- A Selective and Orally Bioavailable Quinoline-6-Carbonitrile-Based Inhibitor of CDK8/19 Mediator Kinase with Tumor-Enriched Pharmacokinetics
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Senexins are potent and selective quinazoline inhibitors of CDK8/19 Mediator kinases. To improve their potency and metabolic stability, quinoline-based derivatives were designed through a structure-guided strategy based on the simulated drug–target dockin
- Zhang, Li,Cheng, Chen,Li, Jing,Wang, Lili,Chumanevich, Alexander A.,Porter, Donald C.,Mindich, Aleksei,Gorbunova, Svetlana,Roninson, Igor B.,Chen, Mengqian,McInnes, Campbell
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p. 3420 - 3433
(2022/02/16)
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- Method for synthesizing organic intermediate compound
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The invention provides a method for synthesizing an organic intermediate compound. The method comprises the step of synthesizing a compound of formula (I) by taking a compound of formula (II) as a starting material, wherein R is selected from phenyl subst
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Paragraph 0042-0044
(2019/12/25)
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- TMSI-Promoted vinylogous michael addition of siloxyfuran to 2-substituted chromones: A general approach for the total synthesis of chromanone lactone natural products
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A concise and facile synthetic protocol for the construction of the 2-γ-lactone chromanone skeleton has been achieved through a TMSI-promoted diastereoselective vinylogous Michael addition of siloxyfuran to 2-substituted chromones. The applicability of this method is demonstrated through the rapid access to the total syntheses of (±)-microdiplodiasone, (±)-lachnone C, and (±)-gonytolides C and G.
- Liu, Jie,Li, Zhanchao,Tong, Pei,Xie, Zhixiang,Zhang, Yuan,Li, Ying
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supporting information
p. 1632 - 1643
(2015/02/19)
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- A concise synthesis of indoloquinoline skeletons applying two consecutive Pd-catalyzed reactions
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The indoloquinoline alkaloids cryptolepine (1), neocryptolepine (2), isocryptolepine (3), and isoneocryptolepine (4) are important tools in traditional medicine. Now, their precursors 1a-4a were synthesized in two steps starting from the corresponding bromo-iodoquinolines. Our strategy is based on palladium-catalyzed reactions, applying regioselective Buchwald-Hartwig amination on 2,3- and 3,4-dihaloquinolines followed by an intramolecular Heck-type reaction. Both steps were carried out under microwave irradiation.
- Bogányi, Borbála,Kámán, Judit
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p. 9512 - 9519
(2013/10/08)
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- A novel ionic liquid mediated synthesis of 4(1H)-quinolones, 5H-thiazolo[3,2-a]pyrimidin-5-one and 4H-pyrimido[2,1-b]benzothiazol-4-ones
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A new, convenient, environmentally benign two-step synthesis of 4(1H)-quinolones, 5H-thiazolo[3,2-a]pyrimidin-5-one and 4H-pyrimido[2,1-b] benzothiazol-4-ones have been developed by first condensing substituted arylamine/2-aminothiazole/2-aminobenzenethia
- Yadav, Ashok K.,Sharma, Gopi Ram,Dhakad, Pankaj,Yadav, Tripti
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experimental part
p. 859 - 862
(2012/03/08)
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- Highly efficient thermal cyclization reactions of alkylidene esters in continuous flow to give aromatic/heteroaromatic derivatives
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Intramolecular thermal cyclization and benzannulation reactions of the Gould-Jacobs and Conrad-Limpach types were performed in a designed continuous flow reactor system at temperatures in the range of 300-360°C and under high pressure conditions (100-160 bar) with very short residence times (0.45-4.5 min) in tetrahydrofuran as a low-boiling point solvent. Substituted heteroaromatic compounds including pyridopyrimidinones and hydroxyquinolines were synthesized in moderate to high yields. Application of the reaction conditions also allows the synthesis of naphthol and biphenyl derivatives. The procedure involves an easy work-up and the non-batchwise preparative synthesis method is suitable for automation.
- Lengyel, László,Nagy, Tibor Zs.,Sipos, Gellért,Jones, Richard,Dormán, Gy?rgy,ürge, László,Darvas, Ferenc
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experimental part
p. 738 - 743
(2012/03/08)
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- Regioselective synthesis of quinolin-4-ones by pyrolysis of anilinomethylene derivatives of Meldrum's acid
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Electron-rich and electron-deficient anilinomethylene derivatives of Meldrum's acid cyclize equally efficiently to quinolin-4-ones via imidoylketene intermediates under flash vacuum pyrolysis (FVP) conditions. Georg Thieme Verlag Stuttgart.
- Hill, Lawrence,Imam, S. Haider,McNab, Hamish,O'Neill, William J.
