- Carbon isotope labeling of carbamates by late-stage [11C], [13C] and [14C]carbon dioxide incorporation
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A general procedure for the late-stage [11C], [13C] and [14C]carbon isotope labeling of cyclic carbamates is reported. This protocol allows the incorporation of carbon dioxide, the primary source of carbon-14 and carbon-11 radioisotopes, in a direct, cost-effective and sustainable manner. A disconnection/reconnection strategy, involving ring opening/isotopic closure, was also implemented.
- Del Vecchio, Antonio,Talbot, Alex,Caillé, Fabien,Chevalier, Arnaud,Sallustrau, Antoine,Loreau, Olivier,Destro, Gianluca,Taran, Frédéric,Audisio, Davide
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supporting information
p. 11677 - 11680
(2020/10/19)
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- Azacyclic derivative as well as preparation method and medical use thereof
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The invention relates to an azacyclic derivative as well as a preparation method and medical use thereof and particularly relates to an azacyclic derivative represented by a general formula (I) (shownin the description), a preparation method thereof, a pharmaceutical composition containing the derivative and use of the derivative as an SMO antagonist, particularly in the treatment of diseases such as cancer related to Hedgehog signal channels. The definitions of groups in the general formula (I) are same as the definitions in the description.
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Paragraph 0236; 0238; 0239
(2019/02/04)
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- Triazole-Based Inhibitors of the Wnt/β-Catenin Signaling Pathway Improve Glucose and Lipid Metabolisms in Diet-Induced Obese Mice
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Wnt/β-catenin signaling pathway is implicated in the etiology and progression of metabolic disorders. Although lines of genetic evidence suggest that blockage of this pathway yields favorable outcomes in treating such ailments, few inhibitors have been used to validate the promising genetic findings. Here, we synthesized and characterized a novel class of triazole-based Wnt/β-catenin signaling inhibitors and assessed their effects on energy metabolism. One of the top inhibitors, compound 3a, promoted Axin stabilization, which led to the proteasome degradation of β-catenin and subsequent inhibition of the Wnt/β-catenin signaling in cells. Treatment of hepatocytes and high fat diet-fed mice with compound 3a resulted in significantly decreased hepatic lipid accumulation. Moreover, compound 3a improved glucose tolerance of high fat diet-fed mice without noticeable toxicity, while downregulating the genes involved in the glucose and fatty acid anabolisms. The new inhibitors are expected to be further developed for the treatment of metabolic disorders.
- Obianom, Obinna N.,Ai, Yong,Li, Yingjun,Yang, Wei,Guo, Dong,Yang, Hong,Sakamuru, Srilatha,Xia, Menghang,Xue, Fengtian,Shu, Yan
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p. 727 - 741
(2019/01/21)
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- Gold-catalyzed cyclization of 1-(2′-Azidoaryl) propynols: Synthesis of polysubstituted 4-quinolones
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An unprecedented gold-catalyzed procedure for the synthesis of polysubstituted 4-quinolones from 1-(2′-Azidoaryl) propynols is described. The reaction undergoes an intramolecular nucleophilic attack of the azide group to the Au-Activated triple bonds in a 6-endo-dig manner and subsequent gold-Assisted expulsion of N2 to furnish an α-imino gold carbene intermediate, which triggers a 1,2-carbon migration and finally is converted to 2,3-disubstituted 4-quinolone.
