Synthesis and antitubercular activity of lipophilic moxifloxacin and gatifloxacin derivatives

Twelve lipophilic moxifloxacin or gatifloxacin new derivatives were synthetized, seven of them having MIC < 1.25 μg/mL. Fluoroquinolone (FQ) has a broad spectrum of activity against several bacteria, mycobacteria, parasites, and other diseases. Moxifloxacin and gatifloxacin are a new generation o...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2007-10, Vol.17 (20), p.5661-5664
Main Authors: de Almeida, Mauro V., Saraiva, Maurício F., de Souza, Marcus V.N., da Costa, Cristiane F., Vicente, Felipe R.C., Lourenço, Maria C.S.
Format: Article
Language:English
Subjects:
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antitubercular
Antitubercular Agents - chemical synthesis
Antitubercular Agents - chemistry
Antitubercular Agents - pharmacology
Aza Compounds - chemical synthesis
Aza Compounds - chemistry
Aza Compounds - pharmacology
Biological and medical sciences
Diamines
Fluoroquinolones
Fluoroquinolones - chemical synthesis
Fluoroquinolones - chemistry
Fluoroquinolones - pharmacology
Gatifloxacin
Lipids - chemistry
M. tuberculosis
Medical sciences
Molecular Structure
Moxifloxacin
N-Alkyl chains
Pharmacology. Drug treatments
Quinolines - chemical synthesis
Quinolines - chemistry
Quinolines - pharmacology
Streptococcus pneumoniae - drug effects
Structure-Activity Relationship
Structure–activity relationships
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Summary:Twelve lipophilic moxifloxacin or gatifloxacin new derivatives were synthetized, seven of them having MIC < 1.25 μg/mL. Fluoroquinolone (FQ) has a broad spectrum of activity against several bacteria, mycobacteria, parasites, and other diseases. Moxifloxacin and gatifloxacin are a new generation of fluoroquinolone agents with improved activity against Gram-negative and positive bacteria. As lipophilicity is an important consideration in the design and activity of novel antibacterial agents, we report in this work the synthesis and biological evaluation of 12 lipophilic moxifloxacin or gatifloxacin derivatives, by reaction of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid 13 with severals N-monoalkyl 1,2-ethanediamine or 1,3-propanediamine.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2007.07.073