Synthesis and Study of New Quinolineaminoethanols as Anti-Bacterial Drugs

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...

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Veröffentlicht in:Pharmaceuticals Jg. 12; H. 2; S. 91
Hauptverfasser: Laumaillé, Pierre, Dassonville-Klimpt, Alexandra, Peltier, François, Mullié, Catherine, Andréjak, Claire, Da-Nascimento, Sophie, Castelain, Sandrine, Sonnet, Pascal
Format: Journal Article
Sprache:Englisch
Veröffentlicht: Switzerland MDPI AG 18.06.2019
MDPI
Schriftenreihe:Selected Papers from the 4th International Electronic Conference on Medicinal Chemistry
Schlagworte:
[CHIM]Chemical Sciences
[SDV]Life Sciences [q-bio]
Antibiotics
Antimicrobial agents
Bacteria
Chemical Sciences
Drugs
E coli
ESKAPEE bacteria
Gram-negative bacteria
Gram-positive bacteria
Infectious diseases
Life Sciences
Medicine
mycobacterium
Nosocomial infections
Pathogens
Pharmacy and materia medica
Quinoline
R
RS1-441
Staphylococcus infections
Tuberculosis
Quinoline
mycobacterium
nosocomial infections
ESKAPEE bacteria
tuberculosis
ISSN:1424-8247, 1424-8247
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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 4c–4h and 4k/4l) or E. coli (MIC = 32–64 µg/mL for 4q–4v) according to the global lipophilicity of these compounds.
AbstractList 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 4c−4h and 4k/4l) or E. coli (MIC = 32−64 µg/mL for 4q−4v) according to the global lipophilicity of these compounds.
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 4c-4h and 4k/4l) or E. coli (MIC = 32-64 µg/mL for 4q-4v) according to the global lipophilicity of these compounds.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 4c-4h and 4k/4l) or E. coli (MIC = 32-64 µg/mL for 4q-4v) according to the global lipophilicity of these compounds.
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 4c–4h and 4k/4l) or E. coli (MIC = 32–64 µg/mL for 4q–4v) according to the global lipophilicity of these compounds.
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 which have been identified as good candidates against ESKAPEE (Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, Enterobacter spp. and bacteria. Secondly, a new series was designed and assessed against the same bacteria strains, taking the pair of enantiomers / as the lead. More than twenty compounds were prepared through a five-step asymmetric synthesis with good enantiomeric excesses (>90%). Interestingly, all compounds of series were efficient on with MIC = 2-16 µg/mL, while series was less active. Both series and were generally more active than mefloquine against the ESKAPEE bacteria. The quinolines were either active against Gram-positive bacteria (MIC ≤ 4 µg/mL for - and / ) or (MIC = 32-64 µg/mL for - ) according to the global lipophilicity of these compounds.
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 mu g/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 mu g/mL for 4c-4h and 4k/4l) or E. coli (MIC = 32-64 mu g/mL for 4q-4v) according to the global lipophilicity of these compounds.
Author Catherine Mullié
Alexandra Dassonville-Klimpt
Pascal Sonnet
Sandrine Castelain
Pierre Laumaillé
Sophie Da-Nascimento
Claire Andréjak
François Peltier
AuthorAffiliation 2 Department of Bacteriology, Amiens University Hospital, 80054 Amiens, France
3 Respiratory and Intensive Care Unit, University Hospital Amiens, 80054 Amiens, France
1 AGIR, EA 4294, UFR of Pharmacy, Jules Verne University of Picardie, 80037 Amiens, France; pierre.laumaille@etud.u-picardie.fr (P.L.); peltier.francois@chu-amiens.fr (F.P.); catherine.mullie@u-picardie.fr (C.M.); andrejak.claire@chu-amiens.fr (C.A.); sophie.da-nascimento@u-picardie.fr (S.D.-N.); sandrine.castelain@u-picardie.fr (S.C.)
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Contributor Agents infectieux, résistance et chimiothérapie - UR UPJV 4294 (AGIR ) ; Université de Picardie Jules Verne (UPJV)-CHU Amiens-Picardie
Laboratoire de Virologie CHU Amiens
Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UMR CNRS 7378 (LG2A )
Université de Picardie Jules Verne (UPJV)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS)
CHU Amiens-Picardie
Université de Picardie Jules Verne (UPJV)-CHU Amiens-Picardie
Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UMR CNRS 7378 (LG2A ) ; Université de Picardie Jules Verne (UPJV)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS)
Laboratoire de Virologie [CHU Amiens] ; CHU Amiens-Picardie
Agents infectieux, résistance et chimiothérapie - UR UPJV 4294 (AGIR )
Université de Rennes 2 (UR2)
Université de Rennes 2 - UFR Arts, Lettres, Communication (UR2 UFRALC) ; Université de Rennes 2 (UR2)
Université de Rennes 2 - UFR A
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Copyright 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.
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Issue 2
Keywords Quinoline
mycobacterium
nosocomial infections
ESKAPEE bacteria
tuberculosis
Language English
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Snippet The lack of antibiotics with a novel mode of action associated with the spread of drug resistant bacteria make the fight against infectious diseases...
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StartPage 91
SubjectTerms [CHIM]Chemical Sciences
[SDV]Life Sciences [q-bio]
Antibiotics
Antimicrobial agents
Bacteria
Chemical Sciences
Drugs
E coli
ESKAPEE bacteria
Gram-negative bacteria
Gram-positive bacteria
Infectious diseases
Life Sciences
Medicine
mycobacterium
Nosocomial infections
Pathogens
Pharmacy and materia medica
Quinoline
R
RS1-441
Staphylococcus infections
Tuberculosis
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Title Synthesis and Study of New Quinolineaminoethanols as Anti-Bacterial Drugs
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