Synthesis and antibacterial activities of new fluoroquinolones based on ciprofloxacin structure (original) (raw)
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Synthesis and antimicrobial activity of some novel ciprofloxacin analogues
Journal of Pharmacy Research, 2015
A new class of 3,5-disubstituted pyrazoles and isoxazoles were prepared from the Michael acceptors 1-furanyl / thiophenyl / pyridinyl-3-indole-prop-2-en-1-ones under ultrasonication and evaluated for antimicrobial activity. Amongst all the tested compounds fluoro substituted thiophene linked compounds 12b and 18b displayed promising antibacterial activity particularly against Bacillus subtilis and antifungal activity against Aspergillus niger. Furthermore, compounds with more number of electron withdrawing groups showed higher antimicrobial activity. This result indicates that compounds 12b and 18b can be used as lead compounds in the future studies.
Molecular structures of new ciprofloxacin derivatives
Journal of Molecular Structure, 2002
Two new derivatives from the ciprofloxacin fluoroquinoline family, 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-methylcarbamate and 1-cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-(3-oxopyrazolo)[4,3-c]quinoline, were synthesised, tested for antibacterial activity and crystallised. Their molecular and crystal structures were determined. Tests in vitro reveal lower activities than for ciprofloxacin. Characteristic structural features of these compounds are comparable to data for other known fluoroquinolines. The bicyclic quinoline ring is planar in both compounds; the carbamate
Iranian Journal of …, 2011
Novel analogues of N-piperazinyl fluoroquinolones were prepared and evaluated against a panel of Gram-positive and Gram-negative bacteria, to study the effect of introducing bulky anthracene and phenanthrene moieties on the antibacterial effects of norfloxacin, ciprofloxacin and gatifloxacin. Although most of the novel synthesized compounds had lower antibacterial effects, some derivatives showed better activity in comparison with mother drugs based on molar concentration; for example, the 3-acetyl phenanthrene analogue of norfloxacin was more effective than E. coli and K. pneumonia.
Preparation and antibacterial evaluation of decarboxylated fluoroquinolones
Bioorganic & Medicinal Chemistry Letters, 2011
a b s t r a c t Decarboxylated ciprofloxacin (3) has been reported in the literature to have antibacterial activities against Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, Bacillus subtilis, Enterobacter cloacae, Serratia marcescens and especially potent activity against Escherichia coli. Herein, we report our syntheses of 3 and five additional decarboxylated fluoroquinolones (FQs). We have re-evaluated the antibacterial activity of these FQs. In contrast to previously reported data, none of these decarboxylated fluoroquinolones showed significant antibacterial activity in our assays using both the broth dilution and agar methods. Our study confirmed that the presence of a carboxylic acid group at the 3position of the fluoroquinolone scaffold is essential for antibacterial activity.
2018
In the present study, a series of 1-cyclopropyl-7-[4-(2,6-dimethylpyrimidin-2-yl-diazenyl)-piperzin-1-yl]-6-fluoro-4-oxo1,4-dihydroquinolone-3-carboxylic acid, 1-cyclopropyl-7-[4-(2,6-dimethoxypyrimidin-2-yl-diazenyl)-piperzin-1-yl]-6fluoro-4-oxo-1,4-dihydroquinolone-3-carboxylic acid and their dione derivatives have been synthesized in moderate yield. The newly synthesized compounds 5a-j have been characterized by IR, H NMR and elemental analysis. These compounds have been evaluated for their in vitro antibacterial activity against some gram-positive and gram-negative bacteria using conventional agar-dilution method. The antibacterial data of the newly synthesized compounds indicate that some of them showed better antibacterial activity as compared to their reference drug ciprofloxacin.
Design, Synthesis and Docking Studies of a Novel Ciprofloxacin Analogue as an Antimicrobial AGENT
E-Journal of Chemistry, 2012
The carboxylic acid group of ciprofloxacin was modified and amino mercapto triazole was substituted. The compound was confirmed by physical parameters (solubility, melting point), chromatographic methods (TLC) and consistent with its IR &1HNMR spectra. The synthesized analogue was screened for antibacterial activity against one gram positive & two gram negative species. The compound exhibited good antibacterial effect towards gram negative species when compared to the standard ciprofloxacin. At the same time the analogue was retaining antibacterial activity towards gram positive species when compared to standard ciprofloxacin. The molecular docking studies showed a good correlation between their antibacterial activity and autodock binding free energy.