- Copper-catalyzed recycling of halogen activating groups via 1,3-halogen migration
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A Cu(I)-catalyzed 1,3-halogen migration reaction effectively recycles an activating group by transferring bromine or iodine from a sp2 to a benzylic carbon with concomitant borylation of the Ar-X bond. The resulting benzyl halide can be reacted in the same vessel under a variety of conditions to form an additional carbon-heteroatom bond. Cross-over experiments using an isotopically enriched bromide source support intramolecular transfer of Br. The reaction is postulated to proceed via a Markovnikov hydrocupration of the o-halostyrene, oxidative addition of the resulting Cu(I) complex into the Ar-X bond, reductive elimination of the new sp3 C-X bond, and final borylation of an Ar-Cu(I) species to turn over the catalytic cycle.
- Grigg, R. David,Van Hoveln, Ryan,Schomaker, Jennifer M.
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p. 16131 - 16134,4
(2020/09/09)
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- NOVEL ACYL GUANIDINE DERIVATIVES
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The present invention provides a pharmaceutical which possesses an excellent inhibitory effect on NHE3 (Na+/H+ exchanger type 3) and effectively improves diseases or conditions of organs in which NHE3 is expressed.
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- Synthesis and biological studies of novel 2-aminoalkylethers as potential antiarrhythmic agents for the conversion of atrial fibrillation
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A series of 2-aminoalkylethers prepared as potential antiarrhythmic agents is described. The present compounds are mixed sodium and potassium ion channel blockers and exhibit antiarrhythmic activity in a rat model of ischemia-induced arrhythmias. Structure-activity studies led to the identification of three compounds 5, 18, and 26, which were selected based on their particular in vivo electrophysiological properties, for studies in two canine atrial fibrillation (AF) models. The three compounds converted AF in both models, but only compound 26 was shown to be orally bioavailable. Resolution of the racemate 26 into its corresponding enantiomers 40 and 41 and subsequent biological testing of these enantiomers led to the selection of (1S,2S)-1-(1-naphthalenethoxy)-2-(3- ketopyrrolidinyl)cyclohexane monohydrochloride (41) as a potential atrial selective antiarrhythmic candidate for further development.
- Plouvier, Bertrand,Beatch, Gregory N.,Jung, Grace L.,Zolotoy, Alexander,Sheng, Tao,Clohs, Lilian,Barrett, Terrance D.,Fedida, David,Wang, Wei Q.,Zhu, Jeff J.,Liu, Yuzhong,Abraham, Shlomo,Lynn, Leah,Dong, Ying,Wall, Richard A.,Walker, Michael J. A.
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p. 2818 - 2841
(2008/02/09)
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- Synthesis, absorption and luminescence of a new series of soluble distyrylbenzenes featuring cyano substituents at the peripheral rings
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The synthesis of a complete series of nine soluble distyrylbenzenes (DSBs) with two (2a-c) and four cyano groups (1a-f) attached to the peripheral aromatic rings is reported. They were prepared by the Wittig reaction and characterized by 1H and 13C NMR, FT-IR, UV/Vis, PL, EL, mass spectra, and elemental analysis. The optical properties have been studied in detail to monitor structure-luminescence relationships as a function of the position of the cyano moieties. The DSBs with cyano substituents show bathochromic shifts in their absorption spectra when compared to the parent DSB (30). The extent of this red-shift depends on electronic and steric factors. The bis(p-cyano)-substituted compound 2c exhibits a small Stokes shift and a remarkably high quantum yield of ψF = 0.6-0.8 in the solid state. All the new distyrylbenzenes show electroluminescence when employed in devices with an ITO/PcCu/DSB/Al configuration and with colors ranging from red to green.
- Schweikart, Karl-Heinz,Hanack, Michael,Lueer, Larry,Oelkrug, Dieter
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p. 293 - 302
(2007/10/03)
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