- Chemoselectivity in the reactions between ethyl 4,4,4-trifluoro-3-oxobutanoate and anilines: Improved synthesis of 2-trifluoromethyl-4- and 4-trifluoromethyl-2-quinolinones
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Chemoselectivity in the reactions between ethyl 4,4, 4-trifluoroacetoacetate (ethyl 4,4,4-trifluoro-3-oxobutanoate) and various anilines was systematically studied as a function of the reaction conditions used (solvent/temperature, catalyst). The results obtained allowed chemoselective (>90%) synthesis of the corresponding ethyl 3-arylamino-4,4,4-trifluorobut-2-enoates and N-aryl-4,4,4-trifluoro-3-oxobutyramides, which were cyclized to afford 2-trifluoromethyl-4-quinolinones and 4-trifluoromethyl-2-quinolinones, respectively.
- Berbasov, Dmitrii O.,Soloshonok, Vadim A.
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- Discovery of 6-N,N-Bis(2,2,2-trifluoroethyl)amino-4- trifluoromethylquinolin-2(1H)-one as a novel selective androgen receptor modulator
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The androgen receptor is a member of the extended family of nuclear receptors and is widely distributed throughout the body. Androgen therapy is used to compensate for low levels of the natural hormones testosterone (T) and dihydrotestosterone and consist
- Van Oeveren, Arjan,Motamedi, Mehrnouch,Mani, Neelakandha S.,Marschke, Keith B.,López, Francisco J.,Schrader, William T.,Negro-Vilar, Andrés,Zhi, Lin
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- SUBSTITUTED AZOLE DIONE COMPOUNDS WITH ANTIVIRAL ACTIVITY
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Provided herein are methods of using substituted azole dione compounds for treatment of viral infections.
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Paragraph 00363; 00449
(2021/10/02)
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- INHIBITORS OF MALT1 AND USES THEREOF
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Provided herein are compounds that inhibit MALTl, a protein whose activity is responsible for constitutive NF-κΒ signaling in certain cancers (e.g., activated B-cell diffuse large B-cell lymphoma (ABC-DLBCL)). Also provided are pharmaceutical compositions and kits comprising the compounds, and methods of treating MALTl -related diseases and disorders (e.g., cancer) with the compounds in a subject, by administering the compounds and/or compositions described herein.
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Paragraph 00362
(2018/09/28)
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- Novel Sulfonaminoquinoline Hepcidin Antagonists
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The present invention relates to novel hepcidin antagonists, pharmaceutical compositions comprising them and the use thereof as medicaments for the use in the treatment of iron metabolism disorders, such as, in particular, iron deficiency diseases and anemias, in particular anemias in connection with chronic inflammatory diseases.
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Page/Page column 172
(2012/09/05)
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- Compounds with anti-cancer activity
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Novel substituted azole diones are provided that kill cells, suppress cell proliferation, suppress cell growth, abrogate the cell cycle G2 checkpoint and/or cause adaptation to G2 cell cycle arrest. Methods of making and using the invention compounds are provided. The invention provides substituted azole diones to treat cell proliferation disorders. The invention includes the use of substituted azole diones to selectively kill or suppress cancer cells without additional anti-cancer treatment. The invention includes the use of cell cycle G2-checkpoint-abrogating substituted azole diones to selectively sensitize cancer cells to DNA damaging reagents, treatments and/or other types of anti-cancer reagents.
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Page/Page column 86
(2008/12/08)
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- The "off-shore" construction of optionally substituted 4-trifluoromethyl-2-quinolinones
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Treatment of ortho-lithiated tert-butyl N-arylcarbamates (i.e., BOC-protected anilines) with N-(trifluoroacetyl)piperidine provides 2-(N-BOC-amino)aryl trifluoromethyl ketones which, upon consecutive reaction with an α-alkoxycarbonyl-substituted phosphoru
- Leroux, Frederic,Lefebvre, Olivier,Schlosser, Manfred
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p. 3147 - 3151
(2007/10/03)
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- An Improved Access to 4-Trifluoromethyl-2(1H)-quinolinones: The "Watering Protocol"
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Condensation of anilines with ethyl 4,4,4-trifluoroacetoacetate (7) to afford the corresponding 4,4,4-trifluoro-3-oxobutaneanilides (10), precursors to 4-(trifluoromethyl)-2-quinolinones (11), can be favored and the competing condensation to produce the e
- Marull, Marc,Lefebvre, Olivier,Schlosser, Manfred
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- 4-(Trifluoromethyl)quinoline derivatives
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Under carefully controlled conditions, ethyl 4,4,4-trifluoroacetoacetate (ethyl 4,4,4-trifluoro-3-oxobutanoate) can be condensed with anilines and subsequently cyclized to give 4-trifluoromethyl-2-quinolinones 1 although only in poor yield. Heating these products with phosphoryl tribromide affords 2-bromo-4-(trifluoromethyl)quinolines 2 which can be converted into 4-(trifluoromethyl)quinolines 3 by reduction, 4-trifluoromethyl-2-quinolinecarboxylic acids 4 by permutational halogen/metal exchange followed by carboxylation, and 2-bromo-4-trifluoromethyl-3-quinolinecarboxylic acids 5 by consecutive treatment with lithium diisopropylamide and dry ice. Debromination of acids 5 makes 4-trifluoromethyl-3-quinolinecarboxylic acids 6 available. As at any time 2-trifluoromethyl-4-quinolinones 9 may form instead of the expected isomers 1, the structures have to be assigned on the basis of unequivocal NMR spectral criteria. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- Lefebvre, Olivier,Marull, Marc,Schlosser, Manfred
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p. 2115 - 2121
(2007/10/03)
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- Facile and regioselective synthesis of 4-fluoroalkyl-2-quinolinol
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4-Fluoroalkyl-2-quinolinols were regioselectively synthesized in moderate to high yields by acid-assisted intramolecular ring-closure reaction of the corresponding N-aryl-3-oxa-polyfluoroalkanamides prepared from 2,2-dihydropolyfluoroalkanoic acids in two
- Liu, Jin-Tao,Lü, He-Jun
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p. 207 - 212
(2007/10/03)
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