high brightness of 17400 cd/m{sup 2} at a driving voltage of 11 V and a very low turn-on voltage (2.9 V), as well as a maximum luminous efficiency 3.61 cd/A. The device B showed a similar performance with a high brightness of 12650 cd/m{sup 2} at a driving voltage of 13 V and a maximum luminous efficiency 3.62 cd/A. In addition, the EL devices using BNPPDC as a host and 4-(dicyanomethylene)-2-t-butyl-6-(1,1,7,7-tetramethyljulolidyl-9-enyl) -4H-pyran (DCJTB) as a dopant (configuration: ITO/TPD (60 nm)/BNPPDC:DCJTB (2%) (30 nm)/TPBI (35 nm)/Mg:Ag (200 nm)) showed a good performance with a brightness of 150 cd/m{sup 2} at 4.5 V, a maximum brightness of 12600 cd/m{sup 2} at 11.5 V, and a maximum luminous efficiency of 3.30 cd/A.

  9. A Novel trans-1-(9-Anthryl)-2-phenylethene Derivative Containing a Phenanthroimidazole Unit for Application in Organic Light-Emitting Diodes.

    Science.gov (United States)

    Zhou, Nonglin; Wang, Shirong; Xiao, Yin; Li, Xianggao

    2018-01-04

    Aryl-substituted phenanthroimidazoles (PIs) have attracted tremendous attention in the field of organic light-emitting diodes (OLEDs), because they are simple to synthesize and have excellent thermal properties, high photoluminescence quantum yields (PLQYs), and bipolar properties. Herein, a novel blue-green emitting material, (E)-2-{4'-[2-(anthracen-9-yl)vinyl]-[1,1'-biphenyl]-4-yl}-1-phenyl-1H-phenanthro[9,10-d]imidazole (APE-PPI), containing a t-APE [1-(9-anthryl)-2-phenylethene] core and a PI moiety was designed and synthesized. Owing to the PI skeleton, APE-PPI possesses high thermal stability and a high PLQY, and the compound exhibits bipolar transporting characteristics, which were identified by single-carrier devices. Nondoped blue-green OLEDs with APE-PPI as the emitting layer show emission at λ=508 nm, a full width at half maximum of 82 nm, a maximum brightness of 9042 cd m -2 , a maximum current efficiency of 2.14 cd A -1 , and Commission Internationale de L'Eclairage (CIE) coordinates of (0.26, 0.55). Furthermore, a white OLED (WOLED) was fabricated by employing APE-PPI as the blue-green emitting layer and 4-(dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetramethyljulolidin-4-yl-vinyl)-4H-pyran (DCJTB) doped in tris-(8-hydroxyquinolinato)aluminum (Alq 3 ) as the red-green emitting layer. This WOLED exhibited a maximum brightness of 10029 cd m -2 , a maximum current efficiency of 16.05 cd A -1 , CIE coordinates of (0.47, 0.47), and a color rendering index (CRI) of 85. The high performance of APE-PPI-based devices suggests that the t-APE and PI combination can potentially be used to synthesize efficient electroluminescent materials for WOLEDs. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  10. Inhibiting Heat-Shock Protein 90 Reverses Sensory Hypoalgesia in Diabetic Mice

    Directory of Open Access Journals (Sweden)

