- Sustainable organophosphorus-catalysed Staudinger reduction
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A highly efficient and sustainable catalytic Staudinger reduction for the conversion of organic azides to amines in excellent yields has been developed. The reaction displays excellent functional group tolerance to functionalities that are otherwise prone to reduction, such as sulfones, esters, amides, ketones, nitriles, alkenes, and benzyl ethers. The green nature of the reaction is exemplified by the use of PMHS, CPME, and a lack of column chromatography.
- Lenstra, Danny C.,Lenting, Peter E.,Mecinovi?, Jasmin
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p. 4418 - 4422
(2018/10/17)
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- New Caffeic Acid Phenylethyl Ester Analogs Bearing Substituted Triazole: Synthesis and Structure-Activity Relationship Study towards 5-Lipoxygenase Inhibition
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Leukotrienes are biosynthesized by the conversion of arachidonic acid by 5-Lipoxygenase and play a key role in many inflammatory disorders. Inspired by caffeic acid phenylethyl ester (CAPE) (2) and an analog carrying a triazole substituted by cinnamoyl an
- Roy, Pierre-Philipe,Faye, Diene,Blanchard, Sébastien,Cormier, Marc,Doiron, Jérémie A.,Surette, Marc E.,Touaibia, Mohamed
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- Copper complexes bearing an NHC-calixarene unit: Synthesis and application in click chemistry
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The synthesis of N-heterocyclic carbene (NHC) copper complexes supported by calix[4]arene is reported. Mono-substituted calix[4]arene was prepared through conventional procedures, followed by the attachment of an imidazolyl group to create the precursor o
- Ourri, Benjamin,Tillement, Olivier,Tu, Tao,Jeanneau, Erwann,Darbost, Ulrich,Bonnamour, Isabelle
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p. 9477 - 9485
(2016/11/11)
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- Using the same hydroxamic acid derivative and HDAC8 inhibitor (by machine translation)
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Disclosed are: a compound which is capable of inhibiting the function of HDAC8; and an HDAC8 inhibitor. Specifically disclosed is a hydroxamic acid derivative which is characterized by being composed of a compound represented by general formula (1) (wherein X represents an aromatic substituent or an optionally substituted 3-8 membered ring, and n represents an integer of 0-20), or a pharmaceutically acceptable salt, hydrate, solvate or prodrug thereof.
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Paragraph 0108; 0125
(2016/10/09)
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- Direct C-H amination of arenes with alkyl azides under rhodium catalysis
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New horizons in the utility of azides: The rhodium-catalyzed intermolecular direct C-H amination of arenes with alkyl azides provides a convenient route to N-alkyl anilines (see scheme; DG=directing group). Alkyl azides with a wide range of functional groups reacted readily with various substrates, including benzamides, aromatic ketones, and flavones. Copyright
- Shin, Kwangmin,Baek, Yunjung,Chang, Sukbok
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supporting information
p. 8031 - 8036
(2013/08/23)
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- Rapid discovery of highly potent and selective inhibitors of histone deacetylase 8 using click chemistry to generate candidate libraries
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To find HDAC8-selective inhibitors, we designed a library of HDAC inhibitor candidates, each containing a zinc-binding group that coordinates with the active-site zinc ion, linked via a triazole moiety to a capping structure that interacts with residues on the rim of the active site. These compounds were synthesized by using click chemistry. Screening identified HDAC8-selective inhibitors including C149 (IC50 = 0.070 μM), which was more potent than PCI-34058 (6) (IC50 = 0.31 μM), a known HDAC8 inhibitor. Molecular modeling suggested that the phenylthiomethyl group of C149 binds to a unique hydrophobic pocket of HDAC8, and the orientation of the phenylthiomethyl and hydroxamate moieties (fixed by the triazole moiety) is important for the potency and selectivity. The inhibitors caused selective acetylation of cohesin in cells and exerted growth-inhibitory effects on T-cell lymphoma and neuroblastoma cells (GI50 = 3-80 μM). These findings suggest that HDAC8-selective inhibitors have potential as anticancer agents.
- Suzuki, Takayoshi,Ota, Yosuke,Ri, Masaki,Bando, Masashige,Gotoh, Aogu,Itoh, Yukihiro,Tsumoto, Hiroki,Tatum, Prima R.,Mizukami, Tamio,Nakagawa, Hidehiko,Iida, Shinsuke,Ueda, Ryuzo,Shirahige, Katsuhiko,Miyata, Naoki
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p. 9562 - 9575
(2013/01/16)
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- Efficient one-pot synthesis of 1,2,3-triazoles from benzyl and alkyl halides
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An efficient one-pot method for the preparation of 1,2,3-triazoles by 1,3-dipolar cycloaddition of in situ generated azides and alkynes is presented. This facile method can be applied to benzyl or alkyl halides and pure products are isolated by simple filtration.
- Kacprzak, Karol
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p. 943 - 946
(2007/10/03)
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- Samarium(0) and 1,1′-dioctyl-4,4′-bipyridinium dibromide: A novel electron-transfer system for the chemoselective reduction of aromatic nitro groups
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A mild and efficient electron-transfer method was developed for the chemoselective reduction of aromatic nitro groups using samarium(0) metal in the presence of a catalytic amount of 1,1′-dioctyl-4,4′-bipyridinium dibromide. This method was found to give the product aromatic amine in 79-99% yield with selectivity over a number of other functional and protecting groups such as alkene, azide, benzyl ether, nitrile, amide, halide, p-toluenesulfonamide, t-Boc, tert-butyldiphenylsilyl ether, and aliphatic nitro groups. Our results also indicate that samarium(0) plays an important role in the reduction process and that 1,1′-dioctyl-4,4′-bipyridinium dibromide acts as an electron-transfer catalyst and is essential in the activation of samarium(0) metal. The major active reducing agent responsible for the reduction is believed to be the radical cation species formed from 1,1′-dioctyl-4,4′-bipyridinium dibromide.
- Yu,Liu,Hu
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p. 919 - 924
(2007/10/03)
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