- Identification of an Oxalamide Ligand for Copper-Catalyzed C?O Couplings from a Pharmaceutical Compound Library
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A typical pharmaceutical compound library is stocked with molecular diversity and could provide a platform for the discovery of new ligand structures. Herein, we describe the use of this approach in combination with high throughput screening to identify N,N’-bis(thiophene-2-ylmethyl)oxalamide as a ligand that is generally effective for copper-catalyzed C?O cross-couplings to prepare both biarylethers as well as phenols under mild conditions.
- Chan, Vincent S.,Krabbe, Scott W.,Li, Changfeng,Sun, Lijie,Liu, Yue,Nett, Alex J.
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- Para-Selective Cu-Catalyzed C-H Aryloxylation of Electron-Rich Arenes and Heteroarenes
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Cu-catalyzed reaction of phenols with electron-rich arene or heteroarene ligands of unsymmetrical diaryl-λ3-iodanes is a key step in the developed one-pot two-step method for intermolecular para-selective C-H aryloxylation of heteroarenes and arenes.
- Sokolovs, Igors,Suna, Edgars
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p. 371 - 379
(2016/01/25)
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- CsF/clinoptilolite: An efficient solid base in SNAr and copper-catalyzed Ullmann reactions
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CsF/clinoptilolite was found to be an efficient solid base catalyst for both SNAr and Ullmann ether reactions. A general and efficient one-step procedure was developed for the synthesis of biaryl ethers via direct coupling of electron-deficient aryl halides to phenols using CsF/clinoptilolite. The protocol was also applied to electron-rich aryl halides by addition of a catalytic amount of copper oxide nanoparticles. Both SNAr and Ullmann reactions were rapid and provided good to excellent yields.
- Keipour, Hoda,Hosseini, Abolfazl,Afsari, Amir,Oladee, Razieh,Khalilzadeh, Mohammad A.,Ollevier, Thierry
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- Evaluation of Novel N-(piperidine-4-yl)benzamide Derivatives as Potential Cell Cycle Inhibitors in HepG2 Cells
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In this study, a series of novel N-(piperidine-4-yl)benzamide derivatives was designed, synthesized, and evaluated for antitumor activity. Some compounds were found to have potent antitumor activity. In particular, compound 47 showed the most potent biological activity against HepG2 cells, with an IC50 value of 0.25 μm. Western blot analysis demonstrated that compound 47 inhibited the expression of cyclin B1 and p-Rb and enhanced the expression of p21, p53, Rb, and phospho-adenosine monophosphate-activated protein kinase (p-AMPK). Further, cell cycle arrest was observed by flow cytometry (FCM). In summary, compound 47 was screened to have potential activity for the treatment of hepatocarcinoma via the induction of cell cycle arrest by a p53/p21-dependent pathway.
- Hou, Jin,Zhao, Wei,Huang, Zhi-Ning,Yang, Shao-Mei,Wang, Li-Juan,Jiang, Yu,Zhou, Zhong-Shi,Zheng, Man-Yi,Jiang, Ji-Li,Li, Shan-Hua,Li, Fu-Nan
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p. 223 - 231
(2015/11/24)
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- COMPOUNDS FOR TREATING VIRAL INFECTIONS
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The present invention relates to small molecule compounds and their use in the treatment of diseases, in particular viral diseases, in particular hepatitis C virus (HCV).
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Page/Page column 91
(2015/11/09)
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- P(i-BuNCH2CH2)3N: an efficient promoter for the microwave synthesis of diaryl ethers
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With the title proazaphosphatrane as a promoter, the coupling of aryl fluorides with aryl TBDMS ethers under microwave conditions gave moderate to high yields of the desired products at low catalyst loadings and in short times. In this methodology, electron deficient aryl fluorides possessing substituents, such as nitro, cyano, and ester, were coupled with sterically demanding aryl TBDMS ethers as well as with aryl TBDMS ethers bearing a variety of functionalities such as methoxy, halo, and cyano groups.
- Raders, Steven M.,Verkade, John G.
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p. 3507 - 3511
(2008/09/21)
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- Synthesis of novel diaryl ethers and their evaluation as antimitotic agents
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A series of novel diaryl ethers possessing various functional groups were synthesized and evaluated for antiproliferative activity in human myeloid leukemia HL-60 cells. Among the compounds examined, compounds 10, 17, 20, 24, and 33 showed moderate to pot
- In, Jin-Kyung,Lee, Mi-Sung,Yang, Jung-Eun,Kwak, Jae-Hwan,Lee, Heesoon,Boovanahalli, Shanthaveerappa K.,Lee, Kyeong,Kim, Soo Jin,Moon, Seung Kee,Lee, Sungsook,Choi, Nam Song,Ahn, Soon Kil,Jung, Jae-Kyung
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p. 1799 - 1802
(2007/10/03)
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- P(i-BuNCH2CH2)3N: An efficient promoter for the nucleophilic aromatic substitution reaction of aryl fluorides with aryl TBDMS (or TMS) ethers
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(Chemical Equation Presented) The nucleophilic aromatic substitution reaction between electron-deficient aryl fluorides and aryl TBDMS (or TMS) ethers has been shown to be efficiently promoted by proazaphosphatranes such as P(i-BuNCH2CH2)3N (3). Excellent yields of diaryl ether products were obtained under unusually mild conditions.
- Urgaonkar, Sameer,Verkade, John G.
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p. 3319 - 3322
(2007/10/03)
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- Catalytic activation of silylated nucleophiles using tBu-P4 as a base
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Trialkylsilyl groups play an important role as effective protecting groups in organic synthesis. Various O, N, and C nucleophilic sites can be protected by trialkylsilyl groups to control the selectivity of reactions. The nucleophilic attack of a fluoride anion on a silyl group is recognized as one of the most useful methods for desilylation. The activation of the nucleophile-silicon bond is important not only for desilylation but also for the generation of a reactive nucleophilic anion to achieve a new bond formation. The phosphazene bases developed by Schwesinger are known to be strong non-metallic organic bases. Among them, the tBu-P4 base has been used for various selective deprotonative transformations, although the ability of tBu-P4 base to activate silylated nucleophiles has not yet been shown. A novel catalytic activation of various O, N, and C nucleophile-silicon bonds using tBu-P4 base was investigated to perform nucleophilic reactions with various electrophiles. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
- Ueno, Masahiro,Hori, Chieko,Suzawa, Koichi,Ebisawa, Masashi,Kondo, Yoshinori
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p. 1965 - 1968
(2007/10/03)
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- Triaryl-oxy-aryloxy-pyrimidine-2,4,6-trione metalloproteinase inhibitors
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The present invention relates to triaryl-oxy-aryloxy-pyrimidine-2,4,6-trione; metalloproteinase inhibitors of the formula wherein X, A, Y, B, G, W, and R1 are as defined in the specification, and to pharmaceutical compositions and methods of treating inflammation, cancer and other disorders.
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Page/Page column 37
(2010/02/05)
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