    Michael J Urban

    2010-07-01

    Full Text Available Increasing the expression of Hsp70 (heat-shock protein 70 can inhibit sensory neuron degeneration after axotomy. Since the onset of DPN (diabetic peripheral neuropathy is associated with the gradual decline of sensory neuron function, we evaluated whether increasing Hsp70 was sufficient to improve several indices of neuronal function. Hsp90 is the master regulator of the heat-shock response and its inhibition can up-regulate Hsp70. KU-32 (N-{7-[(2R, 3R, 4S, 5R-3, 4-dihydroxy-5-methoxy-6, 6-dimethyl-tetrahydro-2H-pyran-2-yloxy]-8-methyl-2-oxo-2H-chromen-3-yl}acetamide was developed as a novel, novobiocin-based, C-terminal inhibitor of Hsp90 whose ability to increase Hsp70 expression is linked to the presence of an acetamide substitution of the prenylated benzamide moiety of novobiocin. KU-32 protected against glucose-induced death of embryonic DRG (dorsal root ganglia neurons cultured for 3 days in vitro. Similarly, KU-32 significantly decreased neuregulin 1-induced degeneration of myelinated Schwann cell DRG neuron co-cultures prepared from WT (wild-type mice. This protection was lost if the co-cultures were prepared from Hsp70.1 and Hsp70.3 KO (knockout mice. KU-32 is readily bioavailable and was administered once a week for 6 weeks at a dose of 20 mg/kg to WT and Hsp70 KO mice that had been rendered diabetic with streptozotocin for 12 weeks. After 12 weeks of diabetes, both WT and Hsp70 KO mice developed deficits in NCV (nerve conduction velocity and a sensory hypoalgesia. Although KU-32 did not improve glucose levels, HbA1c (glycated haemoglobin or insulin levels, it reversed the NCV and sensory deficits in WT but not Hsp70 KO mice. These studies provide the first evidence that targeting molecular chaperones reverses the sensory hypoalgesia associated with DPN.

  11. Enhancement of radiation effect using beta-lapachone and underlying mechanism

    International Nuclear Information System (INIS)

    Ahn, Ki Jung; Lee, Hyung Sik; Bai, Se Kyung; Song, Chang Won

    2013-01-01

    Beta-lapachone (β-Lap; 3,4-dihydro-2, 2-dimethyl-2H-naphthol[1, 2-b]pyran-5,6-dione) is a novel anti-cancer drug under phase I/II clinical trials. (β-Lap has been demonstrated to cause apoptotic and necrotic death in a variety of human cancer cells in vitro and in vivo. The mechanisms underlying the (β-Lap toxicity against cancer cells has been controversial. The most recent view is that (β-Lap, which is a quinone compound, undergoes two-electron reduction to hydroquinone form utilizing NAD(P)H or NADH as electron source. This two-electron reduction of (β-Lap is mediated by NAD(P)H:quinone oxidoreductase (NQO1), which is known to mediate the reduction of many quinone compounds. The hydroquinone forms of (β-Lap then spontaneously oxidizes back to the original oxidized (β-Lap, creating futile cycling between the oxidized and reduced forms of (β-Lap. It is proposed that the futile recycling between oxidized and reduced forms of (β-Lap leads to two distinct cell death pathways. First one is that the two-electron reduced (β-Lap is converted first to one-electron reduced (β-Lap, i.e., semiquinone (β-Lap (SQ)- causing production of reactive oxygen species (ROS), which then causes apoptotic cell death. The second mechanism is that severe depletion of NAD(P)H and NADH as a result of futile cycling between the quinone and hydroquinone forms of β- p causes severe disturbance in cellular metabolism leading to apoptosis and necrosis. The relative importance of the aforementioned two mechanisms, i.e., generation of ROS or depletion of NAD(P)H/NADH, may vary depending on cell type and environment. Importantly, the NQO1 level in cancer cells has been found to be higher than that in normal cells indicating that β-Lap may be preferentially toxic to cancer cells relative to non-cancer cells. The cellular level of NQO1 has been found to be significantly increased by divergent physical and chemical stresses including ionizing radiation. Recent reports clearly demonstrated

  12. Biodistribution and radiation dosimetry of 18F-CP-18, a potential apoptosis imaging agent, as determined from PET/CT scans in healthy volunteers.

