- Harnessing Stereospecific Z-Enamides through Silver-Free Cp?Rh(III) Catalysis by Using Isoxazoles as Masked Electrophiles
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The stereospecific synthesis of Z-enamides is described in this paper. For the first time, isoxazoles have been employed as electrophiles in C-H functionalization to afford thermodynamically less stable Z-enamides utilizing salicylaldehydes in an atom- and step-economic fashion. The stereochemistry of enamides might originate from the relative disposition of atoms present in isoxazole and the intramolecular hydrogen bonding. The reaction showed excellent scope as several structurally and electronically diverse salicylaldehydes and isoxazoles reacted efficiently.
- Debbarma, Suvankar,Bera, Sourav Sekhar,Maji, Modhu Sudan
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supporting information
p. 835 - 839
(2019/01/26)
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- Synthesis of isoflavones by tandem demethylation and ring-opening/cyclization of methoxybenzoylbenzofurans
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The unexpected conversion of benzoylbenzofurans into isoflavones through an intramolecular cascade that involves deprotection and ring-opening/cyclization is described. This was discovered in an investigation of the possible transformation of benzoylbenzofurans into coumaronochromones. This route affords isoflavones in two major steps from acetophenones and benzoquinones. The transformation was validated by synthesizing differently substituted isoflavone derivatives and further applied to a concise synthesis of a potential anticancer lead compound, glaziovianin A (1).
- Kunyane, Phaladi,Sonopo, Molahlehi S.,Selepe, Mamoalosi A.
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supporting information
p. 3074 - 3082
(2019/11/19)
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- Discovery and structure-activity relationships study of novel thieno[2,3-b]pyridine analogues as hepatitis C virus inhibitors
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Current treatment for hepatitis C is barely satisfactory, there is an urgent need to develop novel agents for combating hepatitis C virus infection. This study discovered a new class of thieno[2,3-b]pyridine derivatives as HCV inhibitors. First, a hit compound characterized by a thienopyridine core was identified in a cell-based screening of our privileged small molecule library. And then, structure activity relationship study of the hit compound led to the discovery of several potent compounds without obvious cytotoxicity in vitro (12c, EC50 = 3.3 μM, SI >30.3, 12b, EC50 = 3.5 μM, SI >28.6, 10l, EC50 = 3.9 μM, SI >25.6, 12o, EC 50 = 4.5 μM, SI >22.2, respectively). Although the mechanism of them had not been clearly elucidated, our preliminary optimization of this class of compounds had provided us a start point to develop new anti-HCV agents.
- Wang, Ning-Yu,Zuo, Wei-Qiong,Xu, Ying,Gao, Chao,Zeng, Xiu-Xiu,Zhang, Li-Dan,You, Xin-Yu,Peng, Cui-Ting,Shen, Yang,Yang, Sheng-Yong,Wei, Yu-Quan,Yu, Luo-Ting
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supporting information
p. 1581 - 1588
(2014/03/21)
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- Facile synthesis of 6-aryl-3-cyanopyridine-2-(1H)-thiones from aryl ketones
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An improved synthesis of 6-aryl-3-cyanopyridine-2-(1H)-thiones utilizing enaminones as starting materials catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) was described. Moreover, a convenient one-pot conversion of aryl ketones to 6-aryl-3-cyanopyridine-2-(1H)-thiones was also developed in moderate to good yields (up to 80%). Copyright Taylor & Francis Group, LLC.
- Zheng, Ren-Lin,Zeng, Xiu-Xiu,He, Hai-Yun,He, Jun,Yang, Sheng-Yong,Yu, Luo-Ting,Yang, Li
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experimental part
p. 1521 - 1531
(2012/04/17)
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- Novel thienopyridine derivatives as specific anti-hepatocellular carcinoma (HCC) agents: Synthesis, preliminary structure-activity relationships, and in vitro biological evaluation
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Novel thienopyridine derivatives 1b-1r were synthesized, based on a hit compound 1a that was found in a previous cell-based screening of anticancer drugs. Compounds 1a-1r have the following features: (1) their anticancer activity in vitro was first reported by our group. (2) The most potent analog 1g possesses hepatocellular carcinoma (HCC)-specific anticancer activity. It can specifically inhibit the proliferation of the human hepatoma HepG2 cells with an IC50 value of 0.016 μM (compared with doxorubicin as a positive control, whose IC50 was 0.37 μM). It is inactive toward a panel of five different types of human cancer cell lines. (3) Compound 1g remarkably induces G0/G1 arrest and apoptosis in HepG2 cells in vitro at low micromolar concentrations. These results, especially the HCC-specific anticancer activity of 1g, suggest their potential in targeted chemotherapy for HCC.
- Zeng, Xiu-Xiu,Zheng, Ren-Lin,Zhou, Tian,He, Hai-Yun,Liu, Ji-Yan,Zheng, Yu,Tong, Ai-Ping,Xiang, Ming-Li,Song, Xiang-Rong,Yang, Sheng-Yong,Yu, Luo-Ting,Wei, Yu-Quan,Zhao, Ying-Lan,Yang, Li
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supporting information; experimental part
p. 6282 - 6285
(2010/12/18)
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- 6-Aryl-pyrazolo[3,4-b]pyridines: Potent inhibitors of glycogen synthase kinase-3 (GSK-3)
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A novel series of 6-aryl-pyrazolo[3,4-b]pyridines has been identified that are potent inhibitors of glycogen synthase kinase-3 (GSK-3).
- Witherington, Jason,Bordas, Vincent,Gaiba, Alessandra,Garton, Neil S.,Naylor, Antoinette,Rawlings, Anthony D.,Slingsby, Brian P.,Smith, David G.,Takle, Andrew K.,Ward, Robert W.
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p. 3055 - 3057
(2007/10/03)
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