- DMSO-Enabled Selective Radical O?H Activation of 1,3(4)-Diols
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Control of selectivity is one of the central topics in organic chemistry. Although unprecedented alkoxyl-radical-induced transformations have drawn a lot of attention, compared to selective C?H activation, selective radical O?H activation remains less explored. Herein, we report a novel selective radical O?H activation strategy of diols by combining spatial effects with proton-coupled electron transfer (PCET). It was found that DMSO is an essential reagent that enables the regioselective transformation of diols. Mechanistic studies indicated the existence of the alkoxyl radical and the selective interaction between DMSO and hydroxyl groups. Moreover, the distal C?C cleavage was realized by this selective alkoxyl-radical-initiation protocol.
- Han, Bing,Jiao, Ning,Jin, Rui,Liu, Guoquan,Liu, Jianzhong,Zhang, Ziyao,Zhu, Yuchao
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supporting information
p. 19851 - 19856
(2020/09/04)
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- Synthesis and evaluation of 1H-pyrrole-2,5-dione derivatives as cholesterol absorption inhibitors for suppressing the formation of foam cells and inflammatory response
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Excess lipid accumulation in the arterial intima and formation of macrophage-derived foam cells in the plaque could cause atherosclerotic lesion. Cholesterol absorption inhibitors could suppress the lipid accumulation of human macrophage, inflammatory res
- Yuan, Xinrui,Xia, Yineng,Lu, Peng,Zhu, Lijuan,Zhong, Yuejiao,Wang, Yubin
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p. 1435 - 1447
(2018/03/05)
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- 3,4-diaryl maleimide derivative and preparation method and application thereof
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The invention discloses a 3,4-diaryl maleimide derivative represented by a general formula I and a medicinal salt form thereof. The invention further discloses a preparation method of the mentioned 3,4-diaryl maleimide derivative and application of the 3,
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Paragraph 0088; 0089; 0090
(2017/08/23)
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- Identification of novel small-molecule inhibitors targeting menin-MLL interaction, repurposing the antidiarrheal loperamide
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Leukemia with a mixed lineage leukemia (MLL) rearrangement, which harbors a variety of MLL fusion proteins, has a poor prognosis despite the latest improved treatment options. Menin has been reported to be a required cofactor for the leukemogenic activity of MLL fusion proteins. Thus, the disruption of the protein-protein interactions between menin and MLL represents a very promising strategy for curing MLL leukemia. Making use of menin-MLL inhibitors with a shape-based scaffold hopping approach, we have discovered that the antidiarrheal loperamide displays previously unreported mild inhibition for the menin-MLL interaction (IC50 = 69 ± 3 μM). In an effort to repurpose this drug, a series of chemical modification analyses was performed, and three of the loperamide-based analogues, DC-YM21, DC-YM25 and DC-YM26 displayed better activities with IC50 values of 0.83 ± 0.13 μM, 0.69 ± 0.07 μM and 0.66 ± 0.05 μM, respectively. Further treatment with DC-YM21 demonstrated potent and selective blockage of proliferation and induction of both cell cycle arrest and differentiation of leukemia cells harboring MLL translocations, which confirmed the specific mechanism of action. In conclusion, molecules of a novel scaffold targeting menin-MLL interactions were reported and they may serve as new potential therapeutic agents for MLL leukemia.
- Yue, Liyan,Du, Juanjuan,Ye, Fei,Chen, Zhifeng,Li, Lianchun,Lian, Fulin,Zhang, Bidong,Zhang, Yuanyuan,Jiang, Hualiang,Chen, Kaixian,Li, Yuanchao,Zhou, Bing,Zhang, Naixia,Yang, Yaxi,Luo, Cheng
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supporting information
p. 8503 - 8519
(2016/09/28)
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- Synthesis of oxazolidin-2-ones and imidazolidin-2-ones directly from 1,3-diols or 3-amino alcohols using iodobenzene dichloride and sodium azide
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A general and efficient method for the synthesis of oxazolidin-2-ones and imidazolidin-2-ones directly from 1,3-diols and 3-amino alcohols has been developed using the same reagent combination of iodobenzene dichloride (PhICl2) and sodium azide (NaN3).
