- A Bioinspired Synthesis of Polyfunctional Indoles
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Polyfunctional indoles bearing substituents at C5 and C6 are prevalent in natural products, pharmaceuticals, agrochemicals, and materials. Owing to the remoteness of the C5 and C6 positions, indoles of this family can be difficult to prepare, and often require multistep syntheses. Herein, we describe a concise process that converts simple derivatives of tyrosine into 5,6-difunctionalized indoles by direct oxidation of C?H, N?H, and O?H bonds. Our work draws inspiration from the biosynthetic polymerization of tyrosine to make melanin pigments, but makes an important departure to provide well-defined indole heterocycles.
- Huang, Zheng,Kwon, Ohhyeon,Huang, Haiyan,Fadli, Aziz,Marat, Xavier,Moreau, Magali,Lumb, Jean-Philip
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supporting information
p. 11963 - 11967
(2018/09/11)
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- Design, synthesis and evaluation of dual pharmacology β2- adrenoceptor agonists and PDE4 inhibitors
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A novel series of formoterol-phthalazinone hybrids were synthesised and evaluated as dual pharmacology β2-adrenoceptor agonists and PDE4 inhibitors. Most of the hybrids displayed high β2-adrenoceptor agonist and moderate PDE4 inhibitory activities. The most potent compound, (R,R)-11c, exhibited agonist (EC50 = 1.05 nM, pEC50 = 9.0) and potent PDE4B2 inhibitory activities (IC50 = 0.092 μM).
- Huang, Ling,Shan, Wenjun,Zhou, Qi,Xie, Jiaxing,Lai, Kefang,Li, Xingshu
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p. 249 - 253
(2014/01/17)
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- Synthesis and preliminary evaluation of (R,R)(S,S) 5-(2-(2-[4-(2-[18F]fluoroethoxy)phenyl]-1-methylethylamino)- 1-hydroxyethyl)-benzene-1,3-diol ([18F]FEFE) for the in vivo visualisation and quantification of the β2-adrenergic receptor status in lung
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The 18F-labeled β2-adrenergic receptor ligand (R,R)(S,S) 5-(2-(2-[4-(2-[18F]fluoroethoxy)phenyl]-1-methylethylamino)- 1-hydroxyethyl)-benzene-1,3-diol, a derivative of the original highly selective racemic fenoterol, was synthesized in an overall radiochemical yield of 20% after 65 min with a radiochemical purity higher than 98%. The specific activity was in the range of 50-60 GBq/μmol. In vitro testing of the non-radioactive fluorinated fenoterol derivative with isolated guinea pig trachea was conducted to obtain an IC50 value of 60 nM. Preliminary ex vivo organ distribution and in vivo experiments with positron emission tomography (PET) on guinea pigs were performed to study the biodistribution as well as the displacement of the radiotracer to prove specific binding to the β2-receptor.
- Schirrmacher, Esther,Schirrmacher, Ralf,Thews, Oliver,Dillenburg, Wolfgang,Helisch, Andreas,Wessler, Ignatz,Buhl, Roland,Hoehnemann, Sabine,Buchholz, Hans-Georg,Bartenstein, Peter,Machulla, Hans-Juergen,Roesch, Frank
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p. 2687 - 2692
(2007/10/03)
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- Synthesis of [18F]-Fluoroethylfenoterol for Imaging &β2 Receptor Status in Lung In Vivo
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5-(2-{2-[4-(2-[18F]fluoroethoxy)-phenyl]-1-methyl-ethylamino}-1-hydroxy-ethyl)-benzene-1,3-diol ([18F]fluoroethylfenoterol) was synthesised from 4-(2-{benzyl-[2-(3,5-bis-benzyloxy-phenyl)-2-hydroxy-ethyl]-amino}-propyl)-phenol using 2-[18F]fluoroethyltosylate (92 percent RCY) followed by reductive cleavage of the benzyl protecting groups. Preliminary in vitro tests showed [19F]fluoroethylfenoterol to be as potent in relaxation of lung tissue as fenoterol itself.
- Schirrmacher, E.,Schirrmacher, R.,Buhl, R.,Wessler, I.,Machulla, H.-J.,Roesch, F.
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p. S436 - S438
(2007/10/03)
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