26707-52-8Relevant articles and documents
Synthesis and biological activity of 2-[2-(7-chloroquinolin-4-ylthio)-4-methylthiazol-5-yl]-N-phenylacetamide derivatives as antimalarial and cytotoxic agents
Rámirez, Hegira,Rodrigues, Juan R,Mijares, Michael R,De Sanctis, Juan B,Charris, Jaime E
, p. 305 - 314 (2020)
A novel series of 2-[2-(7-chloroquinolin-4-ylthio)-4-methylthiazol-5-yl]-N-phenylacetamide derivatives is synthesized via substitution with 2-mercapto-4-methyl-5-thiazoleacetic acid at position 4 of 4,7-dichloroquinoline to obtain an intermediate acetic acid derivative. The chemical behavior of these reactants was investigated using different reaction conditions to optimize the nucleophilic substitution at position 4. The final compounds are prepared using a modified version of the Steglich esterification reaction between the acetic acid intermediate 3 and different anilines. The structures are confirmed by infrared, 1H, 13C, distortionless enhancement by polarization transfer 135°, Correlated Spectroscopy, heteronuclear correlation spectroscopy and (Long range HETCOR using three BIRD pulses) FLOCK-NMR spectral studies, and by elemental analysis. The synthesized compounds are tested in vitro and in vivo for their potential antimalarial and anticancer activities, with derivative 11 being the most promising candidate.
Studies toward the Synthesis of Lepadiformine A
Tsukanov, Sergey V.,Marks, Lucas R.,Comins, Daniel L.
, p. 10433 - 10443 (2016)
Herein is described an original approach to access a tricyclic framework of the lepadiformine-type alkaloids. A Grignard/N-acylpyridinium salt reaction of a 4-methoxytetrahydroquinoline is the key carbon-carbon bond-forming step that was used to establish the desired absolute stereochemistry at the C2 position of the target alkaloid. The synthesis features an allylation reaction with an N-acyliminium ion to set the C10 quaternary stereocenter, a mild dissolving-metal cleavage of hindered phenyl carbamates, and an aminoiodocyclization to form the pyrrolidine ring. While this route does not provide the correct C10 stereochemistry, it showcases an efficient method to build analogues with the ring system of this class of alkaloids in 11 steps overall.
Design and synthesis of 4(1H)-quinolone derivatives as autophagy inducing agents by targeting ATG5 protein
Jia, Yifan,Yu, Difei,Huang, Qiuhua,Zhang, Xiaodong,Qiu, Liqin,Cao, Rihui,Du, Runlei,Liu, Wenbin
, p. 884 - 890 (2020/07/10)
Background: Quinolines have been characterized as a class of potential antitumor agents, and a large number of natural and synthetic quinolines acting as antitumor agents were reported. Methods: A series of 7-chloro-4(1H)-quinolone derivatives were synthesized. The antiproliferative effect of these compounds was evaluated by MTT assay against five human tumor cell lines. The mechanism of action of the selected compound 7h was also investigated. Results and Discussion: Most of the compounds had more potent antiproliferative activities than the lead compound 7-chloro-4(1H)-quinolone 6b. Compound 7h was found to be the most potent antiproliferative agent against human tumor cell lines. Further investigation demonstrated that compound 7h triggered ATG5-dependent autophagy of colorectal cancer cells by promoting the functions of LC3 proteins. Conclusion: These results were useful for designing and discovering more potent novel antitumor agents endowed with better pharmacological profiles.
PYRAZOLE DERIVATIVES AS MALT1 INHIBITORS
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Paragraph 1255; 1256, (2018/07/05)
Disclosed are compounds, compositions and methods for treating of diseases, syndromes, conditions, and disorders that are affected by the modulation of MALT1. Such compounds are represented by Formula (I) as follows: wherein R1, R2, R3, R4, R5, R6, R5, G1, and G2 are defined herein.
For antibacterial chlorine oxygen kui derivatives
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, (2017/08/29)
The invention relates to an oxo-quinoline derivative with activity of resisting bacterial infection relevant diseases such as helicobacter pylori (Hp) infection disease. The invention specifically relates to a compound as shown in formula I in the specification, and a pharmaceutically acceptable salt, solvate or prodrug thereof, wherein R is selected from hydrogen, -C alkyl, -C alkenyl, -C alkynyl, or -C alkyl-phenyl, and the alkyl, alkenyl, alkynyl and phenyl can be randomly substituted by halogen, nitro, cyan, hydroxyl, -C alkoxy and phenyl; R is selected from hydrogen, -CONHR and -COOR, R and R are independently selected from -C alkyl and -C alkyl amino, and the amino is randomly substituted by one to two -C alkyls; R is selected from halogen, -C alkoxy, morpholinyl or piperazinyl.
