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Synthesis and Study of New Quinolineaminoethanols as Anti-Bacterial Drugs

1
AGIR, EA 4294, UFR of Pharmacy, Jules Verne University of Picardie, 80037 Amiens, France
2
Department of Bacteriology, Amiens University Hospital, 80054 Amiens, France
3
Respiratory and Intensive Care Unit, University Hospital Amiens, 80054 Amiens, France
*
Authors to whom correspondence should be addressed.
Pharmaceuticals 2019, 12(2), 91; https://doi.org/10.3390/ph12020091
Received: 29 May 2019 / Revised: 12 June 2019 / Accepted: 14 June 2019 / Published: 18 June 2019
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Abstract

The lack of antibiotics with a novel mode of action associated with the spread of drug resistant bacteria make the fight against infectious diseases particularly challenging. A quinoline core is found in several anti-infectious drugs, such as mefloquine and bedaquiline. Two main objectives were set in this work. Firstly, we evaluated the anti-mycobacterial properties of the previous quinolines 3, which have been identified as good candidates against ESKAPEE (Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, Enterobacter spp. and Escherichia coli) bacteria. Secondly, a new series 4 was designed and assessed against the same bacteria strains, taking the pair of enantiomers 3m/3n as the lead. More than twenty compounds 4 were prepared through a five-step asymmetric synthesis with good enantiomeric excesses (>90%). Interestingly, all compounds of series 3 were efficient on M. avium with MIC = 2–16 µg/mL, while series 4 was less active. Both series 3 and 4 were generally more active than mefloquine against the ESKAPEE bacteria. The quinolines 4 were either active against Gram-positive bacteria (MIC ≤ 4 µg/mL for 4c4h and 4k/4l) or E. coli (MIC = 32–64 µg/mL for 4q4v) according to the global lipophilicity of these compounds. View Full-Text
Keywords: Quinoline; tuberculosis; nosocomial infections; ESKAPEE bacteria; mycobacterium Quinoline; tuberculosis; nosocomial infections; ESKAPEE bacteria; mycobacterium
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Laumaillé, P.; Dassonville-Klimpt, A.; Peltier, F.; Mullié, C.; Andréjak, C.; Da-Nascimento, S.; Castelain, S.; Sonnet, P. Synthesis and Study of New Quinolineaminoethanols as Anti-Bacterial Drugs. Pharmaceuticals 2019, 12, 91.

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