Quinolone antibacterial agents. Synthesis and structure-activity relationships of 8-substituted quinoline-3-carboxylic acids and 1,8-naphthyridine-3-carboxylic acids

Sanchez, Joseph P.; Domagala, John M.; Hagen, Susan E.; Heifetz, Carl L.; Hutt, Marland P.; Nichols, Jeffry B.; Trehan, Ashok K.

doi:10.1021/jm00400a016

Cited by 143 publications

(77 citation statements)

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“…This chemical subclass of the quinolone antibacterial agents has, in general, demonstrated much improved in vivo efficacy in animals and superior overall pharmacokinetics in mice and humans (4,5,10,11). Preliminary data indicate that PD 131112, the prodrug of PD 131628, possesses a high degree of effectiveness in in vivo models of infection (12).…”

Section: Resultsmentioning

confidence: 99%

In vitro antibacterial activities of PD 131628, a new 1,8-naphthyridine anti-infective agent

Cohen¹,

Huband²,

Mailloux³

et al. 1991

Antimicrob Agents Chemother

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PD 131628 is a new aminopyrrolidine-substituted fluorocyclopropyl naphthyridine quinolone which possesses high in vitro activity against a wide spectrum of bacterial species. The MICs for .90% of strains were 0.125 to 0.25 ,ug/ml for staphylococci, Streptococcus pyogenes, and S. pneumoniae; 0.5 ,ug/ml for S. agalactiae and Enterococcus faecalis; 0.125 jug/ml for members of the family Enterobacteriaceae and Acinetobacter spp.; 0.5 ,Lg/mI for Pseudomonas aeruginosa; and <0.03 ,ug/ml for Haemophilus influenzae, Moraxella (Branhamella) catarrhalis, and Neisseria gonorrhoeae. In these in vitro comparisons with ciprofloxacin, PD 131628 is more active against gram-positive organisms, approximately equivalent against gram-negative organisms, and, like most other quinolones, relatively inactive against gram-negative anaerobes. In most instances, the in vitro potency of PD 131628 exceeded those of widely used compounds:

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Section: Resultsmentioning

confidence: 99%

In vitro antibacterial activities of PD 131628, a new 1,8-naphthyridine anti-infective agent

Cohen¹,

Huband²,

Mailloux³

et al. 1991

Antimicrob Agents Chemother

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“…The most popular heterocycles employed at position 7 are aminopyrrolidines and piperazines. Anti-bacterial agents that contain an aminopyrrolidine moiety are tosufloxacin, clinafloxacin, Du6859a, Bay 3 118 and several compounds from the Parke-Davis company [6]. In contrast, the piperazine substituent is found on ciprofloxacin, lomefloxacin, temafloxacin, sparfloxacin and BMY 40062.…”

Section: Positionmentioning

confidence: 99%

Quinolones: structure-activity relationships and future predictions

Tillotson

1996

Journal of Medical Microbiology

129

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“…PD 117,596 is a recently synthesized, orally administered bactericidal antibiotic of the fluoroquinolone class (8). The structural formulas of PD 117,596 and nalidixic acid are shown in Fig.…”

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confidence: 99%

“…The substitution of a 3-amino pyrrolidine side chain for the piperazine moiety of other active agents also improves gram-positive activity and maintains the high tissue absorption associated with the piperazine group. A cyclopropyl group at position 1 contributes to activity against gram-negative bacilli (8). The currently studied quinolone compounds are known to be active against many gram-negative microorganisms (1)(2)(3)(4)(5)(6)(7)9).…”

mentioning

confidence: 99%

In vitro activities of PD 117,596 and reference antibiotics against 448 clinical bacterial strains

Smith

Baltch

Hammer

et al. 1988

Antimicrob Agents Chemother

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The in vitro activity of PD 117,596, a new fluoroquinolone antibiotic, was tested against 448 bacterial isolates (15 genera) by agar dilution (inoculum, 104 CFU per spot). The activity of PD 117,596 was compared with that of 15 antibiotics against 327 gram-negative strains and with that of 8 other antibiotics against 121 gram-positive strains. PD 117,596 demonstrated the best activity against Klebsiella spp., Enterobacter spp., Acinetobacter spp., Serratia marcescens, and Branhamella catarrhalis (MICs for 90% of the isolates [MIC90s], 0.008 to 0.25 ,ug/ml). PD 117,596 (MIC90, 0.25 ,ug/ml) was at least twofold more active than ciprofloxacin against Pseudomonas aeruginosa and Pseudomonas spp. PD 117,596 and ciprofloxacin were similar in activity against Escherichia coli, Proteus mirabilis, Haemophilus influenzae, H. parainfluenzae, Neisseria gonorrhoeae, Legion-ella pneumophila, and Campylobacterjejuni (MIC90, 0.002 to 0.125 ,Lg/ml). PD 117,596 was more active than ciprofloxacin against streptococcal groups A, B, C, and G, S. pneumoniae, and enterococci (MIC90s, 0.06 to 0.125 ,ig/ml). Against Staphylococcus aureus, including methicillin-resistant isolates, PD 117,596 (MIC90s, 0.03 to 0.06 tig/ml) was 4-to 16-fold more active than ciprofloxacin and was most active against Corynebacterium spp. PD 117,596 appears to be the most active fluoroquinolone to date, with excellent activity against gram-positive bacteria and enhanced activity against gram-negative aerobic-facultative bacteria.

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Quinolone antibacterial agents. Synthesis and structure-activity relationships of 8-substituted quinoline-3-carboxylic acids and 1,8-naphthyridine-3-carboxylic acids

Cited by 143 publications

References 0 publications

In vitro antibacterial activities of PD 131628, a new 1,8-naphthyridine anti-infective agent

In vitro antibacterial activities of PD 131628, a new 1,8-naphthyridine anti-infective agent

Quinolones: structure-activity relationships and future predictions

In vitro activities of PD 117,596 and reference antibiotics against 448 clinical bacterial strains

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