Synthesis of norfloxacin analogues catalyzed by Lewis and Brönsted acids: An alternative pathway

Leyva, Socorro; Hernández, Hiram

doi:10.1016/j.jfluchem.2010.07.002

Cited by 14 publications

(9 citation statements)

References 30 publications

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“…The N -ethyl group was introduced with Et-I under weakly basic conditions in 85% yield [36]. We initially introduced the piperazine unit in a quantitative yield with unprotected piperazine (not shown) [37–38]. However, purification and isolation were problematic and we found it more convenient to use Boc-piperazine (70% yield) to obtain 11 .…”

Section: Resultsmentioning

confidence: 99%

Cyclopropanation–ring expansion of 3-chloroindoles with α-halodiazoacetates: novel synthesis of 4-quinolone-3-carboxylic acid and norfloxacin

Peeters

Berntsen

Rongved

et al. 2019

Beilstein J. Org. Chem.

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Section: Resultsmentioning

confidence: 99%

Cyclopropanation–ring expansion of 3-chloroindoles with α-halodiazoacetates: novel synthesis of 4-quinolone-3-carboxylic acid and norfloxacin

Peeters

Berntsen

Rongved

et al. 2019

Beilstein J. Org. Chem.

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“…A general procedure for the synthesis of difluoroboryl 1ethyl-6,7-difluoro-1,4-dihydroquinoline-3-carboxylate 2 is presented as a Gould-Jacobs cyclization process, starting from 2,3-difluoroaniline 1, followed by N-alkylation and ester group moiety transformation into boron complex fluoroquinolone 2, obtaining a molecule with high regioselectivity in C-7 position (Figure 1) [24].…”

Section: Resultsmentioning

confidence: 99%

“…Fluoroquinolone-boron complex 2 was synthesized according to Leyva et al method [24]. 332.85 μmol of the fluoroquinolone 2 and 0.5 mmol of the heterocycle (3,5-diethoxycarbonyl-2,6-dimethyl-1,4dihydropyridine, uracil, 5,5-diphenylhydantoine, benzimi dazoleor1,2,3,4-tetrahydrocarbazole) were added in 1.5 mL of DMSO (for 3a-d, f ) or CH 3 CN (for 3e) and 69.4 μL of TEA solution.…”

Section: Synthesismentioning

confidence: 99%

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Synthesis of Hybrid Fluoroquinolone-Boron Complexes and Their Evaluation in Cervical Cancer Cell Lines

Hernández‐López

Sánchez-Miranda

Araujo-Huitrado

et al. 2019

Journal of Chemistry

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Quinolones are a family of antimicrobial agents that have been used in antibacterial and anticancer chemotherapy. Fluoroquinolone targets DNA gyrase and topoisomerase IV enzymes affecting several cellular processes, like cell death and proliferation; the best way to act is in the form of carboxylic acid or, recently, as quinolone-metal complex. In this work, the use of boron is shown as an alternative of metal to form a complex by incorporating to fluoroquinolone as an electron withdrawing substituent to activate the C-7 position chemoselectively for the production of new fluoroquinolone hybrids and test their effects on cell proliferation. Fluoroquinolone-boron complexes were synthesized according to the Gould-Jacobs cyclization method, and five hybrid fluoroquinolone-boron compounds were obtained by S N Ar reaction, yielding 31 to 46%, at 80°C, and in 10 to 25 hours of reaction. e effect of the five fluoroquinolone-boron hybrids was evaluated in cervical cancer cell lines by cell proliferation assay. 7-hydantoin-fluoroquinolone-boron and 7-dihydropyridine-fluoroquinolone-boron complexes showed the strongest effect according to dose-response assay, respectively. e fluoroquinolone-boron hybrid complex showed proliferation inhibition in SiHa and CasKi cells, opening the possibility to use them as potential agents for the treatment of cancer.

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“…Experiments proved that the quenching was a static process due to hydrophobic and electrostatic interactions which could induce conformational changes to BSA [55]. The interaction between Ce 3+ ions and carbonyl group was used in order to synthesize some quinolone antibiotic norfloxacin analogues through a new pathway [184].…”

Section: Other Applicationsmentioning

confidence: 99%

Quinolone Complexes with Lanthanide Ions: An Insight into their Analytical Applications and Biological Activity

2020

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Quinolones comprise a series of synthetic bactericidal agents with a broad spectrum of activity and good bioavailability. An important feature of these molecules is their capacity to bind metal ions in complexes with relevant biological and analytical applications. Interestingly, lanthanide ions possess extremely attractive properties that result from the behavior of the internal 4f electrons, behavior which is not lost upon ionization, nor after coordination. Subsequently, a more detailed discussion about metal complexes of quinolones with lanthanide ions in terms of chemical and biological properties is made. These complexes present a series of characteristics, such as narrow and highly structured emission bands; large gaps between absorption and emission wavelengths (Stokes shifts); and long excited-state lifetimes, which render them suitable for highly sensitive and selective analytical methods of quantitation. Moreover, quinolones have been widely prescribed in both human and animal treatments, which has led to an increase in their impact on the environment, and therefore to a growing interest in the development of new methods for their quantitative determination. Therefore, analytical applications for the quantitative determination of quinolones, lanthanide and miscellaneous ions and nucleic acids, along with other applications, are reviewed here.

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Synthesis of norfloxacin analogues catalyzed by Lewis and Brönsted acids: An alternative pathway

Cited by 14 publications

References 30 publications

Cyclopropanation–ring expansion of 3-chloroindoles with α-halodiazoacetates: novel synthesis of 4-quinolone-3-carboxylic acid and norfloxacin

Cyclopropanation–ring expansion of 3-chloroindoles with α-halodiazoacetates: novel synthesis of 4-quinolone-3-carboxylic acid and norfloxacin

Synthesis of Hybrid Fluoroquinolone-Boron Complexes and Their Evaluation in Cervical Cancer Cell Lines

Quinolone Complexes with Lanthanide Ions: An Insight into their Analytical Applications and Biological Activity

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