With anti-tumor activity of chlorine oxygen kui derivatives
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Paragraph 0301; 0307; 0308, (2017/12/28)
The invention relates to a chloroxoquinoline derivatives with anti-tumor activity and specifically relates to compounds of a formula I as shown in the specification and pharmaceutically acceptable salts, solvates and prodrugs thereof, wherein R1 is selected from hydrogen, -C1-6 alkyl, -C2-6 alkenyl, -C2-6 alkynyl and -C1-6 alkyl-phenyl, and the alkyl, the alkenyl, the alkynyl and the phenyl can be optionally substituted by halogens, nitryl, cyan, hydroxyl, -C1-6 alkoxy and phenyl; R3 is selected from hydrogen, -CONHR31 and -COOR32, the R31 and the R32 are independently selected from -C1-6 alkyl and -C1-6 alkylamino, respectively, and the amino can be optionally substituted by 1 to 2 -C1-6 alkyls; R7 is selected from halogens, -C1-6 alkoxy, morpholinyl and piperazine; the formula I is as shown in the specification.
A new and potent class of quinoline derivatives against cancer
Bispo, Marcelle De L. F.,De Alcantara, Camila C.,De Moraes, Manoel O.,Do ó Pessoa, Cláudia,Rodrigues, Felipe A. R.,Kaiser, Carlos R.,Wardell, Solange M. S. V.,Wardell, James L.,De Souza, Marcus V. N.
, p. 2041 - 2052 (2015/11/24)
A new class of 4-quinolinylhydrazone derivatives has been synthesized and evaluated for their cytotoxic potential against three cancer cell lines using the MTT assay. Compounds displaying more than 90 % of growth inhibition were evaluated for in vitro anticancer activities against four human cancer cell lines. The results were expressed as the concentrations that induce 50 % inhibition of cell growth (IC50) in μg/cm3. These compounds exhibited good cytotoxic activity against at least three cancer cell lines, with IC50 values between 0.314 and 4.65 μg/cm3. These derivatives are useful starting points for further study for new anticancer drugs and confirm the potential of quinoline derivatives as lead compounds in anticancer drug discovery. Graphical Abstract: [Figure not available: see fulltext.]
Synthetic and mechanistic aspects of the regioselective base-mediated reaction of perfluoroalkyl- and perfluoroarylsilanes with heterocyclic N-oxides
Stephens, David E.,Chavez, Gabriel,Valdes, Martin,Dovalina, Monica,Arman, Hadi D.,Larionov, Oleg V.
supporting information, p. 6190 - 6199 (2014/08/05)
The scope and mechanistic implications of the direct transformation of heterocyclic N-oxides to 2-trifluoromethyl-, and related perfluoroalkyl- and perfluoroaryl-substituted N-heterocycles has been studied. The reaction is effected by perfluoroalkyl- and perfluorophenyltrimethylsilane in the presence of strong base. In situ displacement of the para-fluoro substituent in the pentafluorophenyl ring and the methoxy group in 8-methoxyquinolines with additional nucleophiles allows for further site-selective refunctionalization of the N-heterocyclic products. This journal is the Partner Organisations 2014.
Direct, catalytic, and regioselective synthesis of 2-alkyl-, aryl-, and alkenyl-substituted N -Heterocycles from n -oxides
Larionov, Oleg V.,Stephens, David,Mfuh, Adelphe,Chavez, Gabriel
supporting information, p. 864 - 867 (2014/03/21)
A one-step transformation of heterocyclic N-oxides to 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles is described. The success of this broad-scope methodology hinges on the combination of copper catalysis and activation by lithium fluoride or magnesium chloride. The utility of this method for the late-stage modification of complex N-heterocycles is exemplified by facile syntheses of new structural analogues of several antimalarial, antimicrobial, and fungicidal agents.
Asymmetric synthesis of C2-symmetric vicinal diamines via reductive dimerization of N-acylpyridinium and related salts
Bharathi, Pandi,Comins, Daniel L.
, p. 221 - 223 (2008/09/18)
(Chemical Equation Presented) A new route to C2-symmetric diamines via an asymmetric reductive dimerization of 1-acylpyridinium salts and their benzo derivatives is described. This method is practical as the starting heterocycles and chiral aux