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experimental part
p. 1847 - 1851
(2009/12/05)
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- Structure-activity relationship, kinetic mechanism, and selectivity for a new class of ubiquitin C-terminal hydrolase-L1 (UCH-L1) inhibitors
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3-Amino-2-keto-7H-thieno[2,3-b]pyridin-6-one derivatives were discovered as moderately potent inhibitors of ubiquitin C-terminal hydrolase-L1 (UCH-L1) utilizing an assay that measures hydrolysis of the fluorogenic substrate Ub-AMC. SAR studies revealed that both the carboxylate at the 5-position and the 6-pyridone ring were critical for inhibitory activity. Furthermore, activity was dependent on the nature of the ketone substituent at the 2-position, with 4-Me-Ph and 2-naphthyl being best. Kinetic mechanism studies revealed that these compounds were uncompetitive inhibitors of UCH-L1, binding only to the Michaelis-complex and not to free enzyme. The active compounds were selective for UCH-L1, exhibiting neither inhibition of other cysteine hydrolases (e.g., UCH-L3, papain, isopeptidase T, caspase-3, and tissue transglutaminase) nor cytotoxicity in N2A cells.
- Mermerian, Ara H.,Case, April,Stein, Ross L.,Cuny, Gregory D.
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p. 3729 - 3732
(2008/02/10)
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- Gas-phase pyrolysis in organic synthesis: Rapid green synthesis of 4-quinolinones
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Gas-phase pyrolysis of aminomethylene Meldrum's acid derivatives gave quinolinones and/or amines depending on the nature of arylamino moiety. Effect of substituent on reaction rate and nature of pyrolysis products supports the suggested intramolecular nucleophilic substitution reaction via initially formed keteneamine intermediate. Georg Thieme Verlag Stuttgart.
- Al-Awadi, Nouria A.,Abdelhamid, Ismail Abdelshafy,Al-Etaibi, Alya M.,Elnagdi, Mohamed Hilmy
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p. 2205 - 2208
(2008/02/10)
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- Anilinomethylidene derivatives of cyclic 1,3-dicarbonyl compounds in the synthesis of new sulfur-containing pyridines and quinolines
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Simple methods for the synthesis of previously unknown sulfur-containing pyridin-2-ones and 5,6,7,8-tetrahydroquinolines from cyanothioacetamide and anilinomethylidene derivatives of cyclic 1,3-dicarbonyl compounds were developed. Structures and chemical transformations of compounds obtained were studied.
- Dotsenko,Krivokolysko,Chernega,Litvinov
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p. 1556 - 1561
(2007/10/03)
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- Exotic amino acids. 8. Synthesis of monomethyl esters of N-aryl-aminomethylenemalonic acids
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N-Arylaminomethyleneisopropylidenemalonates, obtained from ethoxymethyleneisopropylidenemalonate and aromatic amines, underwent methanolysis to form monomethyl esters of N-arylaminomethylenemalonic acids. The conditions of their formation and their yields depend on the nature and positions of the substituents in the aromatic ring of the initial amine.
- Zicane,Ravina,Tetere,Rijkure,Petrova,Kalejs
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p. 840 - 845
(2007/10/03)
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- 3-Hydroxypyrroles and 1H-Pyrrol-3(2H)-ones. Part 2. Scope and Limitations of the Synthesis of Pyrrol-3-ones by Pyrolysis of Aminomethylene Meldrum's Acid Derivatives.
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Flash vacuum pyrolysis of N,N-disubstituted aminomethylene Meldrum's acid derivatives provides a route to 4,5-unsubstituted 1H-pyrrol-3(2H)-ones by a hydrogen-transfer-cyclisation sequence.Alkyl and aryl 1-substituted, 1,2-disubstituted, and 1,2,2-trisubstituted pyrrolones can be obtained.In competitive cases, there is little selectivity between hydrogen transfer from primary, secondary, or tertiary sites, although benzyl hydrogen atoms proved particularly reactive, giving a general synthesis of 2-phenyl-1H-pyrrol-3(2H)-ones.
- McNab, Hamish,Monahan, Lilian C.
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p. 863 - 868
(2007/10/02)
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- SYNTHESIS OF 4(1H)-QUINOLONES BY THERMOLYSIS OF ARYLAMINOMETHYLENE MELDRUM'S ACID DERIVATIVES
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A series of 4(1H)-quinolones were obtained from Meldrum's acid and arylamines in two steps.
- Cassis, Raul,Tapia, Ricardo,Valderrama, Jaime A.
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p. 125 - 134
(2007/10/02)
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- Introduction of Oxygen Functions into the α-Position of β-Diketones, 4: "Hydroxy- and Oxo-Meldrum's Acids"
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Synthesis and properties of 5-hydroxy-, 5-acyloxy-, 5-oxo- and 5,5-dihydroxy-2,2-dialkyl-1,3-dioxane-4,6-diones (6, 5/9, 7, 10) are described.
- Bouillon, Guenther,Schank, Kurt
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p. 2630 - 2635
(2007/10/02)
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