59824-69-0Relevant academic research and scientific papers
SUBSTITUTED AMINOQUINOLONES AS DGKALPHA INHIBITORS FOR IMMUNE ACTIVATION
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Page/Page column 259, (2021/06/04)
The present invention covers aminoquinolone compounds of general formula (I), in which R1, R2, R3, R4, R5, R6, R7, R8 and n are as defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment and/or prophylaxis of diseases, in particular of diacylglycerol kinase alpha regulated disorders, as a sole agent or in combination with other active ingredients.
Palladium-Catalyzed Multistep Tandem Carbonylation/N-Dealkylation/Carbonylation Reaction: Access to Isatoic Anhydrides
Wang, Shoucai,Li, Xuan,Zang, Jiawang,Liu, Meichen,Zhang, Siyu,Jiang, Guangbin,Ji, Fanghua
, p. 2672 - 2679 (2020/02/04)
A novel and efficient synthesis of isatoic anhydride derivatives was developed via palladium-catalyzed multistep tandem carbonylation/N-dealkylation/carbonylation reaction with alkyl as the leaving group and tertiary anilines as nitrogen nucleophiles. This approach features good functional group compatibility and readily available starting materials. Furthermore, it provided a convenient approach for the synthesis of biologically and medicinally useful evodiamine.
Carbene-Catalyzed Enantioselective Decarboxylative Annulations to Access Dihydrobenzoxazinones and Quinolones
Lee, Ansoo,Zhu, Joshua L.,Feoktistova, Taisiia,Brueckner, Alexander C.,Cheong, Paul H.-Y.,Scheidt, Karl A.
supporting information, p. 5941 - 5945 (2019/04/03)
A direct decarboxylative strategy for the generation of aza-o-quinone methides (aza-o-QMs) by N-heterocyclic carbene (NHC) catalysis has been discovered and explored. This process requires no stoichiometric additives in contrast with current approaches. Aza-o-QMs react with trifluoromethyl ketones through a formal [4+2] manifold to access highly enantioenriched dihydrobenzoxazin-4-one products, which can be converted to dihydroquinolones through an interesting stereoretentive aza-Petasis–Ferrier rearrangement sequence. Complementary dispersion-corrected density functional theory (DFT) studies provided an accurate prediction of the reaction enantioselectivity and lend further insight to the origins of stereocontrol. Additionally, a computed potential energy surface around the major transition structure suggests a concerted asynchronous mechanism for the formal annulation.
PHARMACEUTICAL COMPOSITION AND APPLICATION REPLACING QUINOLONE DERIVATIVE, PHARMACEUTICAL ACCEPTABLE SALT, OR STEREOISOMER
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Paragraph 0050; 0052, (2018/07/06)
Provided are a substituted quinolone derivative as shown by formula (I), or a pharmaceutically acceptable salt and a prodrug molecule thereof, and a pharmaceutical composition thereof, as well as the use of same in preparing drugs for the prevention and treatment of a tumor. The quinolone derivative, salt, prodrug molecule, and pharmaceutical composition thereof can be used as a protein kinase inhibitor, which is effective in inhibiting the activity of AXL protein kinase, and is capable of inhibiting the proliferation, migration and invasion of various tumor cells; and can be used in the preparation of anti-tumor drugs, especially drugs for treating hyperproliferative diseases such as a tumor in human beings and other mammals.
Synthesis method of constructing isatoic anhydride and isatoic anhydride derivative by one step by utilizing carbonylation reaction
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Paragraph 0068; 0069, (2017/11/16)
The invention relates to a method of constructing isatoic anhydride and an isatoic anhydride derivative by one step by utilizing a carbonylation reaction. The method comprises the steps of adding N,N-dialkyl arylamine, a metal palladium catalyst and copper salt as an oxidant and a solvent to a reaction vessel, sleeving a balloon filled with carbon monoxide and oxygen on a reactor, performing a stirring reaction for 1-10h at 40-150 DEG C, performing cooling to a room temperature after reaction completion, dismounting the balloon, filtering a reaction liquid, performing reduced pressure evaporation to remove the solvent to obtain a crude product, and performing column chromatography purification to obtain isatoic anhydride and the isatoic anhydride derivative. The synthesis method of constructing isatoic anhydride and the isatoic anhydride derivative by the one step by utilizing the carbonylation reaction has the characteristics that operation is concise, raw materials are easy to obtain, the functional group tolerance is good, and a yield is excellent; and the method has an important research value on synthesis and preparation of isatoic anhydride and the isatoic anhydride derivative.