    Science.gov (United States)

    Doss, Mohan; Kolb, Hartmuth C; Walsh, Joseph C; Mocharla, Vani; Fan, Hong; Chaudhary, Ashok; Zhu, Zhihong; Alpaugh, R Katherine; Lango, Miriam N; Yu, Jian Q

    2013-12-01

    (18)F-CP-18, or (18S,21S,24S,27S,30S)-27-(2-carboxyethyl)-21-(carboxymethyl)-30-((2S,3R,4R,5R,6S)-6-((2-(4-(3-F18-fluoropropyl)-1H-1,2,3-triazol-1-yl)acetamido)methyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxamido)-24-isopropyl-18-methyl-17,20,23,26,29-pentaoxo-4,7,10,13-tetraoxa-16,19,22,25,28-pentaazadotriacontane-1,32-dioic acid, is being evaluated as a tissue apoptosis marker for PET imaging. The purpose of this study was to determine the biodistribution and estimate the normal-organ radiation-absorbed doses and effective dose from (18)F-CP-18. Successive whole-body PET/CT scans were obtained at approximately 7, 45, 90, 130, and 170 min after intravenous injection of (18)F-CP-18 in 7 healthy human volunteers. Blood samples and urine were collected between the PET/CT scans, and the biostability of (18)F-CP-18 was assessed using high-performance liquid chromatography. The PET scans were analyzed to determine the radiotracer uptake in different organs. OLINDA/EXM software was used to calculate human radiation doses based on the biodistribution of the tracer. (18)F-CP-18 was 54% intact in human blood at 135 min after injection. The tracer cleared rapidly from the blood pool with a half-life of approximately 30 min. Relatively high (18)F-CP-18 uptake was observed in the kidneys and bladder, with diffuse uptake in the liver and heart. The mean standardized uptake values (SUVs) in the bladder, kidneys, heart, and liver at around 50 min after injection were approximately 65, 6, 1.5, and 1.5, respectively. The calculated effective dose was 38 ± 4 μSv/MBq, with the urinary bladder wall having the highest absorbed dose at 536 ± 61 μGy/MBq using a 4.8-h bladder-voiding interval for the male phantom. For a 1-h voiding interval, these doses were reduced to 15 ± 2 μSv/MBq and 142 ± 15 μGy/MBq, respectively. For a typical injected activity of 555 MBq, the effective dose would be 21.1 ± 2.2 mSv for the 4.8-h interval, reduced to 8.3 ± 1.1 mSv for the 1-h interval

  13. White organic light-emitting devices based on blue fluorescent dye combined with dual sub-monolayer

    Energy Technology Data Exchange (ETDEWEB)

    Yang, Huishan, E-mail: yanghuishan1697@163.com

    2013-10-15

    White organic light-emitting devices have been realized by using highly blue fluorescent dye 4,4′-Bis(2,2-diphenyl-ethen-1-yl)-4,4′-di-(tert-butyl)phenyl(p-TDPVBi) and [2-methyl-6-[2-(2, 3,6,7-tetrahydro-1H, red fluorescent dye 5H-benzo[ij] quinolizin-9-yl) ethenyl]-4H-pyran-4-ylidene] propane-dinitrile(DCM2), together with well known green fluorescent dye quinacridone (QAD). The fabrication of multilayer WOLEDs did not involve the hard-to-control doping process. The structure of the device is ITO/m-MTDATA (45 nm)/NPB(8 nm)/p-TDPVBi(15 nm)/DCM2(x nm)/Alq{sub 3} (5 nm)/QAD(y nm)/Alq{sub 3}(55 nm)/LiF(1 nm)/Al, where 4,4′,4′′-tris{N,-(3-methylphenyl)-N-phenylamine}triphenylamine (m-MTDATA) acts as a hole injection layer, N,N′-bis-(1-naphthyl)-N, N′-diphenyl-1, 1′-biph-enyl-4, 4′-diamine (NPB) acts as a hole transport layer, p-TDPVBi acts as a blue emitting layer, DCM2 acts as a red emitting layer, QAD acts as a green emitting layer, tris-(8-hydroxyquinoline) aluminum (Alq{sub 3}) acts as an electron transport layer, and WOLEDs of devices A, B, C and D are different in layer thickness of DCM2 and QAD, respectively. To change the thickness of dual sub-monolayer DCM2 and QAD, the WOLEDs were obtained. When x, y=0.05, 0.1, the Commission Internationale de 1’Eclairage (CIE) coordinates of the device change from (0.4458, 0.4589) at 3 V to (0.3137, 0.3455) at 12 V that are well in the white region, and the color temperature and color rendering index were 5348 K and 85 at 8 V, respectively. Its maximum luminance was 35260 cd/m{sup 2} at 12 V, and maximum current efficiency and maximum power efficiency were 13.54 cd/A at 12 V and 6.68 lm/W at 5 V, respectively. Moreover, the current efficiency is largely insensitive to the applied voltage. The electroluminescence intensity of white EL devices varied only little at deferent dual sub-monolayer. Device D exhibited relatively high color rendering index (CRI) in the range of 88–90, which was essentially

