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6-Aminoquinolones: a New Class of Quinolone Antibacterials?
- Publication Year :
- 1995
-
Abstract
- A series of quinolone- and 1,8-naphthyridone-3-carboxylic acids, designed by previous QSAR studies and characterized by an amino group at the C-6 position instead of the usual fluorine atom, were synthesized for the first time and evaluated for in vitro antibacterial activity. All of the synthesized compounds maintain good activity against Gram-negative bacteria (Pseudomonas aeruginosa excluded), and those compounds having a thiomorpholine group as the C-7 substituent also have good activity against Gram-positive bacteria. Some aspects of structure-activity relationships associated with the C-1, C-5, C-7, and C-8 substituents are also discussed. Derivatives 18g and 38g displayed the best activity with geometric mean MICs of 0.45 and 0.66-0.76 micrograms/mL against Gram-negative and Gram-positive bacteria, respectively. This antimicrobial activity reflects their ability to inhibit bacterial DNA-gyrase. The results of this study show that, while the C-6 fluorine is still the preferred substituent, good activity can still be obtained by replacing it with an amino group.
- Subjects :
- DNA, Bacterial
4-Quinolones
biology
medicine.drug_class
Stereochemistry
Chemistry
Substituent
Microbial Sensitivity Tests
Gram-Positive Bacteria
Quinolone
Antimicrobial
biology.organism_classification
Chemical synthesis
Structure-Activity Relationship
chemistry.chemical_compound
Thiomorpholine
Anti-Infective Agents
Gram-Negative Bacteria
Drug Discovery
Aminoquinolines
medicine
Molecular Medicine
Antibacterial activity
Bacteria
Antibacterial agent
Subjects
Details
- Language :
- English
- Database :
- OpenAIRE
- Accession number :
- edsair.doi.dedup.....cf917ba9bf49056cb01e3ca0338a70bc