Structure-Activity Relationships of Fluoro-4-Quinolones

Mitscher, L. A.; Devasthale, Pratik; Zavod, Robin M.

doi:10.1007/978-1-4471-3449-7_9

Cited by 23 publications

(23 citation statements)

References 34 publications

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“…Following the discovery of the fluorinated quinolone norfloxacin [19], considerable progress in the therapeutic use of quinolones has been made, and more than 10,000 anologues have been described [20]. These compounds are known to target specifically DNA gyrase, a bacterial type II topoisomerase [21].…”

Section: Introductionmentioning

confidence: 99%

A New Fluoroquinolone Derivative Exhibits Inhibitory Activity against Human Immunodeficiency Virus Type 1 Replication

et al. 1999

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The inhibitory activity of several fluoroquinolone antibiotics against human immunodeficiency virus type 1 (HIV-1) replication was investigated. R-71762, (±) 9-fluoro-3-fluoromethyl-2,3-dihydro-10-[4-(2-pyridyl)-1-piperazinyl]-7-oxo-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid, protected MT-4 cells from HIV-1-induced cytopathic effects. Furthermore, the compound inhibited virus replication both in acutely and in chronically HIV-1-infected cells. On the other hand, ofloxacin, levofloxacin, ciprofloxacin, norfloxacin and enoxacin, that were previously reported to be protective against HIV-1-induced cytopathic effects, did not show any protective activity in our assay system. These results indicate that R-71762 is a novel inhibitor of HIV-1 replication and is effective even in HIV-1 chronically infected cells.

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Section: Introductionmentioning

confidence: 99%

A New Fluoroquinolone Derivative Exhibits Inhibitory Activity against Human Immunodeficiency Virus Type 1 Replication

et al. 1999

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“…Quinolone derivatives employed as anti-FIV agents and compounds employed as anti-microbial agents share an important common structural feature: a carboxyl group at the C-3 position [1,22]. However, other structural features of potent anti-FIV quinolone derivatives, as suggested in this study, were quite different from those of the anti-microbial quinolone derivatives.…”

Section: Discussionmentioning

confidence: 59%

8-Difluoromethoxy-4-Quinolone Derivatives as Anti-Feline Immunodeficiency Virus (FIV) Agents: Important Structural Features for Inhibitory Activity of FIV Replication

Kashiwase¹,

Katsube

Kimura

et al. 2000

The Journal of Veterinary Medical Science

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ABSTRACT. The inhibitory activities of various 8-difluoromethoxy-4-quinolone derivatives against feline immunodeficiency virus (FIV) replication in the chronically infected cell line P-CrFK were investigated. Certain derivatives were found to inhibit FIV production from PCrFK cells in a dose-dependent manner without exhibiting cytotoxic effects at inhibitory concentrations. Based on this study, the structures important for anti-FIV activity are suggested to be (i) a carboxyl group at position C-3, and (ii) an aromatic modification at position 4 of the C-7 piperazinyl moiety.-KEY WORDS: antiviral agent, arylpiperazinyl fluoroquinolone, feline immunodeficiency virus (FIV), inhibitor of FIV replication.

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“…The antibacterial activity of quinolones depends not only on the bicyclic heteroaromatic system (pyridone-β-carboxylic acid nucleus and the aromatic ring), but also on the nature of peripheral substituents and their spatial relationship (Chu and Fernandes 1989;Mitscher et al 1993;Bryskier and Chantot 1995). Nalidixic acid is a non-fluorinated molecule belonging to what is known as group IIA (Bryskier and Chantot 1995).…”

Section: Discussionmentioning

confidence: 99%

Role of the outer membrane in the accumulation of quinolones bySerratia marcescens

Berlanga¹,

Ruiz²,

Hernández-Borrell³

et al. 2000

Can. J. Microbiol.

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Accumulation of four quinolones by Serratia marcescens was measured fluorometrically. The passage of quinolones through the outer membrane was studied in both lipopolysaccharide-deficient and porin-deficient mutants. The lipopolysaccharide (LPS) layer formed a partially effective barrier for highly hydrophobic quinolones such as nalidixic acid. Quinolones with a low relative hydrophobicity coefficient seemed to pass preferentially through the water-filled Omp3 porin channels. Results were confirmed when Omp3 was cloned in a porin-defective Escherichia coli.

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Structure-Activity Relationships of Fluoro-4-Quinolones

Cited by 23 publications

References 34 publications

A New Fluoroquinolone Derivative Exhibits Inhibitory Activity against Human Immunodeficiency Virus Type 1 Replication

A New Fluoroquinolone Derivative Exhibits Inhibitory Activity against Human Immunodeficiency Virus Type 1 Replication

8-Difluoromethoxy-4-Quinolone Derivatives as Anti-Feline Immunodeficiency Virus (FIV) Agents: Important Structural Features for Inhibitory Activity of FIV Replication

Role of the outer membrane in the accumulation of quinolones bySerratia marcescens

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