- He, Tian,Gao, Wen-Chao,Wang, Wei-Kun,Zhang, Chi
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supporting information
p. 1113 - 1118
(2014/04/03)
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- Double reformatsky reaction: Divergent synthesis of δ-hydroxy-β- ketoesters
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The double Reformatsky reaction, tandem addition of two molecules of zinc alkanoate to a carbonyl compound, and its synthetic application to a series of δ-hydroxy-β-ketoesters has been developed. The key to accelerate the double Reformatsky reaction is considered to be a complex-induced proximity effect of the in situ generated zinc alkoxide coordinated with the pyridyl group of the substrate or bidentate amines. A noteworthy feature of the reaction system is its high tolerance of functional groups due to the moderate nucleophilicity of organozinc reagents and the mild reaction conditions. Moreover, spectroscopic and crystallographic analyses of the zinc complex of the double Reformatsky product support the proposed mechanism of reaction site discrimination for ketones, aldehydes, nitriles, carboxylic acid anhydrides, and esters.
- Mineno, Masahiro,Sawai, Yasuhiro,Kanno, Kazuaki,Sawada, Naotaka,Mizufune, Hideya
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supporting information
p. 5843 - 5850
(2013/07/26)
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- 3,6-DISUBSTITUTED AZABICYCLO [3.1.0] HEXANE DERIVATIVES AS MUSCARINIC RECEPTOR ANTAGONISTS
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The present invention generally relates to muscarinic receptor antagonists, which are useful, among other uses, for the treatment of various diseases of the respiratory, urinary and gastrointestinal systems mediated through muscarinic receptors. The invention also relates to the process for the prepration of disclosed compounds, pharmaceutical compositions containing the disclosed compounds, and the methods for treating diseases mediated through muscarinic receptors.
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Page/Page column 21
(2008/06/13)
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- New application of bromotrimethylsilane: Elaboration of aldehydes/ketones into homologous α,β-unsaturated esters via β-hydroxy esters
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α,β-Unsaturated esters are formed when β-hydroxy esters react with bromotrimethylsilane which is generated from chlorotrimethylsilane- lithium bromide in acetonitrile. Copyright Taylor & Francis, Inc.
- Suri, Suresh C.,Marcischak, Jacob C.
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p. 379 - 387
(2007/10/03)
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- Reformatsky reaction of α-chloroesters with carbonyl compounds with commercially available zinc
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The condensation of α-chloroesters with aliphatic as well as aromatic ketones with commercially available zinc without any external metal additives is described.
- Chavan, Subhash P.,Shivasankar,Sivappa
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p. 406 - 407
(2007/10/03)
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- Synthesis of β-hydroxy esters using highly active manganese
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A modified Reformatsky reaction is reported using highly reactive manganese (Mn*). The active manganese was found to readily react with α-haloester in the presence of aldehydes and ketones to yield the corresponding β-hydroxy esters. The reaction is carried out at room temperature in the absence of Lewis acid or trapping agents.
- Suh, YoungSung,Rieke, Reuben D.
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p. 1807 - 1809
(2007/10/03)
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- Microwave-promoted synthesis of β-hydroxyesters by the Reformatsky reaction in the absence of solvent
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A microwave-promoted Reformatsky reaction of aldehydes and ketones with ethyl bromoacetate, in the absence of solvent, using activated zinc metal and solid NH4Cl afforded the corresponding β-hydroxyesters in good to excellent yields.
- Gholap, Atul R.,Chavan, Abhijit P.
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p. 374 - 376
(2007/10/03)
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- High-intensity ultrasound-promoted reformatsky reactions
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Reformatsky reactions of a phenyl ketone, an α-bromoester, zinc dust, and a catalytic amount of iodine in dioxane under high-intensity ultrasound (HIU) irradiation from an ultrasonic probe give high yields of β-hydroxyesters in short reaction times. A ser
- Ross, Nathan A.,Bartsch, Richard A.
