3197-25-9Relevant articles and documents
Synthesis of calix[4]pyrrole-based acrylate and acrylamide monomers: Precursors for preparation of anion-selective polymer membranes
Zyryanov, Grigory V.,Kinstle, Thomas H.,Anzenbacher Jr., Pavel
, p. 1171 - 1174 (2008)
Octamethylcalix[4]pyrrole derivatives with hydroxy alkyl and amino alkyl side chains were prepared and converted into the corresponding acrylate and acrylamide derivatives, respectively. Georg Thieme Verlag Stuttgart.
Thienopyrimidinone Based Sirtuin-2 (SIRT2)-Selective Inhibitors Bind in the Ligand Induced Selectivity Pocket
Sundriyal, Sandeep,Moniot, Sébastien,Mahmud, Zimam,Yao, Shang,Di Fruscia, Paolo,Reynolds, Christopher R.,Dexter, David T.,Sternberg, Michael J. E.,Lam, Eric W.-F.,Steegborn, Clemens,Fuchter, Matthew J.
, p. 1928 - 1945 (2017)
Sirtuins (SIRTs) are NAD-dependent deacylases, known to be involved in a variety of pathophysiological processes and thus remain promising therapeutic targets for further validation. Previously, we reported a novel thienopyrimidinone SIRT2 inhibitor with good potency and excellent selectivity for SIRT2. Herein, we report an extensive SAR study of this chemical series and identify the key pharmacophoric elements and physiochemical properties that underpin the excellent activity observed. New analogues have been identified with submicromolar SIRT2 inhibtory activity and good to excellent SIRT2 subtype-selectivity. Importantly, we report a cocrystal structure of one of our compounds (29c) bound to SIRT2. This reveals our series to induce the formation of a previously reported selectivity pocket but to bind in an inverted fashion to what might be intuitively expected. We believe these findings will contribute significantly to an understanding of the mechanism of action of SIRT2 inhibitors and to the identification of refined, second generation inhibitors.
Gold N-Heterocyclic Carbene Catalysts for the Hydrofluorination of Alkynes Using Hydrofluoric Acid: Reaction Scope, Mechanistic Studies and the Tracking of Elusive Intermediates
Bédard, Sandrine,Cavallo, Luigi,Falivene, Laura,Gauthier, Rapha?l,Nolan, Steven P.,Paquin, Jean-Fran?ois,Saab, Marina,Tzouras, Nikolaos V.,Van Hecke, Kristof,Zhang, Ziyun
supporting information, (2021/12/09)
An efficient and chemoselective methodology deploying gold-N-heterocyclic carbene (NHC) complexes as catalysts in the hydrofluorination of terminal alkynes using aqueous HF has been developed. Mechanistic studies shed light on an in situ generated catalyst, formed by the reaction of Br?nsted basic gold pre-catalysts with HF in water, which exhibits the highest reactivity and chemoselectivity. The catalytic system has a wide alkyl substituted-substrate scope, and stoichiometric as well as catalytic reactions with tailor-designed gold pre-catalysts enable the identification of various gold species involved along the catalytic cycle. Computational studies aid in understanding the chemoselectivity observed through examination of key mechanistic steps for phosphine- and NHC-coordinated gold species bearing the triflate counterion and the elusive key complex bearing a bifluoride counterion.
5-phenoxy primaquine analogs and the tetraoxane hybrid as antimalarial agents
Jansongsaeng, Somruedee,Kamchonwongpaisan, Sumalee,Khotavivattana, Tanatorn,Pengon, Jutharat,Srimongkolpithak, Nitipol
, (2021/07/17)
The rapid emergence of drug resistance to the current antimalarial agents has led to the urgent need for the discovery of new and effective compounds. In this work, a series of 5-phenoxy primaquine analogs with 8-aminoquinoline core (7a–7h) was synthesize
Substituted imidazo[4,5-c]quinoline macrocyclic compound as multi-target kinase inhibitor
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Paragraph 0128-0131, (2020/04/17)
The invention discloses a substituted imidazo[4,5-c]quinoline macrocyclic compound as a multi-target kinase inhibitor, and relates to a compound represented by a formula (I) or a pharmaceutically acceptable salt, a solvate, a polymorphic substance or an isomer thereof, and applications of the compound in preparation of a medicine for treating ALK-mediated diseases.
