- Synthesis of Nanostructured Organosilicon Luminophores Based on Phenyloxazoles
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A series of nanostructured organosilicon luminophores (NOLs) composed of a central 1,4-bis(5-phenyl-1,3-oxazol-2-yl)benzene (POPOP) acceptor chromophore and various peripheral p-terphenyl and 2,5-diphenyl-1,3-oxazole donor fragments have been synthesized for the first time using van Leusen reaction and direct palladium-catalyzed C-arylation of oxazole ring. Due to different functionalities of the silicon branching centers, NOLs with different donor-acceptor ratios have been obtained. The synthesized structures are expected to possess good optical characteristics for use in photonics and optoelectronics.
- Skorotetcky,Borshchev,Cherkaev,Ponomarenko
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- Tandem oxidative isocyanide-based cycloaddition reactions in the presence of MIL-101(Cr) as a reusable solid catalyst
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The tandem oxidative three-component synthesis of two types of the heterocycles such as furans and imidazopyridines, via isocyanides [1+4] cycloaddition reactions in the presence of MIL-101(Cr) under aerobic conditions are reported. When the 4-toluenesulfonylmethyl isocyanide was used, an unexpected [3+2] cycloaddition reaction of isocyanides with aldehydes accomplished and dihydrophenyloxazoles and phenyloxazoles produced. These syntheses were successfully carried out using a wide scope of the substrates.
- Shaabani, Ahmad,Sepahvand, Heshmatollah,Amini, Mostafa M.,Hashemzadeh, Alireza,Borjian Boroujeni, Mahmoud,Badali, Elham
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p. 1832 - 1837
(2018/03/07)
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- Targeted Polypharmacology: Discovery of a Highly Potent Non-Hydroxamate Dual Matrix Metalloproteinase (MMP)-10/-13 Inhibitor
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Matrix metalloproteinases (MMPs) play a key role in many diseases like cancer, atherosclerosis or arthritis. Interest in MMP inhibition has been revitalized very recently as the knowledge on the underlying network of biological pathways is steadily growing. On the basis of this new insight into the relevance of MMP-10 and MMP-13 within the MMP network and the ban of hydroxamate inhibitors from clinical development, the discovery of non-hydroxamate multitarget drugs against specific MMPs is of foremost interest. Here, we disclose the discovery of a very potent and selective non-hydroxamate MMP-10/-13 inhibitor. The high potency (IC50 of 31 nM [MMP-10] and 5 nM [MMP-13]) and selectivity over MMP-1, -2, -3, -7, -8, -9, -12, and -14 enable this compound to decipher disease causing MMP networks and to generate new treatment options through targeted polypharmacology.
- Senn, Nicole,Ott, Michael,Lanz, Jan,Riedl, Rainer
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p. 9585 - 9598
(2017/12/26)
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- Tandem cycloaddition-decarboxylation of α-keto acid and isocyanide under oxidant-free conditions towards monosubstituted oxazoles
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An efficient method, tandem [3 + 2] cycloaddition-decarboxylation of α-keto acid and isocyanide promoted by copper salt, has been developed. Under oxidant-free conditions, a series monosubstituted oxazoles have been constructed. Different from the traditional application of α-oxo acids as acyl surrogates, the elegant approach herein ingeniously avoids consuming excess oxidants.
- Zhang, Ling-Juan,Xu, Mei-Chen,Liu, Jie,Zhang, Xian-Ming
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p. 73450 - 73453
(2016/08/18)
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- A One-Pot Tandem Approach for the Synthesis of 5-(Het)aryloxazoles from Substituted (Het)aryl Methyl Alcohols and Benzyl Bromides
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A new modified van Leusen strategy has been developed for the synthesis of biologically significant 5-substituted oxazoles by the reaction of (het)aryl methyl alcohols or benzyl bromides as precursors with tosylmethylisocyanide (TosMIC) under basic conditions. This method is efficient, takes place under mild reaction conditions, and is tolerant of various functional groups with high yield.
- Vinay Kumar, Koravangala S.,Swaroop, Toreshettahally R.,Rajeev, Narasimhamurthy,Vinayaka, Ajjampura C.,Lingaraju, Gejjalagere S.,Rangappa, Kanchugarakoppal S.,Sadashiva, Maralinganadoddi P.
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supporting information
p. 1363 - 1366
(2016/06/01)
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- Synthesis and biological activity of 5-(4-methoxyphenyl)-oxazole derivatives
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5-(4′-Methoxyphenyl)-oxazole (MPO), originally reported as a synthetic compound, was isolated from fungal culture broth as an inhibitor of hatch and growth of Caenorhabditis elegans. Nineteen MPO derivatives were chemically synthesized, but showed no effect on C. elegans hatch and growth. These findings strongly suggested that the whole structure of MPO is essential for anti-C. elegans activity.
