1990-24-5Relevant academic research and scientific papers
Structural, magnetic, and electronic properties of phenolic oxime complexes of Cu and Ni
Whyte, Alexander M.,Roach, Benjamin,Henderson, David K.,Tasker, Peter A.,Matsushita, Michio M.,Awaga, Kunio,White, Fraser J.,Richardson, Patricia,Robertson, Neil
experimental part, p. 12867 - 12876 (2012/03/07)
Square planar complexes of the type Ni(L1)2, Ni(L2)2, Cu(L1)2, and Cu(L 2)2, where L1H = 2-hydroxy-5-t- octylacetophenone oxime and L2H = 2-hydroxy-5-n-propylacetophenone oxime, have been prepared and characterized by single-crystal X-ray diffraction, cyclic voltammetry, UV/vis spectroscopy, field-effect-transistor measurements, density functional theory (DFT) and time-dependent DFT (TDDFT) calculations, and, in the case of the paramagnetic species, electron paramagnetic resonance (EPR) and magnetic susceptibility. Variation of alkyl groups on the ligand from t-octyl to n-propyl enabled electronic isolation of the complexes in the crystal structures of M(L1)2 contrasting with π-stacking interactions for M(L2)2 (M = Ni, Cu). This was evidenced by a one-dimensional antiferromagnetic chain for Cu(L2)2 but ideal paramagnetic behavior for Cu(L1)2 down to 1.8 K. Despite isostructural single crystal structures for M(L2) 2, thin-film X-ray diffraction and scanning electron microscopy (SEM) revealed different morphologies depending on the metal and the deposition method (vapor or solution). The Cu complexes displayed limited electronic interaction between the central metal and the delocalized ligands, with more mixing in the case of Ni(II), as shown by electrochemistry and UV/vis spectroscopy. The complexes M(L2)2 showed poor charge transport in a field-effect transistor (FET) device despite the ability to form π-stacking structures, and this provides design insights for metal complexes to be used in conductive thin-film devices.
Synthesis and evaluation of [2-(4-quinolyloxy)phenyl]methanone derivatives: Novel selective inhibitors of transforming growth factor-β kinase
Shimizu, Toshiyuki,Kimura, Kaname,Sakai, Teruyuki,Kawakami, Kazuki,Miyazaki, Tetsuko,Nakouji, Masayoshi,Ogawa, Akira,Ohuchi, Hitomi,Shimizu, Kiyoshi
supporting information; experimental part, p. 3326 - 3329 (2009/04/06)
We synthesized and evaluated various [2-(4-quinolyloxy)phenyl]methanone derivatives. These compounds had novel chemical structures that were distinct from those of previously reported inhibitors. Biological data suggested that these compounds inhibited transforming growth factor-β signaling by interacting with the ATP-binding pocket of the transforming growth factor-β type I receptor kinase domain. Here, we report on the synthesis and structure-activity relationships of the compounds in this series.
Regioselective synthesis of 5-alkylsalicylates, 5-alkyl-2-hydroxy- acetophenones, and 5-alkyl-2-hydroxy-benzophenones by [3 + 3] cyclization of 1,3-bis(silyl enol ethers) with 2-alkyl-1,1,3,3-tetraethoxypropanes
Mamat, Constantin,Buettner, Stefan,Trabhardt, Tiana,Fischer, Christine,Langer, Peter
, p. 6273 - 6275 (2008/02/10)
(Chemical Equation Presented) A variety of 5-alkylsalicylates, 5-alkyl-2-hydroxy-acetophenones, and 5-alkyl-2-hydroxy-benzophenones was regioselectively prepared by TiCl4 mediated formal [3 + 3] cyclization of 1,3-bis(silyl enol ethers) with 2-alkyl-1,1,3,3- tetraethoxypropanes.
Refinement and evaluation of a pharmacophore model for flavone derivatives binding to the benzodiazepine site of the GABAA receptor
Kahnberg, Pia,Lager, Erik,Rosenberg, Celia,Schougaard, Jette,Camet, Linda,Sterner, Olov,Nielsen, Elsebet ?stergaard,Nielsen, Mogens,Liljefors, Tommy
, p. 4188 - 4201 (2007/10/03)
To further develop and evaluate a pharmacophore model previously proposed by Cook and co-workers (Drug Des. Discovery 1995, 12, 193-248) for ligands binding to the benzodiazepine site of the GABAA receptor, 40 new flavone derivatives have been synthesized and their affinities for the benzodiazepine site have been determined. Two new regions of steric repulsive interactions between ligand and receptor have been characterized, and the receptor region in the vicinity of 6- and 3′-substituents has been mapped out. 2′-Hydroxy substitution is shown to give a significant increase in affinity, which is interpreted in terms of a novel hydrogen bond interaction with the previously proposed hydrogen bond-accepting site A2. On the basis of the results of these studies and the refined pharmacophore model, 5′-bromo-2′-hydroxy-6-methylflavone, the highest affinity flavone derivative reported so far (Ki = 0.9 nM), was successfully designed. A comparison of the pharmacophore model with a recently proposed alternative model (Marder; et al. Bioorg. Med. Chem., 2001, 9, 323-335) has been made.
Process for synthesis of 5-alkylbenzodioxoles
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, (2008/06/13)
The following description refers to a new process for the synthesis of 5-alkylated benzo[1,3]dioxole, comprising the following steps in sequence: catalytic hydrogenation of 4-acylphenol; acylation; displacement catalysed by Lewis acids; treatment with an inorganic basic compound and hydrogen peroxide; reaction with alkyl dihalides or dialkoxyalkanes. The process described herein, which yields 5-alkylbenzo[1,3]dioxoles, is economic and can be easily scaled up to industrial size.
Process for the synthesis of 5-allybenzodioxoles
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, (2008/06/13)
The following description refers to a new process for the synthesis of 5-alkylated benzo[1,3]dioxole, consisting in the following steps in sequence: catalytic hydrogenation of 4-acylphenol; acylation; displacement catalysed by Lewis acids; treatment with an inorganic basic compound and hydrogen peroxide; reaction with alkyl dihalides or dialkoxyalkanes. The process described herein, which yields 5-alkylbenzo[1,3]dioxoles, is economic and can be easily scaled up to industrial size.
Natural Benzofuranes. Synthesis of Eupomatenoids-1, -3, -4, -5, -6, -7, and -13
McKittrick, Brian A.,Stevenson, Robert
, p. 475 - 482 (2007/10/02)
A group of eupomatenoids, natural lignans possessing 2-aryl-3-methyl-5-propenylbenzofuran structures have been synthesized by short pathways which include the intramolecular Wittig reaction of an o-bromoethylaryl benzoate ester as a key step.
