- Betti reaction enables efficient synthesis of 8-hydroxyquinoline inhibitors of 2-oxoglutarate oxygenases
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There is interest in developing potent, selective, and cell-permeable inhibitors of human ferrous iron and 2-oxoglutarate (2OG) oxygenases for use in functional and target validation studies. The 3-component Betti reaction enables efficient one-step C-7 functionalisation of modified 8-hydroxyquinolines (8HQs) to produce cell-active inhibitors of KDM4 histone demethylases and other 2OG oxygenases; the work exemplifies how a template-based metallo-enzyme inhibitor approach can be used to give biologically active compounds.
- Thinnes,Tumber,Yapp,Scozzafava,Yeh,Chan,Tran,Hsu,Tarhonskaya,Walport,Wilkins,Martinez,Müller,Pugh,Ratcliffe,Brennan,Kawamura,Schofield
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supporting information
p. 15458 - 15461
(2015/10/20)
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- Synthesis of 8-hydroxyquinolines with amino and thioalkyl functionalities at position 4
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(Chemical Equation Presented) Six 8-hydroxyquinolines with amino and thioalkyl functionalities at position 4 have been prepared. The synthesis starts with chlorination of the readily available 4-hydroxy-8-tosyloxyquinoline to give 4-chloro-8-tosyloxyquinoline in 94% yield. Treatment of the 4-chloro-8-tosyloxyquinoline with sulphur and nitrogen nucleophiles produces the target 4-amino and 4-thioalkyl-8-hydroxyquinolines in more than 70% yield. In case of sulphur nucleophiles and pyrrolidine, the removal of the protecting tosyl group at position 8 occurs simultaneously with the substitution of chlorine at position 4.
- Omar, Walaa A. E.,Heiskanen, Juha P.,Hormi, Osmo E. O.
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p. 593 - 595
(2008/09/19)
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- Synthesis of 4-[4-(N,N-dimethylsulfamoyl)piperazin-1-yl]-quinolines derivatives as sorbitol dehydrogenase potential inhibitors
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Synthesis of various quinolines, substituted in position 4 by [4-(N,N-dimethylsulfamoyl)piperazin-1-yl] group and in position 2 by different groups such as hydrogen, methyl, hydroxymethyl, formyl or carboxyl is described. Besides, we have synthesized derivatives of 8-hydroxyquinoline.
- Varlet, Didier,Fourmaintraux, Eric,Depreux, Patrick,Lesieur, Daniel
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p. 385 - 396
(2007/10/03)
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- Quinoline derivatives as immunostimulants
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This invention relates to compounds of the formula STR1 wherein R1, R2, R3, R4, R5, R6 and R7 are as defined hereinbelow that exhibit activity as immunostimulants.
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- Improved Syntheses of Some Monohloro- and Monobromo-8-quinolinols
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Procedures were developed for the preparation of the 2-, 3-, 4-, and 6-monosubstituted chloro and bromo 8-quinolinols which afforded greater yields and/or reduced the number of steps in the preparation. 100 MHz 1H-NMR spetra for the 12 possible monochloro
- Gershon, Herman,Clarke, Donald D.
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p. 935 - 942
(2007/10/02)
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- 4-(Dimethylamino)-8-hydroxyquinoline as a new Chelating Ligand and as a Donor-enforced Terminal Group in Podands
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Electron releasing and -withdrawing substituents are introduced into the 4-position of 8-hydroxy-quinoline (oxine) (1), starting with 4-chloro-8-methoxyquinoline (2).The UV/Vis spectra of the oxines 4, 5 and their Ni-, Cu-, and Co-complexes are compared with those of oxine.Intensity increases of the long wave length absorptions are observed with the new ligand 4 compared to oxine itself and with the metal complexes.The substituted oxines are also used as new donor end groups in podands 8-12.The ammonium complexes of the new podands are investigated.
- Voegtle, Fritz,Siebert, Axel
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p. 1556 - 1563
(2007/10/02)
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