- Yamamuro, Daisuke,Uchida, Ryuji,Ohtawa, Masaki,Arima, Shiho,Futamura, Yushi,Katane, Masumi,Homma, Hiroshi,Nagamitsu, Tohru,Osada, Hiroyuki,Tomoda, Hiroshi
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supporting information
p. 313 - 316
(2015/04/13)
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- A robust and efficient catalyst possessing an electron-deficient ligand for the palladium-catalyzed direct arylation of heteroarenes
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The exploration of the direct arylation capacity of a unique, thermally stable, and air-stable Pd0-phosphine catalyst is reported. Besides decisively contributing to catalyst robustness, the electron-deficient trifluoromethyl-substituted triphenylphosphine ligands make the palladium center more electron-deficient and accelerate the direct arylation step. The combination of only 0.5-2 mol-% of the catalyst and a substoichiometric quantity of pivalic acid generates an efficient system to promote biaryl-forming reactions of a broad range of electronically varied hetarenes and aryl bromides. The observed regioselective arylations suggest that a concerted metalation-deprotonation pathway is involved in the C-H activation step.
- Jakab, Alexandra,Dalicsek, Zoltn,Sos, Tibor
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supporting information
p. 56 - 59
(2015/02/19)
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- Copper-mediated C-H/C-H biaryl coupling of benzoic acid derivatives and 1,3-azoles
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Hot couple: A precious-metal-free copper-mediated intermolecular direct biaryl coupling of benzoic acid derivatives and 1,3-azoles has been developed. The key to success is the installation of an amide-based bidentate coordinating group, which is easily removed and transformed into the parent ester groups after the coupling reaction. Kinetic studies indicate that the rate-limiting step is the aromatic C-H bond cleavage of benzoic acid derivatives. Copyright
- Nishino, Mayuko,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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supporting information
p. 4457 - 4461
(2013/05/22)
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- Copper-mediated dehydrogenative biaryl coupling of naphthylamines and 1,3-azoles
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A copper-mediated dehydrogenative biaryl cross-coupling of naphthylamines and 1,3-azoles has been developed. The key to its success is the introduction of N,N-bidentate coordination system based on the picolinamide directing group. The reaction proceeds s
- Odani, Riko,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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p. 11045 - 11052
(2013/11/19)
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- Mild palladium-catalyzed regioselective direct arylation of azoles promoted by tetrabutylammonium acetate
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A mild, general, and convenient palladium-catalyzed direct arylation of the 5-position of azoles with aryl bromides, efficiently promoted by tetrabutylammonium acetate, is described. 1-Methylpyrazole, oxazole, and thiazole reacted at 70°C in N,N-dimethyla
- Bellina, Fabio,Lessi, Marco,Manzini, Chiara
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p. 5621 - 5630
(2013/09/12)
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- Copper-mediated and copper-catalyzed cross-coupling of indoles and 1,3-azoles: Double C-H activation
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A new bronze age: The described copper-mediated cross-coupling with double C-H activation can provide a convergent access to indole-containing biheteroaryls that are of high interest in pharmaceutical and medicinal chemistry. In this strategy an easily attachable and detachable 2-pyrimidyl directing group is used. Moreover, a variant that is catalytic in copper is achieved by using atmospheric oxygen as an ideal co-oxidant (see scheme). Copyright
- Nishino, Mayuko,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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supporting information; experimental part
p. 6993 - 6997
(2012/10/07)
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- Copper-mediated intermolecular direct biaryl coupling
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Copper-mediated intermolecular direct biaryl coupling of arylazines and azoles via dual C-H bond cleavage proceeds even without palladium catalysts. The reaction system shows the high potential of copper salts in direct C-H arylation chemistry and provides a new approach to biaryl motifs, which are ubiquitous in pharmaceuticals and functional materials.
- Kitahara, Masanori,Umeda, Nobuyoshi,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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supporting information; body text
p. 2160 - 2162
(2011/04/23)
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- Nickel-catalyzed direct C-H arylation and alkenylation of heteroarenes with organosilicon reagents
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"Chemical Equation Presented" Breaking the Si-lence: The direct crosscoupling of heteroarenes with aryl- or alkenylsilanes proceeds efficiently, in the presence of a nickel catalyst, to create a wide range of aryl- and alkenyl-heteroaryl bonds efficiently (see scheme; DMAc= N.N-dimethylacetamide, bpy = 2,2′-bipyridine). This catalysis represents a new avenue for using organosilanes in the catalytic C-H functionalization chemistry.
- Hachiya, Hitoshi,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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supporting information; body text
p. 2202 - 2205
(2010/06/18)
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- CONVERSION OF TRIAZOLIDES INTO OXAZOLES BY FLASH-VACUUM PYROLYSIS.
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Flash-vacuum pyrolysis of azolides of 1,2,4-triazole affords 5-monosubstituted oxazoles.
- Maquestiau, A.,Puk, E.,Flammang, R.
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p. 4023 - 4024
(2007/10/02)
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