  14. Patulin: incidence and control in apple products / Patulina: incidência e controle em derivados de maçã

    Directory of Open Access Journals (Sweden)

    Crispin Humberto Garcia-Cruz

    2009-07-01

    Full Text Available The patulin, (4hydroxy-4furo[3,2-c]pyran(6H-1,, is a thermal resistent mycotoxin produced by several species of fungi are common in plants, mainly in derivatives and apples. Studies on the toxicity in animals have shown that mycotoxin has character teratogenic, and carcinogenic in mice immunotoxic. Its biosynthesis is well understood involving a series of reactions of condensation and oxiredução, many catalyzed by enzymes. The danger of contamination of food with patulin, warning about the need for a more rigorous control. Recent research aimed their removal and degradation as well as increase the sensitivity of the tests, making them faster and at less cost. The removal of patulin of food is made with composite adsorbents, with inconvenience to diminish the quality of the product by adsorbs other components desirable. The degradation is made with sulfur compounds, which are not allowed in food in many countries, and the growth of yeasts, such as the production of cider. Many yeasts have resistance against patulin and produce compounds capable degrade it. Here, we reviewed research on patulin with emphasis on its influence in food industry, incidence of patulin in apple juice and other foods, maximum permissible concentrations, health effects, biosynthesis, removal, degradation and most widely used methods for its detection and quantification.A patulina, 4hidroxi-4furo[3,2-c] pirano(6H-1, micotoxina termo-resistente, é produzida por várias espécies de fungos, comuns em vegetais, produtos derivados e principalmente em maçãs. Estudos sobre a toxicidade em animais demonstraram esta micotoxina possui caráter teratogênico, cancerígeno e imunotóxico em camundongos. Sua biossíntese é bem compreendida envolvendo uma série de reações de condensação e de oxiredução, muitas catalisadas por enzimas. O perigo da contaminação de alimentos com patulina, alerta sobre a necessidade de um controle mais rigoroso. Pesquisas recentes objetivam

  15. Detection of fluorescent organic nanoparticles by confocal laser endomicroscopy in a rat model of Barrett’s esophageal adenocarcinoma

    Directory of Open Access Journals (Sweden)

