- Synthesis and characterization of tris-(5-amino-8-hydroxyquinoline)aluminum complexes and their use as anode buffer layers in inverted organic solar cells
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Tris-(8-hydroxyquinoline)aluminum (Alq3) and its derivatives have been studied as light-emitting materials in organic light emitting diodes (OLEDs) and recently also as buffer layer materials in inverted organic solar cells based on the well-kn
- Manninen, Venla M.,Omar, Walaa A.E.,Heiskanen, Juha P.,Lemmetyinen, Helge J.,Hormi, Osmo E.O.
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- Synthesis of bis-8-hydroxyquinolines via an imination or a Suzuki-Miyaura coupling approach
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Bis-8-hydroxyquinolines represent an important yet underexplored class of potential ligands for the preparation of various coordination polymers, which can be used in a plethora of applications. In this work, the synthesis of two types of bis-8-hydroxyqui
- De Vreese, Rob,Muylaert, Koen,Maton, Cedric,Dereu, Lise,Taillieu, Frederique,Harth, Thomas,Van Deun, Rik,Vrielinck, Henk,Stevens, Christian V.,D'hooghe, Matthias
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- COMPOUNDS FOR THE INHIBITION OF UNREGULATED CELL GROWTH
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The present invention discloses compounds for inhibition of uncontrolled cell proliferation particularly cancer stem cells. Particularly, the invention relates to compounds of Formula I to XXII for the treatment of cancer.
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Page/Page column 54
(2020/07/14)
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- ANTICANCER COMPOUNDS
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The present invention discloses compounds for inhibition of uncontrolled cell proliferation particularly in cancer stem cells. Particularly, the invention relates to compounds of Formula III to XIV for the treatment of cancer, such as breast and prostate cancer.
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Page/Page column 64; 65; 66
(2018/11/22)
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- Optimization of 8-Hydroxyquinolines as Inhibitors of Catechol O-Methyltransferase
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A series of 8-hydroxy quinolines were identified as potent inhibitors of catechol O-methyltransferase (COMT) with selectivity for the membrane-bound form of the enzyme. Small substituents at the 7-position of the quinoline were found to increase metabolic stability without sacrificing potency. Compounds with good pharmacokinetics and brain penetration were identified and demonstrated in vivo modulation of dopamine metabolites in the brain. An X-ray cocrystal structure of compound 21 in the S-COMT active site shows chelation of the active site magnesium similar to catechol-based inhibitors. These compounds should prove useful for treatment of many neurological and psychiatric conditions associated with compromised cortical dopamine signaling.
- Buchler, Ingrid,Akuma, Daniel,Au, Vinh,Carr, Gregory,De León, Pablo,Depasquale, Michael,Ernst, Glen,Huang, Yifang,Kimos, Martha,Kolobova, Anna,Poslusney, Michael,Wei, Huijun,Swinnen, Dominique,Montel, Florian,Moureau, Florence,Jigorel, Emilie,Schulze, Monika-Sarah E. D.,Wood, Martyn,Barrow, James C.
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p. 9647 - 9665
(2018/11/23)
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- Hydroxy-Substituted Heteroarylpiperazines: Novel Scaffolds for β-Arrestin-Biased D2R Agonists
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By means of a formal structural hybridization of the antipsychotic drug aripiprazole and the heterocyclic catecholamine surrogates present in the β2-adrenoceptor agonists procaterol and BI-167107 (4), we designed and synthesized a collection of novel hydroxy-substituted heteroarylpiperazines and heteroarylhomopiperazines with high dopamine D2 receptor (D2R) affinity. In contrast to the weak agonistic behavior of aripiprazole, these ligands are capable of effectively mimicking those interactions of dopamine and the D2R that are crucial for an active state, leading to the recruitment of β-arrestin-2. Interestingly, some ligands show considerably lower intrinsic activity in guanine nucleotide exchange experiments at D2R and consequently represent biased agonists favoring β-arrestin-2 recruitment over canonical G protein activation. The ligands' agonistic properties are substantially driven by the presence of an endocyclic H-bond donor.
