Details
| Original language | English |
|---|---|
| Pages (from-to) | 179-197 |
| Number of pages | 19 |
| Journal | Macedonian Journal of Chemistry and Chemical Engineering |
| Volume | 35 |
| Issue number | 2 |
| Publication status | Published - 2016 |
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.
Keywords
- (Venzoylamino)methyl, Antimicrobial activity, Physicochemical properties, Quinolones, Structure
ASJC Scopus subject areas
- Chemistry(all)
- General Chemistry
- Chemical Engineering(all)
- General Chemical Engineering
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In: Macedonian Journal of Chemistry and Chemical Engineering, Vol. 35, No. 2, 2016, p. 179-197.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Synthesis, physicochemical characterization and antibacterial activity of novel (benzoylamino)methyl derivatives of quinolones
AU - Breznica-Selmani, P.
AU - Mladenovska, K.
AU - Dräger, G.
AU - Mikhova, B.
AU - Panovski, N.
AU - Kaftandzieva, A.
AU - Kavrakovski, Z.
AU - Hoxha, A.
AU - Sheqerxhiu, N.
AU - Pavlova, M. J.
AU - Popovski, E.
N1 - Copyright: Copyright 2018 Elsevier B.V., All rights reserved.
PY - 2016
Y1 - 2016
N2 - 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.
AB - 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.
KW - (Venzoylamino)methyl
KW - Antimicrobial activity
KW - Physicochemical properties
KW - Quinolones
KW - Structure
UR - http://www.scopus.com/inward/record.url?scp=85010021635&partnerID=8YFLogxK
U2 - 10.20450/mjcce.2016.919
DO - 10.20450/mjcce.2016.919
M3 - Article
AN - SCOPUS:85010021635
VL - 35
SP - 179
EP - 197
JO - Macedonian Journal of Chemistry and Chemical Engineering
JF - Macedonian Journal of Chemistry and Chemical Engineering
SN - 1857-5552
IS - 2
ER -