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Lipophilic quinolone derivatives: Synthesis and in vitro antibacterial evaluation.
Sadowski, Elodie; Bercot, Beatrice; Chauffour, Aurélie; Gomez, Catherine; Varon, Emmanuelle; Mainardis, Mary; Sougakoff, Wladimir; Mayer, Claudine; Sachon, Emmanuelle; Anquetin, Guillaume; Aubry, Alexandra.
Afiliação
  • Sadowski E; Sorbonne Université, INSERM, Centre d'Immunologie et des Maladies Infectieuses, U1135, AP-HP, Hôpital Pitié-Salpêtrière, Centre National de Référence des Mycobactéries et de la Résistance des Mycobactéries aux Antituberculeux, F-75013 Paris, France; Sorbonne Université, École normale supérieure, PSL
  • Bercot B; Paris University, INSERM UMR1137, Infection, Antimicrobials, Modelling, Evolution, IAME, 16 rue Henri Huchard, 75870 Paris Cedex 18, France; French National Reference Centre for Bacterial Sexually Transmitted Infections, Associated Laboratory for Gonococci, Assistance Publique - Hôpitaux de Paris (A
  • Chauffour A; Sorbonne Université, INSERM, Centre d'Immunologie et des Maladies Infectieuses, U1135, AP-HP, Hôpital Pitié-Salpêtrière, Centre National de Référence des Mycobactéries et de la Résistance des Mycobactéries aux Antituberculeux, F-75013 Paris, France.
  • Gomez C; Laboratoire de Génomique, Bioinformatique et Chimie Moléculaire (EA7528), Equipe Chimie Moléculaire, Conservatoire National des Arts et Métiers (CNAM), HESAM Université, 2 rue Conté, 75003 Paris, France.
  • Varon E; Laboratory of Medical Biology, Centre Hospitalier Intercommunal de Créteil, 40 avenue de Verdun, 94010 Créteil, France; National Reference Center for Pneumococci, Centre Hospitalier Intercommunal de Créteil, 40 avenue de Verdun, 94010 Créteil, France.
  • Mainardis M; Paris University, INSERM UMR1137, Infection, Antimicrobials, Modelling, Evolution, IAME, 16 rue Henri Huchard, 75870 Paris Cedex 18, France; French National Reference Centre for Bacterial Sexually Transmitted Infections, Associated Laboratory for Gonococci, Assistance Publique - Hôpitaux de Paris (A
  • Sougakoff W; Sorbonne Université, INSERM, Centre d'Immunologie et des Maladies Infectieuses, U1135, AP-HP, Hôpital Pitié-Salpêtrière, Centre National de Référence des Mycobactéries et de la Résistance des Mycobactéries aux Antituberculeux, F-75013 Paris, France; AP-HP. Sorbonne-Université, Centre National de Réf
  • Mayer C; Department of Computer Science, ICube UMR 7357, CNRS, University of Strasbourg, 300 bd Sébastien Brant, 67400 Illkirch, France; Unité de Microbiologie Structurale, Institut Pasteur, CNRS UMR 3528, 25 rue du Docteur Roux, 75724 Paris Cedex 15, France; Université de Paris, 5 rue Thomas-Mann, 75013 Par
  • Sachon E; Sorbonne Université, École normale supérieure, PSL University, CNRS, Laboratoire des Biomolécules, LBM, 4 place Jussieu, 75252 Cedex 05 Paris, France; Sorbonne Université, MS(3)U Platform, Mass Spectrometry Sciences Sorbonne Université, 4 place Jussieu, 75252 Cedex 05 Paris, France.
  • Anquetin G; Université de Paris, ITODYS (Interfaces Traitements Organisation et DYnamique des Systèmes), CNRS, F-75006 Paris, France.
  • Aubry A; Sorbonne Université, INSERM, Centre d'Immunologie et des Maladies Infectieuses, U1135, AP-HP, Hôpital Pitié-Salpêtrière, Centre National de Référence des Mycobactéries et de la Résistance des Mycobactéries aux Antituberculeux, F-75013 Paris, France; Université de Paris, 5 rue Thomas-Mann, 75013 Pari
Bioorg Med Chem Lett ; 55: 128450, 2022 01 01.
Article em En | MEDLINE | ID: mdl-34774742
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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Texto completo: 1 Base de dados: MEDLINE Assunto principal: Quinolonas / Antibacterianos / Neisseria gonorrhoeae Idioma: En Revista: Bioorg Med Chem Lett Assunto da revista: BIOQUIMICA / QUIMICA Ano de publicação: 2022 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Quinolonas / Antibacterianos / Neisseria gonorrhoeae Idioma: En Revista: Bioorg Med Chem Lett Assunto da revista: BIOQUIMICA / QUIMICA Ano de publicação: 2022 Tipo de documento: Article