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

Authors

  • Pranvera Breznica-Selmani Faculty of Medicine, University Hasan Prishtina, Mother Theresa n.n., 10 000 Prishtina,
  • Kristina Mladenovska Institute of Pharmaceutical Chemistry, Faculty of Pharmacy, Ss. Cyril and Methodius University, Mother Theresa 47, 1000 Skopje,
  • Gerald Dräger Institute of Organic Chemistry, Leibniz Universität Hannover, D-30167, Hannover,
  • Bozhana Mikhova Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev 9, 1113 Sofia,
  • Nikola Panovski Institute of Microbiology and Parasitology, Faculty of Medicine, Ss. Cyril and Methodius University, 50th Division 6, 1000 Skopje,
  • Ana Kaftandzieva Institute of Microbiology and Parasitology, Faculty of Medicine, Ss. Cyril and Methodius University, 50th Division 6, 1000 Skopje,
  • Zoran Kavrakovski Institute of Pharmaceutical Chemistry, Faculty of Pharmacy, Ss. Cyril and Methodius University, Mother Theresa 47, 1000 Skopje,
  • Ahmet Hoxha TreLab Quality Control Laboratory, Trepharm, Magjistralja Prishtina - Peje, M9 12050 Fushe Kosovo,
  • Nardi Sheqerxhiu TreLab Quality Control Laboratory, Trepharm, Magjistralja Prishtina - Peje, M9 12050 Fushe Kosovo,
  • Maja Jurhar Pavlova Institute of Pharmaceutical Chemistry, Faculty of Pharmacy, Ss. Cyril and Methodius University, Mother Theresa 47, 1000 Skopje,
  • Emil Popovski Institute of Chemistry, Faculty of Natural Sciences and Mathematics, Ss. Cyril and Methodius University, Arhimedova 5, Skopje,

DOI:

https://doi.org/10.20450/mjcce.2016.919

Keywords:

(benzoylamino)methyl, quinolones, structure, physicochemical properties, antimicrobial activity

Abstract

Herein we report the synthesis of different derivatives of (fluoro)quinolones norfloxacin, ciprofloxacin and pipemidic acid, by incorporating (benzoylamino)methyl on the free nitrogen of the pyperazinyl moiety. The compounds were structurally characterized by 1D and 2D NMR, FTIR and high-resolution mass spectroscopy. In addition, their physicochemical properties were a matter of interest to be correlated with their structure and antimicrobial activity in vitro. Their antimicrobial activities were screened against Gram-positive, Gram-negative bacteria and C. albicans. Higher distribution coefficients and consequently lower water solubility were determined for all synthesized compounds than the ones of the corresponding leading compounds. Inconsequential correlations between the lipophilicity of the compounds and MIC were observed, suggesting that passive diffusion is not the only mechanism for their penetration into bacterial cells. Further studies are needed to determine how substitutions in the (fluoro)quinolone moiety affect the primary target(s), substrate behavior in respect to bacterial transporters and overall bioavailability.

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Published

2016-10-12

How to Cite

Breznica-Selmani, P., Mladenovska, K., Dräger, G., Mikhova, B., Panovski, N., Kaftandzieva, A., Kavrakovski, Z., Hoxha, A., Sheqerxhiu, N., Jurhar Pavlova, M., & Popovski, E. (2016). Synthesis, physicochemical characterization and antibacterial activity of novel (benzoylamino)methyl derivatives of quinolones. Macedonian Journal of Chemistry and Chemical Engineering, 35(2), 179–197. https://doi.org/10.20450/mjcce.2016.919

Issue

Vol. 35 No. 2 (2016)

Section

Organic Chemistry

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