1031928-53-6Relevant articles and documents
Synthesis and study of new quinolineaminoethanols as anti-bacterial drugs
Laumaillé, Pierre,Dassonville-klimpt, Alexandra,Peltier, Fran?ois,Mullié, Catherine,Andréjak, Claire,Da-nascimento, Sophie,Castelain, Sandrine,Sonnet, Pascal
, (2019)
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.
Application of 2, 8-bis (trifluoromethyl)-4-hydroxyquinoline derivative in preparation and prevention and treatment of agricultural diseases
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Paragraph 0499-0502, (2021/04/07)
The invention discloses application of a 2, 8-bis (trifluoromethyl)-4-hydroxyquinoline derivative in preparation and prevention and treatment of agricultural diseases. Activity test results show that the compound has potential inhibitory activity on four plant pathogenic fungi including sclerotinia sclerotiorum, botrytis cinerea, fusarium graminearum and rhizoctonia solani, and can be developed as a bactericide.
Enantioselective synthesis method of 4-aminoalcoholquinoline derivatives and the use
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Page/Page column 13, (2012/08/28)
Mefloquine derivatives, contrary to chloroquine derivatives have not been widely studied to date. Consequently, mefloquine and its derivatives still remain very attractive synthetic targets. Although mefloquine is usually used clinically as a racemic mixture, some studies have shown that its (+)-enantiomer is more potent than the (-)-enantiomer. Moreover, the (-)-enantiomer is responsible for side effects due to reaction with the central nervous system adenosine receptors, while the (+)-enantiomer does no bind at this binding site. Recently, different libraries of racemate 4-aminoalcoholquinolines showed interesting anti-malarial activities. Herein, the present invention describes an enantiopure synthetic and straightforward route to prepare pure enantiomer 4-aminoalcoholquinoline derivatives through the 4-oxirane key-intermediate. A regioselective SN2 ring opening of this epoxide, by diverse amines, allows to obtain the corresponding (R) or (S) 4-aminoquinolines with good yields and enantiomeric excesses generally superior to 92%. The reported methodology appears suitable for the synthesis of a large number of pure enantiomer 4-aminoalcoholquinoline derivatives.