Synthesis method of 2-methyl pyrroline
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Paragraph 0014; 0016-0017, (2020/06/16)
The invention discloses a synthesis method of 2-methyl pyrroline. The preparation method comprises the following steps: adding valeryl chloride and phthaloyl potassium salt into a high-boiling-point solvent and carrying out heating reflux for 5 to 15 hours; and S2, after the reaction liquid is cooled, filtering the reaction liquid, concentrating the reaction liquid, adding methanol for pulping toobtain a crude product, adding the crude product obtained in S1 into hydrochloric acid for heating reflux, after the reaction is completed, performing concentrating to dryness, adding water into residual liquid for dissolving, adjusting the pH value to be about 11 by using sodium carbonate, performing extracting for 3-5 times by using dichloromethane, and performing concentrating and drying, and distilling to obtain a product. According to the synthetic method of the 2-methyl pyrroline, disclosed by the invention, the used initial raw materials are easy to obtain, the preparation is convenient, the enlarged production is easy, the intermediate product is stable, and the collection efficiency is high.
The gold-catalyzed formal hydration, decarboxylation, and [4+2] cycloaddition of alkyne derivatives featuring L2/Z-type diphosphinoborane ligands
Matsumoto, Chiaki,Yamada, Masayuki,Dong, Xun,Mukai, Chisato,Inagaki, Fuyuhiko
supporting information, p. 1321 - 1323 (2018/10/15)
The catalytic formal hydration of alkynes and decarbox-ylation of alkynoic acid were developed using a Au catalyst featuring a Z-ligand. Furthermore, the intramolecular [4+2] cycloaddition of the alkynoic acid-alkene derivative for the formation of the oxabicyclo[4.4.0] skeleton also proceeded.
Palladium-catalysed anti-Markovnikov selective oxidative amination
Kohler, Daniel G.,Gockel, Samuel N.,Kennemur, Jennifer L.,Waller, Peter J.,Hull, Kami L.
, p. 333 - 340 (2018/02/27)
In recent years, the synthesis of amines and other nitrogen-containing motifs has been a major area of research in organic chemistry because they are widely represented in biologically active molecules. Current strategies rely on a multistep approach and require one reactant to be activated prior to the carbon-nitrogen bond formation. This leads to a reaction inefficiency and functional group intolerance. As such, a general approach to the synthesis of nitrogen-containing compounds from readily available and benign starting materials is highly desirable. Here we present a palladium-catalysed oxidative amination reaction in which the addition of the nitrogen occurs at the less-substituted carbon of a double bond, in what is known as anti-Markovnikov selectivity. Alkenes are shown to react with imides in the presence of a palladate catalyst to generate the terminal imide through trans-aminopalladation. Subsequently, olefin isomerization occurs to afford the thermodynamically favoured products. Both the scope of the transformation and mechanistic investigations are reported.
Tuning Regioselectivity of Wacker Oxidation in One Catalytic System: Small Change Makes Big Step
Hu, Kang-Fei,Ning, Xiao-Shan,Qu, Jian-Ping,Kang, Yan-Biao
, p. 11327 - 11332 (2018/09/06)
A regioselectivity switchable aerobic Wacker-Tsuji oxidation has been developed using catalytic tert-butyl nitrite as a simple organic redox cocatalyst. By solely switching the solvent, either substituted aldehydes or ketones could be prepared under mild
Oxidation of Secondary Methyl Ethers to Ketones
Gilissen, Pieter J.,Blanco-Ania, Daniel,Rutjes, Floris P. J. T.
, p. 6671 - 6679 (2017/07/15)
We present a mild way of converting secondary methyl ethers into ketones using calcium hypochlorite in aqueous acetonitrile with acetic acid as activator. The reaction is compatible with various oxygen- and nitrogen-containing functional groups and afforded the corresponding ketones in up to 98% yield. The use of this methodology could expand the application of the methyl group as a useful protecting group.
