1. Synthesis of fluorinated carbazoles via C-H arylation catalyzed by Pd/Cu bimetal system and their antibacterial activities.
- Author
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Kong X, Zhang H, Cao C, Zhou S, Pang G, and Shi Y
- Subjects
- Anti-Bacterial Agents chemistry, Bacillus subtilis drug effects, Carbazoles chemistry, Catalysis, Dose-Response Relationship, Drug, Escherichia coli drug effects, Methicillin-Resistant Staphylococcus aureus drug effects, Microbial Sensitivity Tests, Molecular Structure, Organometallic Compounds chemistry, Staphylococcus aureus drug effects, Structure-Activity Relationship, Anti-Bacterial Agents chemical synthesis, Anti-Bacterial Agents pharmacology, Carbazoles chemical synthesis, Carbazoles pharmacology, Copper chemistry, Fluorine chemistry, Palladium chemistry
- Abstract
An effective intramolecular C-H arylation reaction catalyzed by a bimetallic catalytic system Pd(OAc)2/CuI for the synthesis of fluorine-substituted carbazoles from corresponding N-phenyl-2-haloaniline derivatives under ligand free conditions is demonstrated. The established method is effective for both N-phenyl-2-bromoaniline and N-phenyl-2-chloroaniline, and requires the low loading of Pd(OAc)2 (0.5 mol%). A series of new fluorinated carbazoles were synthesized in excellent yields using the protocol (>83%, 19 examples) and were fully characterized by (1)H, (13)C and (19)F NMR spectral data, HRMS and elemental analysis. All compounds were evaluated for their antibacterial activities against four bacteria (Bacillus subtilis, Staphylococcus aureus, Escherichia coli and methicillin-resistant S. aureus with resistance to gentamicin) by serial dilution technique. All tested compounds showed antibacterial activity against three test strains (S. aureus, B. subtilis and MRSA), and most of these compounds displayed pronounced antimicrobial activities against these three strains with low MIC values ranging from 0.39 to 6.25 μg/mL. Among them, compounds 7 and 14 exhibited potent inhibitory activity better than reference drugs meropenem and streptomycin. Three compounds (2, 4 and 5) showed antibacterial activity against E. coli. with MIC values from 12.5 to 25 μg/mL., (Copyright © 2016 Elsevier Ltd. All rights reserved.)
- Published
- 2016
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