Synthesis, physicochemical characterization and antibacterial activity of novel (benzoylamino)methyl derivatives of quinolones

Breznica-Selmani, Pranvera; Mladenovska, Kristina; Dräger, Gerald; Mikhova, B.M.; Panovski, Nikola; Kaftandzieva, Ana; Kavrakovski, Zoran; Hoxha, Ahmet; Sheqerxhiu, Nardi; Pavlova, Maja Jurhar; Popovski, Emil

doi:10.20450/mjcce.2016.919

Cited by 4 publications

(3 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A previous correlation study reported that passive diffusion is not the defining mechanism for fluoroquinolone entry to bacterial cells minimizing the role of lipophilicity as observed in the current study. 18 Similarly, heat of formation and Gibbs energy showed weak correlations with the activity against S. aureus, whereas they showed weak or no impact on the activity against different gram-negative strains. Change in Gibbs free energy is usually negative, indicating that the complex formation between a compound and target enzyme is spontaneous.…”

Section: Calculation Of Lipophilicity Polarizability and Topology Pmentioning

confidence: 98%

New N -4 piperazinyl derivatives of norfloxacin: design, synthesis, and correlation of calculated physicochemical parameters with antibacterial activity

Abuo‐Rahma¹,

Abbas²,

Shoman³

et al. 2018

Turk J Chem

View full text Add to dashboard Cite

A group of N − 4 piperazinyl derivatives of norfloxacin was synthesized and identified by different spectroscopic techniques. The N − 4 piperazinyl substituent in target compounds 2a-2k, 3a-3c, and 4a and 4b was designed to have different electronic, steric, and physicochemical properties. The antibacterial activity of the newly synthesized compounds was evaluated against Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumoniae, and Staphylococcus aureus strains using norfloxacin as a reference. Results showed that most of the tested compounds had higher activity against E. coli and K. pneumoniae than norfloxacin, whereas only five derivatives were more active against P. aeruginosa. On the other hand, all derivatives were less active than norfloxacin against S. aureus. The biological activity of the target compounds, expressed in log MIC, is correlated with lipophilicity, polarizability, and topology parameters. Results showed that none of the calculated parameters could determine the biological activity. Consequently, the total volume of the molecule, bulkiness at C-7, electronic factors, and lipophilicity are important factors that should be considered in the design of new fluoroquinolones.

show abstract

Section: Calculation Of Lipophilicity Polarizability and Topology Pmentioning

confidence: 98%

New N -4 piperazinyl derivatives of norfloxacin: design, synthesis, and correlation of calculated physicochemical parameters with antibacterial activity

Abuo‐Rahma¹,

Abbas²,

Shoman³

et al. 2018

Turk J Chem

View full text Add to dashboard Cite

show abstract

“…[3] The chemical shifts and coupling constants of the fluoro-quinolone-piperazinyl moiety of ciprofloxacin and its derivatives showed very close values indicating that the benzamidomethyl substituents do not change the stereochemical behaviour and electronic structure of the parent compound. [3] Any information about the structure of these widely used antibiotics would be essential for a complete understanding of their biological activity. Due to the Correction added on 18 March 2019, after first online publication: A prefix 'S' has been added to the pagination of this article, so the page range has changed from 75-84 to S75-S84.…”

Section: Introductionmentioning

confidence: 97%

“…Recently, a series of derivatives of ciprofloxacin with novel benzamidomethyl substituents at N4′ of the piperazine ring have been synthesized as potential prodrugs with higher lipophilicity than the leading compound, and their structures were characterized with the help of 1D and 2D NMR spectra . The chemical shifts and coupling constants of the fluoro‐quinolone‐piperazinyl moiety of ciprofloxacin and its derivatives showed very close values indicating that the benzamidomethyl substituents do not change the stereochemical behaviour and electronic structure of the parent compound …”

Section: Introductionmentioning

confidence: 99%

Calculations of ¹³C NMR chemical shifts and F–C coupling constants of ciprofloxacin

Koch

Stamboliyska

Mikhova

et al. 2019

Magnetic Reson in Chemistry

Self Cite

View full text Add to dashboard Cite

Ciprofloxacin is a widely used fluoroquinolone antibiotic. In this work, a comprehensive evaluation of MP2 and DFT with different functionals and basis sets was carried out to select the most suitable level of theory for the study of the NMR properties of ciprofloxacin. Their relative predictive capabilities were evaluated comparing the theoretically predicted and experimental spectral data. Our computational results indicated that in contrast to the solid state, the molecule of ciprofloxacin does not exist as a zwitterion in gaseous state. The results of the calculations of the chemical shifts most close to the experimental were obtained with B3LYP/aug‐cc‐pVDZ. The F–C coupling constants were calculated systematically with different DFT methods and several basis sets. In general, the calculations of the coupling constants with the BHandH computational method including the applied in this work 6‐311++G**, EPRII, and EPRIII basis sets showed a good reproducibility of the experimental values of the coupling constants.

show abstract

Computational aspects of ¹⁹F NMR

Krivdin¹

2020

Russ. Chem. Rev.

View full text Add to dashboard Cite

This review covers most recent advances in computation of 19F NMR chemical shifts and spin – spin coupling constants involving 19F nucleus calculated at different levels of theory. It deals mainly with electronic and stereochemical effects influencing these parameters, with a special emphasis on practical applications of such calculations. For 19F NMR chemical shifts, a good deal of attention is focused on less common solid state studies, in addition to much more popular liquid state data. For spin – spin coupling constants, the main interest is concentrated on the most popular 19F–1H, 19F–13C and 19F–19F couplings providing marked stereochemical behaviour. The bibliography includes 149 references. In memory of Professor Rubén Horacio Contreras, to commemorate his achievements in the field of theoretical and computational 19F NMR.

show abstract

Synthesis, physicochemical characterization and antibacterial activity of novel (benzoylamino)methyl derivatives of quinolones

Cited by 4 publications

References 40 publications

New N -4 piperazinyl derivatives of norfloxacin: design, synthesis, and correlation of calculated physicochemical parameters with antibacterial activity

New N -4 piperazinyl derivatives of norfloxacin: design, synthesis, and correlation of calculated physicochemical parameters with antibacterial activity

Calculations of ¹³C NMR chemical shifts and F–C coupling constants of ciprofloxacin

Computational aspects of ¹⁹F NMR

Contact Info

Product

Resources

About

Synthesis, physicochemical characterization and antibacterial activity of novel (benzoylamino)methyl derivatives of quinolones

Cited by 4 publications

References 40 publications

New N -4 piperazinyl derivatives of norfloxacin: design, synthesis, and correlation of calculated physicochemical parameters with antibacterial activity

New N -4 piperazinyl derivatives of norfloxacin: design, synthesis, and correlation of calculated physicochemical parameters with antibacterial activity

Calculations of 13C NMR chemical shifts and F–C coupling constants of ciprofloxacin

Computational aspects of 19F NMR

Contact Info

Product

Resources

About

Calculations of ¹³C NMR chemical shifts and F–C coupling constants of ciprofloxacin

Computational aspects of ¹⁹F NMR