- Aerobic C-H acetoxylation of 8-methylquinoline in PdII- pyridinecarboxylic acid systems: Some structure-reactivity relationships
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Catalytic oxidative C-H acetoxylation of 8-methylquinoline as a model substrate with O2 as oxidant was performed using palladium(II) carboxylate catalysts derived from four different pyridinecarboxylic acids able to form palladium(II) chelates of different size. A comparison of the rates of the substrate C-H activation and the O2 activation steps shows that the C-H activation step is rate-limiting, whereas the O2 activation occurs at a much faster rate already at 20 C. The chelate ring size and the chelate ring strain of the catalytically active species are proposed to be the key factors affecting the rate of the C-H activation.
- Wang, Daoyong,Zavalij, Peter Y.,Vedernikov, Andrei N.
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- Monodisperse CuPd alloy nanoparticles supported on reduced graphene oxide as efficient catalyst for directed C?H activation
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The palladium-catalyzed selective activation of C–H bonds is of great importance for the construction of diverse bioactive molecules. Herein, monodisperse CuPd alloy nanoparticles supported on reduced graphene oxide have been used as high efficient and re
- Wang, Feifan,Huang, Fei,Yu, Yingliang,Zhou, Shuangliu,Wang, Zhenghua,Zhang, Wu
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- Multi-Functional Oxidase Activity of CYP102A1 (P450BM3) in the Oxidation of Quinolines and Tetrahydroquinolines
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Tetrahydroquinoline, quinoline, and dihydroquinolinone are common core motifs in drug molecules. Screening of a 48-variant library of the cytochrome P450 enzyme CYP102A1 (P450BM3), followed by targeted mutagenesis based on mutation-selectivity correlations from initial hits, has enabled the hydroxylation of substituted tetrahydroquinolines, quinolines, and 3,4-dihydro-2-quinolinones at most positions around the two rings in good to high yields at synthetically relevant scales (1.5 g L?1 day?1). Other oxidase activities, such as C?C bond desaturation, aromatization, and C?C bond formation, were also observed. The enzyme variants, with mutations at the key active site residues S72, A82, F87, I263, E267, A328, and A330, provide direct and sustainable routes to oxy-functionalized derivatives of these building block molecules for synthesis and drug discovery.
- Li, Yushu,Wong, Luet L.
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p. 9551 - 9555
(2019/08/06)
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- Palladium-Catalyzed C-H Bond Functionalization Reactions Using Phosphate/Sulfonate Hypervalent Iodine Reagents
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A new and operationally simple approach for palladium-catalyzed C-H functionalization reactions utilizing an organophosphorus/sulfonate hypervalent iodine reagent as both an oxidant and the source of a functional group has been developed. Through this method, the oxidative phosphorylation-, sulfonation-, and hydroxylation of unactivated benzyl C(sp3)-H bonds, along with the hydroxylation and arylation of aryl C(sp2)-H bonds, are successfully realized under mild conditions and with excellent site-selectivity. The versatile C-OSO2R bond provides a platform for a wide array of subsequent diversification reactions.
- He, Yimiao,Huang, Lilan,Xie, Limei,Liu, Peng,Wei, Qiongmei,Mao, Fangfang,Zhang, Xuehong,Huang, Jun,Chen, Sijing,Huang, Chusheng
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p. 10088 - 10101
(2019/08/22)
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- Catalytic C(sp3)?H Arylation of Free Primary Amines with an exo Directing Group Generated In Situ
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Herein, we report the palladium-catalyzed direct arylation of unactivated aliphatic C?H bonds in free primary amines. This method takes advantage of an exo-imine-type directing group (DG) that can be generated and removed in situ. A range of unprotected aliphatic amines are suitable substrates, undergoing site-selective arylation at the γ-position. Methyl as well as cyclic and acyclic methylene groups can be activated. Furthermore, when aniline-derived substrates were used, preliminary success with δ-C?H arylation was achieved. The feasibility of using the DG component in a catalytic fashion was also demonstrated.