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p. 360 - 366
(2007/10/03)
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- A novel synthesis of imidazoles via the cycloaddition of nitrile ylides to their imidoyl chloride precursors
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The synthesis of imidazoles via the cycloaddition of nitrile ylides to their imidoyl chloride precursors was presented. The nitrile ylides were prepared by the 1,3-dehydrochlorination of imidoyl chlorides. It was shown that the HOMO of the 'bent' nitrile ylide is heavily localized on the methane terminus and is compatible with protonation at this carbon in substituted nitrile ylides and with the regioisomers obtained in biomolecular nitrile ylide cycloadditions. The observed regiochemistry of the cycloaddition was rationalized by energy calculations on the frontier molecular orbitals of the reactants using semi-empirical methods.
- Groundwater, Paul W.,Garnett, Ian,Morton, Andrew J.,Sharif, Toqir,Coles, Simon J.,Hursthouse, Michael B.,Nyerges, Miklos,Anderson, Rosaleen J.,Bendell, David,McKillop, Alexander,Zhang, Weimin
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p. 2781 - 2787
(2007/10/03)
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- Electrochemical activation of zinc in the coupling reaction of α-bromoesters with carbonyl compounds
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The Reformatsky reaction has been examined using a mild and effective method of electrochemical zinc activation, based on the cathodic reduction of a catalytic amount of zing bromide in acetonitrile.
- Rollin, Y.,Gebehenne, C.,Derien, S.,Dunach, E.,Perichon, J.
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- Metal Exchange between an Electrogenerated Organonickel Species and Zinc Halide: Application to an Electrochemical, Nickel-Catalyzed Reformatsky Reaction
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The mechanism of the electroreductive coupling of α-chloro esters or α-chloro nitriles with carbonyl compounds by the means of a sacrificial zinc anode and a nickel catalyst was elucidated by electroanalytical techniques.The mechanism involved reduction of a Ni(II) complex to a Ni(0) complex, oxidative addition of the α-chloro ester to the Ni(0) complex, and a Zn(II)/Ni(II) exchange, leading to an organozinc Reformatsky reagent.The electrosynthesis of various β-hydroxy esters, β-hydroxy nitriles, and 2,3-epoxy esters was successfully achieved under extremely mild conditions.
- Conan, Annie,Sibille, Soline,Perichon, Jacques
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p. 2018 - 2024
(2007/10/02)
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- Palladium catalyzed cyclocarbonylation of 3,3-diarylallyl acetates
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Palladium-catalyzed cyclocarbonylation of 3,3-diarylallyl acetates afforded 4-aryl-substituted 1-naphthyl acetates where the cyclization occurred selectively on the more electron-rich ring.
- Iwasaki, Masakazu,Ishii, Youichi,Hidai, Masanobu
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p. 435 - 442
(2007/10/02)
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- A New and Facile Method for the Direct Preparation of α-Hydroxycarboxylic Acid Esters from α,β-Unsaturated Carboxylic Acid Esters with Molecular Oxygen and Phenylsilane Catalyzed by Bis(dipivaloylmethanato)manganese(II) Complex
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In the presence of a catalytic amount of bis(dipivaloylmethanato)manganese(II) complex, the oxygenation of benzyl crotonate with molecular oxygen and phenylsilane proceeds smoothly under a mild condition to give benzyl 2-hydroxybutyrate in high yield.The reaction provides a new and convenient method for the direct preparation of various α-hydroxycarboxylic acid esters starting from α,β-unsaturated carboxylic acid esters.The influence of substituents of olefins on regioselectivity is also studied.
- Inoki, Satoshi,Kato, Koji,Isayama, Shigeru,Mukaiyama, Teruaki
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p. 1869 - 1872
(2007/10/02)
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