- M?nnel, Barbara,Dengler, Daniela,Shonberg, Jeremy,Hübner, Harald,M?ller, Dorothee,Gmeiner, Peter
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supporting information
p. 4693 - 4713
(2017/06/13)
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- Synthesis of Novel 5-(N-Substituted-Anilino)-8-Hydroxyquinolines via Hartwig-Buchwald Amination Reaction
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Three novel 5-(N-substituted-anilino)-8-benzyloxyquinoline derivatives were efficiently synthesized via Hartwig-Buchwald amination reaction. The new 5-(N-substituted-anilino)-8-benzyloxyquinolines were reduced for 1-3 h to give the corresponding 5-(N-substituted-anilino)-8-hydroxyquinolines. Extending the reduction reaction time to 7 h afforded the corresponding 1,2,3,4-tetrahydro-8-hydroxyquinoline derivatives.
- Omar, Walaa A. E.,Hormi, Osmo E. O.
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supporting information
p. 1937 - 1943
(2015/12/30)
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- Synthesis, characterization and DFT investigation of aluminum complexes of aryl-substituted-8-hydroxyquinoline
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New aryl substituted 8-hydroxyquinoline derivatives have been synthesized. The compounds were characterized by 1H, 13C-NMR spectroscopy and mass spectrometry. The aluminum complexes of these derivatives show strong green emission in the range 530-535 nm with high quantum yield compared to the parent tris (8-hydroxyquinolinato)aluminum(III) complex. The structure of the aryl-substituted 8-hydroxyquinoline aluminum complexes in the ground state have been optimized at the B3LYP/6-31G (*) level of theory. The parent 8-hydroxyquinoline has also been examined using this method with the same basis set. A clear correlation between the shortening of the Al-N bond and red shift in the fluorescence emission band was observed. We have also found that substitution at the 5 and 7 position of the 8-hydroxyquinoline ligand cause simultaneous energy lowering of both highest occupied molecular orbital and the lowest unoccupied molecular orbital with the 5, 7-aryl substituted derivatives exhibiting the greatest effect.
- Suliman, Fakhreldin O.,Al-Busafi, Saleh N.,Al-Risi, Moza,Al-Badi, Khalifa N.
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scheme or table
p. 1153 - 1159
(2012/03/27)
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- Effective manipulation of the electronic effects and its influence on the emission of 5-substituted tris(8-quinolinolate) aluminum(III) complexes
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The unique electron-transport and emissive properties of tris(8-quinolinolate) aluminum(III) (Alq3) have resulted in extensive use of this material for small molecular organic light-emitting diode (OLED) fabrication. So far, efforts to prepare stable and easy-to-process red/green/blue (RGB)-emitting Alq3 derivatives have met with only a limited success. In this paper, we describe how the electronic nature of various substituents, projected via an arylethynyl or aryl spacer to the position of the highest HOMO density (C5), may be used for effective emission tuning to obtain blue-, green-, and red-emitting materials. The synthetic strategy consists of four different pathways for the attachment of electron-donating and electron-withdrawing aryl or arylethynyl substituents to the 5-position of the quinolinolate ring. Successful tuning of the emission color covering the whole visible spectrum (λ = 450-800 nm) was achieved. In addition, the photophysical properties of the luminophores were found to correlate with the Hammett constant of the respective substituents, providing a powerful strategy with which to predict the optical properties of new materials. We also demonstrate that the electronic nature of the substituent affects the emission properties of the resulting complex through effective modification of the HOMO levels of the quinolinolate ligand.
- Montes, Victor A.,Pohl, Radek,Shinar, Joseph,Anzenbacher Jr., Pavel
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p. 4523 - 4535
(2008/02/07)
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- Red-Green-Blue Emission from Tris(5-aryl-8-quinolinolate)Al(III) Complexes
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A simple yet effective strategy for synthesis of 5-aryl-8-quinolinolate-based electroluminophores with tunable emission wavelengths is presented. Two different pathways for the attachment of electron-donating or electron-withdrawing aryl groups to the 5-p
- Pohl, Radek,Montes, Victor A.,Shinar, Joseph,Anzenbacher Jr., Pavel
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p. 1723 - 1725
(2007/10/03)
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