- Xu, Yan,Young, Michael C.,Wang, Chengpeng,Magness, David M.,Dong, Guangbin
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supporting information
p. 9084 - 9087
(2016/07/26)
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- Synthesis and anti-norovirus activity of pyranobenzopyrone compounds
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During the last decade, noroviruses have gained media attention as the cause of large scale outbreaks of gastroenteritis on cruise ships, dormitories, nursing homes, etc. Although noroviruses do not multiply in food or water, they can cause large outbreaks because approximately 10-100 virions are sufficient to cause illness in a healthy adult. Recently, it was shown that the activity of acyl-coenzyme A:cholesterol acyltransferase-1 (ACAT1) enzyme may be important in norovirus infection. In search of anti-noroviral agents based on the inhibition of ACAT1, we synthesized and evaluated the inhibitory activities of a class of pyranobenzopyrone molecules containing amino, pyridine, substituted quinolines, or 7,8-benzoquinoline nucleus. Three of the sixteen evaluated compounds possess ED50 values in the low micrometer range. 2-Quinolylmethyl derivative 3A and 4-quinolylmethyl derivative 4A showed ED50 values of 3.4 and 2.4 μM and TD50 values of >200 and 96.4 μM, respectively. The identified active compounds are suitable for further modification for the development of anti-norovirus agents.
- Pokhrel, Laxman,Kim, Yunjeong,Nguyen, Thi D.T.,Prior, Allan M.,Lu, Jianyu,Chang, Kyeong-Ok,Hua, Duy H.
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supporting information; experimental part
p. 3480 - 3484
(2012/07/03)
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- Catalytic aerobic oxidation of substituted 8-methylquinolines in Pd II-2,6-pyridinedicarboxylic acid systems
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The ability of PdII complexes derived from 2,6- pyridinedicarboxylic acids to catalyze homogeneous regioselective aerobic oxidation of 5- and 6-substituted 8-methylquinolines in AcOH-Ac2O solution to produce corresponding 8-quinolylm
- Zhang, Jing,Khaskin, Eugene,Anderson, Nicholas P.,Zavalij, Peter Y.,Vedernikov, Andrei N.
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supporting information; body text
p. 3625 - 3627
(2009/02/06)
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- 2,4-DIAMINOQUINAZOLINES FOR SPINAL MUSCULAR ATROPHY
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2,4-Diaminoquinazolines of formulae I-IV and VI (I, II, III, IV and VI) are useful for treating spinal muscular atrophy (SMA).
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Page/Page column 73-74
(2010/02/15)
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- Quinoline derivatives and medicinal use thereof
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A quinoline derivative represented by the following formula (1): allows PPARα or γ which is an intranuclear transcription factor, to function strongly and is low in toxicity. By using this compound as an active ingredient, there can be provided a preventive or therapeutic agent for various diseases related to PPARα or γ.
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- Benzimidazolyl-sulfinyl-tetrahydroquinolines
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A hydroquinoline compound of the formula (1): STR1 wherein R1, R2, R3, A, l, m and n are as defined or its pharmaceutically acceptable salt, composition containing the compound and processes for preparing same are disclosed. The compound is useful as an antiulcer agent.
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- ELECTRONIC NATURE OF THE AZA SUBSTITUENT OF PYRIDYL AND QUINOLYL GROUPS FOR REACTIVITIES IN AN INSULATED SYSTEM
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A new set of ?0 values was determined for all positions of pyridyl and quinolyl groups, reliably excluding steric effect by perihydrogen, on the basis of the rates of the alkaline hydrolysis of substituted 2-methylbenzoates and pyridylmethyl and quinolylmethyl 2-methyl-benzoates in 70percent aq acetone.
- Sawada, Masami,Ichihara, Masaharu,Ando, Takashi,Yukawa, Yasuhide,Tsuno, Yuho
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p. 4917 - 4920
(2007/10/02)
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