- Wu, Xiang,Zheng, Lang-Lang,Zhao, Li-Ping,Zhu, Cheng-Feng,Li, You-Gui
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supporting information
p. 14769 - 14772
(2019/12/24)
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- Synthesis of novel 1,2,3-triazole based artemisinin derivatives and their antiproliferative activity
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Two series of novel 1,2,3-triazole based artemisinin derivatives were designed, synthesized via a copper(i)-catalyzed azide alkyne cycloaddition (CuAAC) reaction and investigated for their antiproliferative activity by MTT assay against various human canc
- Kapkoti, Deepak Singh,Singh, Shilpi,Luqman, Suaib,Bhakuni, Rajendra Singh
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p. 5978 - 5995
(2018/04/23)
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- Handling Hazards Using Continuous Flow Chemistry: Synthesis of N1-Aryl-[1,2,3]-triazoles from Anilines via Telescoped Three-Step Diazotization, Azidodediazotization, and [3 + 2] Dipolar Cycloaddition Processes
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The conversion of commercially available anilines into triazole products was realized using a telescoped three-reactor flow diazotization, azidodediazotization, and [3 + 2] dipolar cycloaddition process. The diazotization-azidodediazotization sequence was
- Teci, Matthieu,Tilley, Michael,McGuire, Michael A.,Organ, Michael G.
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supporting information
p. 1967 - 1973
(2017/02/10)
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- A library of 1,2,3-triazole-substituted oleanolic acid derivatives as anticancer agents: Design, synthesis, and biological evaluation
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A series of novel oleanolic acid coupled 1,2,3-triazole derivatives have been designed and synthesized by employing a Cu(i) catalyzed Huisgen 1,3-dipolar cycloaddition reaction. The anti-proliferative evaluation indicated that some compounds exhibited exc
- Wei, Gaofei,Luan, Weijing,Wang, Shuai,Cui, Shanshan,Li, Fengran,Liu, Yongxiang,Liu, Yang,Cheng, Maosheng
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p. 1507 - 1514
(2015/01/30)
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- One-pot, two-step cascade synthesis of quinazolinotriazolobenzodiazepines
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An operationally simple, one-pot, two-step cascade method has been developed to afford quinazolino[1,2,3]triazolo[1,4]benzodiazepines. This unique, atom-economical transformation engages five reactive centers (amide, aniline, carbonyl, azide, and alkyne) and employs environmentally benign iodine as a catalyst. The method proceeds via sequential quinazolinone-forming condensation and intramolecular azide-alkyne 1,3-dipolar cycloaddition reactions. Substrate scope, multicomponent examples, and mechanistic insights are discussed.
- Guggenheim, Kathryn G.,Toru, Hannah,Kurth, Mark J.
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supporting information; scheme or table
p. 3732 - 3735
(2012/09/08)
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- Design, synthesis, and in vitro biological evaluation of 1 H -1,2,3-triazole-4-carboxamide derivatives as new anti-influenza A agents targeting virus nucleoprotein
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The influenza virus nucleoprotein (NP) is an emerging target for anti-influenza drug development. Nucleozin (1) and its closely related derivatives had been identified as NP inhibitors displaying anti-influenza activity. Utilizing 1 as a lead molecule, we successfully designed and synthesized a series of 1H-1,2,3-triazole-4-carboxamide derivatives as new anti-influenza A agents. One of the most potent compounds, 3b, inhibited the replication of various H3N2 and H1N1 influenza A virus strains with IC 50 values ranging from 0.5 to 4.6 μM. Compound 3b also strongly inhibited the replication of H5N1 (RG14), amantidine-resistant A/WSN/33 (H1N1), and oseltamivir-resistant A/WSN/1933 (H1N1, 274Y) virus strains with IC 50 values in sub-μM ranges. Further computational studies and mechanism investigation suggested that 3b might directly target influenza virus A nucleoprotein to inhibit its nuclear accumulation.
- Cheng, Huimin,Wan, Junting,Lin, Meng-I,Liu, Yingxue,Lu, Xiaoyun,Liu, Jinsong,Xu, Yong,Chen, Jianxin,Tu, Zhengchao,Cheng, Yih-Shyun E.,Ding, Ke
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supporting information; experimental part
p. 2144 - 2153
(2012/05/04)
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- Flow synthesis of organic azides and the multistep synthesis of imines and amines using a new monolithic triphenylphosphine reagent
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Here we describe general flow processes for the synthesis of alkyl and aryl azides, and the development of a new monolithic triphenylphosphine reagent, which provides a convenient format for the use of this versatile reagent in flow. The utility of these new tools was demonstrated by their application to a flow Staudinger aza-Wittig reaction sequence. Finally, a multistep aza-Wittig, reduction and purification flow process was designed, allowing access to amine products in an automated fashion.
