- Fluorine-containing 2,3-diaryl quinolines as potent inhibitors of methicillin and vancomycin-resistant Staphylococcus aureus: Synthesis, antibacterial activity and molecular docking studies
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Drug resistant bacteria pose a major health concern and affect a large section of global population. Antibacterial drug discovery has stagnated owing to multiple factors including unattractive returns for major pharmaceutical companies. Thus, discovery of effective antibacterial drugs against drug-resistant bacteria is an urgent unmet need affecting healthcare systems globally. In this study, fluorine-containing 2,3-diarylquinolines (4a-l) and non-fluorinated analog 4m were synthesized utilizing environmentally benign chemistry of arenediazonium salts and arynes for regioselective installation of aryl groups at C-2 and C-3 positions, respectively. In vitro antibacterial evaluation against various Gram-negative and Gram-positive bacteria revealed inhibitory activity of majority of these compounds against Gram-positive S. aureus ATCC 29213. Compounds 4e, 4i, 4j and 4l were most potent inhibitors with MIC values of 10.95?24.0 μM. None of the compounds inhibited Gram-negative bacteria. 4e, 4i and 4l also displayed low levels of cytotoxicity against Vero cells, therefore, offering high safety profiles. Importantly, 4e, 4i and 4l exhibited equipotent inhibition of Methicillin and Vancomycin-resistant S. aureus, rendering them potential hits for further development. Molecular docking studies with topoisomerase II DNA gyrase demonstrated significant interactions of these inhibitors with target protein, which provided valuable insights into their potent antibacterial activity.
- Akhir, Abdul,Banerjee, Shaibal,Chopra, Sidharth,Janeoo, Shashi,Kaul, Grace,Kaur, Harminder,Kumar, Rakesh,Kumar, Varinder,Reenu
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- Visible-light-promoted c2 selective arylation of quinoline and pyridine n-oxides with diaryliodonium tetrafluoroborate
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A protocol of visible-light-promoted C2 selective arylation of quinoline and pyridine N-oxides, with diaryliodonium tetrafluoroborate as an arylation reagent, using eosin Y as a photocatalyst for the construction of N-heterobiaryls was presented. This met
- Li, Dazhi,Liang, Ce,Jiang, Zaixing,Zhang, Junzheng,Zhuo, Wang-Tao,Zou, Fan-Yue,Wang, Wan-Peng,Gao, Guo-Lin,Song, Jinzhu
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p. 2733 - 2742
(2020/03/11)
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- Preparation method of 2- aryl substituted quinoline nitrogen oxide compound
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The preparation method 2 - of, aryl-substituted quinoline nitrogen oxide is 2 - The method, according to the present invention provides,aryl-substituted quinoline nitrogen oxide compound, in a nitrogen atmosphere at room temperature, The method for prepar
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Paragraph 0134-0145
(2020/03/16)
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- Combining C-H functionalisation and flow photochemical heterocyclic metamorphosis (FP-HM) for the synthesis of benzo[1,3]oxazepines
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C-H Activation/functionalisation and Flow Photochemical Heterocyclic Metamorphosis (FP-HM) have been combined to synthesize a library of benzo [1,3]oxazepines, a rarely described heterocyclic family. This combined protocol allows a range of arylated products to be made from simple starting materials, and the cheap flow photochemical system has proven effective for rapid synthesis of gram-quantities of benzo [1,3]oxazepines.
- Babra, Jasraj S.,Russell, Andrew T.,Smith, Christopher D.,Zhang, Yuxiong
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p. 5351 - 5357
(2018/05/31)
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- KMnO4-mediated direct selective radical cross-coupling: An effective strategy for C2 arylation of quinoline N-oxide with arylboronic acids
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Direct C[sbnd]H functionalization of quinoline N-oxides with arylboronic acids is achieved using KMnO4 as the sole and efficient oxidative system. This method provides an efficient protocol to construct regioselectively 2-arylquinoline N-oxides
- Yuan, Jin-Wei,Qu, Ling-Bo
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supporting information
p. 981 - 985
(2017/05/22)
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- KMnO4-mediated direct C2-selective C?H arylation of quinoline N-oxides with aromatic hydrazines
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An efficient protocol for the synthesis of 2-arylquinoline N-oxides has been developed via KMnO4-mediated cross-coupling reaction of quinoline N-oxides with aromatic hydrazines in moderated to good yields. The reactions proceeded efficiently over a broad range of substrates with excellent regioselectivity and functional group tolerance.
- Yuan, Jin-Wei,Li, Wei-Jie,Xiao, Yong-Mei
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p. 179 - 186
(2016/12/23)
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- Cu(OAc)2-catalyzed direct radical C2 arylation of quinoline N-oxide with arylamines
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A Cu(OAc)2-catalyzed synthesis of 2-arylquinoline N-oxides with easily available arylamines is described. The main features of this reaction are mild reaction conditions, high functional-group tolerance, excellent regioselectivity, and good to excellent yields. This procedure is mild, operationally simple, and constitutes a greener approach to the arylation of quinoline N-oxides.
- Yuan, Jin-Wei,Liu, Shuai-Nan,Qu, Ling-Bo
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p. 2267 - 2275
(2017/03/24)
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- Direct arylations of electron-deficient (hetero)arenes with aryl or alkenyl tosylates and mesylates
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A palladium catalyst derived from the ligand X-Phos enabled generally applicable direct arylations of electron-deficient heteroarenes and arenes with aryl and alkenyl tosylates or mesylates.
- Ackermann, Lutz,Fenner, Sabine
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supporting information; experimental part
p. 430 - 432
(2011/02/28)
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