The novel 1-(2-fluorovinyl)-4-quinolone-3-carboxylic acid derivatives Z-15a-c, E-15a-c, Z-16a-c, and E-16a-c, conformationally restricted analogues of fleroxacin (5), were synthesized, and their in vitro antibacterial activity was evaluated. A dehydrosulfenylation of a 2-fluoro-2-[(4-methoxyphenyl)sulfinyl]ethyl group was employed as a key step for the construction of a 2-fluorovinyl group at the N-1 position. It appeared evident that the Z-isomers Z-15a-c and Z-16a-c exhibited 2- to 32-fold more potent in vitro antibacterial activity than the corresponding E-isomers E-15a-c and E-16a-c. Furthermore, since Z-15b showed in vitro antibacterial activity and DNA gyrase inhibition comparable to that of 5, it was hypothesized that the conformation of Z-15b would be equivalent to the active conformer of 5. The results revealed that the antibacterial Z-1-(2-fluorovinyl)quinolone derivatives carry the novel N-1 substituent of the fluoroquinolones.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jm0402061 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Abdominal PP meshes coated with functional core-sheath biodegradable nanofibers with anticoagulant and antibacterial properties.
Biomater Adv
January 2025
Univ. Lille, CNRS, INRAE, Centrale Lille, UMR 8207 - UMET - Unité Matériaux et Transformations, F-59000 Lille, France. Electronic address:
Abdominal hernia repair is a common surgical procedure, involving in most cases the use of textile meshes providing a mechanical barrier to consolidate the damaged surrounding tissues and prevent the resurgence of the hernia. However, in more than half cases postoperative complications such as adhesions and infections occur at the surface of the mesh, leading to chronic pain for the patient and requiring the removal of the implant. One of the most promising strategies to reduce the risk of postoperative adhesions and infections is to add a physical barrier between the mesh and the abdominal walls.
View Article and Find Full Text PDFDevelopment of targeted antimicrobial peptides for Escherichia coli: Combining phage display and rational design for food safety application.
Food Chem
December 2024
Laboratory of Molecular Nutrition and Immunity, College of Animal Science and Technology, Northeast Agricultural University, Harbin, PR China. Electronic address:
The growing demand for minimally processed foods has heightened the risk of pathogenic contamination. Balancing antimicrobial efficacy with the preservation of probiotic activity remains a significant challenge. In this study, we employed phage display peptide library screening, combined with next-generation sequencing to identify the HIMPIQA domain, which selectively targets pathogenic Escherichia coli (E.
View Article and Find Full Text PDFNovel Fluoroquinolones With Pinane Moiety: Synthesis and Antimicrobial Activity.
Chem Biodivers
January 2025
Institute of Fundamental Medicine and Biology, Kazan Federal University, Kazan, Russia.
Here, we report a synthesis of fluoroquinolones carrying a monoterpene moiety at the C7 position of aromatic structure. The minimal inhibitory concentrations of fluoroquinolone fused with trans-3-hydroxy-cis-myrtanylamine 18 against Staphylococcus aureus (MSSA isolates) were two- to eightfold lower compared to moxifloxacin, although fourfold higher against MRSA isolates. The fluoroquinolone fused with (-)-nopylamine 16 was four- to eightfold less active on MSSA compared to moxifloxacin, while had similar activity on MRSA.
View Article and Find Full Text PDFRecent Updates on Antibacterial Quinolones: Green Synthesis, Mode of Interaction and Structure-Activity Relationship.
Chem Biodivers
January 2025
Department of Pharmaceutical Chemistry, MM College of Pharmacy, Maharishi Markandeshwar (Deemed to be University), Ambala, India.
Quinolone antibiotics are a crucial class of synthetic antibacterial agents, widely utilized due to their broad spectrum of antibacterial activity. Due to the development of antimicrobial resistance, the potency of quinolone drugs decreased. Many conventional methods have been developed to elevate amination rate and to improve yield.
View Article and Find Full Text PDFExtractive optimization of bioactive compounds in aerial parts of using Box-Behnken experimental design.
Nat Prod Res
January 2025
Postgraduate Program in Biotechnology Applied to Agriculture, University of Paraná, Umuarama, Brazil.
is known for its potential antioxidant and anti-inflammatory properties, attributed to triterpenes, flavonoids, and tannins. This study aimed to optimise the extraction process for aerial parts of using vortex extraction. A Box-Behnken experimental design coupled with response surface methodology was employed to evaluate the effects of three independent variables: sample-to-solvent ratio, velocity, and temperature.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!