- Smith, Catherine J.,Smith, Christopher D.,Nikbin, Nikzad,Ley, Steven V.,Baxendale, Ian R.
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supporting information; experimental part
p. 1927 - 1937
(2011/04/21)
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- A fully automated, multistep flow synthesis of 5-amino-4-cyano-1,2,3- triazoles
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Having demonstrated in the preceding publication the flow synthesis of aryl azides, we describe here a general protocol for the in-line purification of these versatile intermediates. As part of this investigation, we evaluated the use of ReactIR 45m as a
- Smith, Catherine J.,Nikbin, Nikzad,Ley, Steven V.,Lange, Heiko,Baxendale, Ian R.
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supporting information; experimental part
p. 1938 - 1947
(2011/04/24)
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- Intramolecular Fe(II)-Catalyzed N-O or N-N bond formation from aryl azides
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(Figure presented) Iron(II) bromide catalyzes the transformation of aryl and vinyl azides with ketone or methyl oxime substituents into 2,1-benzisoxazoles, indazoles, or pyrazoles through the formation of an N-O or N-N bond. This transformation tolerates a variety of different functional groups to facilitate access to a range of benzisoxazoles or indazoles. The unreactivity of the Z-methyloxime indicates that N-heterocycle formation occurs through a nucleophilic attack of the ketone or oxime onto an activated planar iron azide complex.
- Stokes, Benjamin J.,Vogel, Carl V.,Urnezis, Linda K.,Pan, Minjie,Driver, Tom G.
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supporting information; experimental part
p. 2884 - 2887
(2010/08/21)
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- Pyrolysis of Aryl Azides. IX. Azomethines as Weak Neighbouring Groups
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The following rates of pyrolysis (relative to azidobenzene at 120 deg C) have been measured in decalin solution: 2-azidobenzaldehyde, 28.8; 2-azidobenzylideneaniline, 59.5; 2-azidobenzaldehyde phenylhydrazone, 8.9; 2-azidobenzaldehyde oxime O-methyl ether, 1.3; 2-azidoacetophenone oxime O-methyl ether, 23.4; 2-azidobenzophenone phenylhydrazone, 9.7.It is argued that these relative rates are largely determined by the extent to which the ortho substituent is in the reactive conformation for an electrocyclic process.Indazoles substituted on N2 are isolated from pyrolysis of those azides with ortho-azomethine substituents.
- Dyall, Leonard K.,Holmes, Ann-Louise
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p. 1677 - 1686
(2007/10/02)
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- 2,2-Disubstituted-1,2-dihydro-3H-indol-3-ones by Base- and Thermal-induced Cyclisations of o-Azidophenyl s-Alkyl Ketones and o-Azidobenzoyl Esters
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o-Azidophenyl s-alkyl ketones in ethanolic potassium hydroxide at room temperature undergo loss of nitrogen and cyclisation to 2,2-dialkyl-1,2-dihydro-3H-indol-3-ones in high yield.Kinetic data (E(act.) 62.4 and 71.6 kJ mol-1, respectively) obtained for the o-azidophenylisopropyl and o-azidophenylcyclohexyl ketones support an assisted nitrogen loss from the azide via the enolate ion, rather than a nitrene reaction. 1,2-Dihydro-3H-indol-3-ones, along with in some cases 2,1-benzisoxazoles, have been obtained by the thermolysis and spray vacuum pyrolysis of other o-azidophenyl alkyl ketones, diethyl o-azidobenzoyl malonate, and ethyl o- azidobenzoyl(phenyl)acetate.
- Azadi-Ardakani, Manouchehr,Alkhader, Mohamed A.,Lippiatt, John H.,Patel, Dalpat I.,Smalley, Robert K.,Higson, Susan
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p. 1107 - 1112
(2007/10/02)
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