    Dassie E

    2015-10-01

    Full Text Available Elisa Dassie,1,2,* Diletta Arcidiacono,2,3,* Iga Wasiak,4 Nunzio Damiano,5 Luigi Dall’Olmo,6 Cinzia Giacometti,7 Sonia Facchin,3 Mauro Cassaro,7 Ennio Guido,8 Franca De Lazzari,8 Oriano Marin,9,10 Tomasz Ciach,4 Suzanne Fery-Forgues,11,12 Alfredo Alberti,1,2 Giorgio Battaglia,13 Stefano Realdon13 1Department of Molecular Medicine, University of Padua, 2Venetian Institute of Molecular Medicine, 3Department of Surgery, Oncology and Gastroenterology, University of Padua, Padua, Italy; 4Faculty of Chemical and Process Engineering, Warsaw University of Technology, Warsaw, Poland; 5Department of Biomedical Sciences, University of Padua, Padua, 6Department of Emergency Medicine, “Santi Giovanni e Paolo” Hospital, Venice, 7Anatomic Pathology Unit, ULSS 15, Alta Padovana, Camposampiero, 8Gastroenterology Unit, Sant’Antonio Hospital, 9Interdepartmental Research Centre for Innovative Biotechnologies (CRIBI, University of Padua, 10Proteomics Facility, Azienda Ospedaliera di Padova, Padua, 11CNRS, ITAV-USR 3505, Toulouse, France; 12Université de Toulouse, ITAV-USR 3505, Toulouse, France; 13Endoscopy Unit, Veneto Institute of Oncology (IOV-IRCCS, Padua, Italy *These authors contributed equally to this work Abstract: For many years, novel strategies for cancer detection and treatment using nanoparticles (NPs have been developed. Esophageal adenocarcinoma is the sixth leading cause of cancer-related deaths in Western countries, and despite recent advances in early detection and treatment, its prognosis is still very poor. This study investigated the use of fluorescent organic NPs as potential diagnostic tool in an experimental in vivo model of Barrett’s esophageal adenocarcinoma. NPs were made of modified polysaccharides loaded with [4-(dicyanomethylene-2-methyl-6-(4-dimethylaminostyryl-4H-pyran] (DCM, a well-known fluorescent dye. The NP periphery might or might not be decorated with ASYNYDA peptide that has an affinity for esophageal cancer cells

  16. Radiotracers For Lipid Signaling Pathways In Biological Systems

    Energy Technology Data Exchange (ETDEWEB)

    Gatley, S. J. [Northeastern Univ., Boston, MA (United States)

    2016-09-26

    Bioorganic and Medicinal Chemistry Letters.Acylethanolamines. The work initially focused on myristoylethanolamine (MEA) labeled in the acyl moiety with tritium and with carbon-14. Standard coupling conditions were used and gave the desired radiotracers in decent yields. Tritiated product was needed for the search for binding sites of this signaling messenger, and C-14 labeled product for imaging using phosphorimaging screens. Additionally, C-14 MEA was prepared labeled in the ethanolamine moiety. Fluorine-18 labeled acylethanolamines. A multi-step synthesis was performed to obtain unlabeled N-(16- fluorohexadecanoyl)ethanolamide for an HPLC standard via the precursor 16-bromo-N- [2[(tetrahydro-2Hpyran-2-yl)oxy]ethyl]hexadecanoylamide. Near-anhydrous F-18 and the bromo precursor (approximately 2-3 mg) in acetonitrile (0.5 ml) were heated with a PETWave microwave reactor for 10 min at 80 °C. F-18 incorporation was checked using silica-gel TLC (8:92 methanol/chloroform). Deprotection was carried out using TFA. The crude product was purified by semi-preparative ODS HPLC (80:20 AcN/ H2O). The product peak was diluted in water, concentrated on an SPE column, and eluted in 1 mL EtOH. F-18 incorporation to form the THP protected product was >90% with negligible side products observed. Deprotection and HPLC purification proceeded successfully with >99% radiochemical l purity. Brain distribution studies were done in mice. This work was presented at the Society of Nuclear Medicine meeting in June 2012. Subsequent more detailed studies including whole body tissue distribution studies, microPET experiments and radiochromatographic studies were published in ACS Chemical Neurosciences in 2014. Iodine-125 labeled acylethanolamines. The precursor 12-bromo-N-[2[(tetrahydro-2H-pyran-2-yl)oxy]ethyl]dodecanoylamide was prepared and a 1 mg sample was subject to exchange labeling withradioiodide in refluxing acetonitrile for 1 hour. HPLC analysis as above indicated incorporation of about10% of