Lipophilic quinolone derivatives: Synthesis and in vitro antibacterial evaluation - Sorbonne Université
Journal Articles Bioorganic and Medicinal Chemistry Letters Year : 2022

Lipophilic quinolone derivatives: Synthesis and in vitro antibacterial evaluation

Abstract

This paper reports on the design of a series of 10 novel lipophilic piperazinyl derivatives of the 1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, their synthesis, their characterisation by 1H, 13C and 19F NMR, IR spectroscopy and HRMS, as well as their biological activity against bacteria of medical interest. Among these derivatives, 2 were as potent as the parent quinolone against Neisseriagonorrhoeae whereas all the compounds displayed lower activity than the parent quinolone against other bacteria of medical interest. Our results showing that the increased lipophilicity was deleterious for antibacterial activity may help to design new quinolone derivatives in the future, especially lipophilic quinolones which have been poorly investigated previously.
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Dates and versions

hal-03448562 , version 1 (25-11-2021)
hal-03448562 , version 2 (25-11-2021)

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Elodie Sadowski, Beatrice Bercot, Aurélie Chauffour, Catherine Gomez, Emmanuelle Varon, et al.. Lipophilic quinolone derivatives: Synthesis and in vitro antibacterial evaluation. Bioorganic and Medicinal Chemistry Letters, 2022, 55, pp.128450. ⟨10.1016/j.bmcl.2021.128450⟩. ⟨hal-03448562v2⟩
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