- Positional isomers of bispyridine benzene derivatives induce efficacy changes on mGlu5negative allosteric modulation
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Modulation of metabotropic glutamate receptor 5 (mGlu5) with partial allosteric antagonists has received increased interest due to their favourable in?vivo activity profiles compared to the unfavourable side-effects of full inverse agonists. He
- Gómez-Santacana, Xavier,Dalton, James A.R.,Rovira, Xavier,Pin, Jean Philippe,Goudet, Cyril,Gorostiza, Pau,Giraldo, Jesús,Llebaria, Amadeu
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p. 567 - 576
(2017/01/28)
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- Structure-Activity Relationships for Negative Allosteric mGluR5 Modulators
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A series of compounds based on the mGluR5-selective ligand 2-methyl-6-(phenylethynyl)pyridine (MPEP) were designed and synthesized. The compounds were found to be either structural analogues of MPEP, substituted monomers, or dimeric analogues. All compounds retained mGluR5 selectivity with only weak or no activity at other mGluRs or iGluRs. The substituted analogue, 1,3-bis(pyridin-2-ylethynyl)benzene (19), is a potent negative modulator at mGluR5, whereas all other compounds lost potency relative to MPEP and showed that activity is highly dependent on the position of the nitrogen atom in the pyridine moieties. A homology modeling and ligand docking study was used to understand the binding mode and the observed selectivity of compound 19.
- Kaae, Birgitte H.,Harpsoe, Kasper,Kvist, Trine,Mathiesen, Jesper M.,Molck, Christina,Gloriam, David,Jimenez, Hermogenes N.,Uberti, Michelle A.,Nielsen, Soren M.,Nielsen, Birgitte,Braeuner-Osborne, Hans,Sauerberg, Per,Clausen, Rasmus P.,Madsen, Ulf
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experimental part
p. 440 - 451
(2012/06/04)
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- Pd complexes with trans-chelating ligands composed of two pyridyl groups and rigid π-conjugated backbone
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1,2-Bis(2-pyridylethynyl)benzene derivatives, having two pyridyl groups and π-conjugated backbone, were prepared from the 1:2 Sonogashira reaction of 1,2-diiodobenzene with 2-alkynyl pyridines. The obtained ligands react with the palladium(II) complexes such as [PdCl2(cod)] and [PdCl 2(MeCN)2] to form the complexes with the ligands coordinated in a trans-chelating bidentate mode. The ligand obtained from 1,3-diiodobenzene and 2-alkynyl pyridine bridges two Pd(II) centers, yielding a dipalladium complex. A dichloropalladium complex with the trans-chelating ligand, containing two methoxy groups in the central arylene group, promotes coupling of phenyl lithium and of phenyl acetylene to yield the respective homo-coupling products. The ligand displacement reactions of {bis(2-pyridylethynyl)benzene}palladium(II) complex with phosphine and dinitrogen ligands, such as PPh3, dppe, dppb, en, tmeda, bpy and phen, takes place smoothly to release the trans-chelating ligand.
- Jung, Miso,Suzaki, Yuji,Saito, Takashi,Shimada, Kyoichi,Osakada, Kohtaro
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experimental part
p. 168 - 174
(2012/08/28)
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- Palladium-catalyzed copper-free sonogashira coupling reaction in water and acetone
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An efficient palladium-catalyzed copper-free Sonogashira reaction in water and acetone has been developed under mild conditions. The results showed that the aryl iodides could carry out the cross-coupling reaction with a variety of terminal alkynes in high yields in water-acetone in the absence of amine, copper(I) salts, or phosphine ligands at 60°C for one hour, and good yields were obtained for aryl bromides at 60°C for 12-24 hours in the presence of triphenylphosphine and piperidine. The method could be used to synthesize polyethynyl aromatic compounds in a one-pot reaction. Georg Thieme Verlag Stuttgart.
- Shi, Shengyin,Zhang, Yuhong
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p. 1843 - 1850
(2008/02/10)
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- Banana-shaped oligo(aryleneethynylene)s: Synthesis and light-emitting characteristics
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(Chemical Equation Presented) Pick of the bunch: Banana-shaped molecules 1 and 2 containing dimethoxybenzene and pyridine units are highly efficient emitters of violet light despite the interruption of the π conjugation because of meta substitution. The c
- Yamaguchi, Yoshihiro,Kobayashi, Shigeya,Wakamiya, Tateaki,Matsubara, Yoshio,Yoshida, Zen-Ichi
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p. 7040 - 7044
(2007/10/03)
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