4-Oxo-1,4-dihydroquinoline-3-carboxamide Derivatives as New Axl Kinase Inhibitors
Tan, Li,Zhang, Zhang,Gao, Donglin,Luo, Jinfeng,Tu, Zheng-Chao,Li, Zhengqiu,Peng, Lijie,Ren, Xiaomei,Ding, Ke
, p. 6807 - 6825 (2016/08/05)
Axl is a new potential target for anticancer drug discovery. A series of 4-oxo-1,4-dihydroquinoline-3-carboxamides were designed and synthesized as highly potent Axl kinase inhibitors. One of the most promising compounds, 9im, tightly bound with Axl prote
Palladium-catalyzed regioselective carbonylation of C-H bonds of N -alkyl anilines for synthesis of isatoic anhydrides
Guan, Zheng-Hui,Chen, Ming,Ren, Zhi-Hui
supporting information, p. 17490 - 17493,4 (2020/09/16)
A Pd-catalyzed regioselective C-H bond carbonylation of N-alkyl anilines for the synthesis of isatoic anhydrides has been developed. The key Pd-catalyst intermediate has been isolated and characterized. This novel Pd-catalyzed carbonylation reaction tolerates a wide range of functional groups and is a reliable method for the rapid elaboration of readily available N-alkyl anilines into a variety of substituted isatoic anhydrides under mild conditions.
1,3-dipolar cycloaddition-decarboxylation reactions of an azomethine ylide with isatoic anhydrides: Formation of novel benzodiazepinones
D'Souza, Asha M.,Spiccia, Nadia,Basutto, Jose,Jokisz, Pawel,Wong, Leon S.-M.,Meyer, Adam G.,Holmes, Andrew B.,White, Jonathan M.,Ryan, John H.
supporting information; experimental part, p. 486 - 489 (2011/03/23)
A nonstabilized azomethine ylide reacts with a wide range of substituted isatoic anhydrides to afford novel 1,3-benzodiazepin-5-one derivatives, which are generally isolated in high yield. The transformations involve 1,3-dipolar cycloaddition reactions of the ylide with the anhydrides to give transient, and in a representative case spectroscopically observable, oxazolidine intermediates that undergo ring-opening-decarboxylation-ringclosing reaction cascades to yield the 1,3-benzodiazepin-5-one products.
INHIBITORS OF MACROPHAGE MIGRATION INHIBITORY FACTOR AND METHODS FOR IDENTIFYING THE SAME
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Page 98, (2010/02/08)
Inhibitors of MIF are provided which have utility in the treatment of a variety of disorders, including the treatment of pathological conditions associated with MIF activity. The inhibitors of MIF have the following structures (Ia), (Ib) including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof, wherein n, R1, R2, R3, R4, X, and Z are as defined herein. Compositions containing an inhibitor of MIF in combination with a pharmaceutically acceptable carrier are also provided, as well as methods for use of the same.
Antihypertensive 3-tetrazoyl-4-quinolones
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, (2008/06/13)
Novel quinolones of formula I STR1 and pharmaceutically acceptable acid addition salts thereof in which the dotted line between positions 2 and 3 of the quinolone ring represents an optional bond, R is hydrogen, 1-methyl or 2-lower alkyl; R1 is lower alkyl; R2 is hydrogen, halo, lower alkyl, lower alkoxy, trifluoromethyl, cyano, difluoromethoxy, methylsulphinyl, phenylsulphinyl or the group --NR4 R5 or the N-oxide thereof wherein R4 and R5, which may be the same or different, are lower alkyl or, together with the nitrogen atom to which they are attached form a pyrrolidino, piperidino or morpholino radical; and R3 is hydrogen, fluoro, lower alkyl or lower alkoxy provided that, when R3 is lower alkoxy, R2 is other than lower alkoxy have utility as antihypertensive agents. Processes for preparing the quinolones and pharmaceutical compositions containing them are disclosed.
