Antimicrobially Active Zn(II) Complexes of Reduced Schiff Bases Derived from Cyclohexane-1,2-diamine and Fluorinated Benzaldehydes—Synthesis, Crystal Structure and Bioactivity
A series of Schiff base ligands obtained by the condensation of <i>trans</i>-cyclohexane-1,2-diamine and fluorinated benzaldehydes were prepared, followed by their reduction with NaBH<sub>4</sub>. The reduced ligands were employed in the synthesis of zinc complexes of the gen...
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MDPI AG
2023-07-01
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| author | Bianka Oboňová Ladislav Habala Miroslava Litecká Peter Herich Andrea Bilková František Bilka Branislav Horváth |
| author_facet | Bianka Oboňová Ladislav Habala Miroslava Litecká Peter Herich Andrea Bilková František Bilka Branislav Horváth |
| author_sort | Bianka Oboňová |
| collection | DOAJ |
| description | A series of Schiff base ligands obtained by the condensation of <i>trans</i>-cyclohexane-1,2-diamine and fluorinated benzaldehydes were prepared, followed by their reduction with NaBH<sub>4</sub>. The reduced ligands were employed in the synthesis of zinc complexes of the general formula [ZnCl<sub>2</sub>(L)]. The structures of both the original and the reduced Schiff bases, as well as of the zinc complexes, were characterized by single-crystal X-ray analysis, along with NMR and IR spectroscopy. The antimicrobial activities of the reduced Schiff bases and their zinc complexes were evaluated in vitro against <i>E. coli</i>, <i>S. aureus</i>, and <i>C. albicans</i>. The compounds containing the 4-(trifluoromethylphenyl) moiety showed marked antibacterial activity. Interestingly, the antimicrobial effect of the zinc complex with this moiety was significantly higher than that of the corresponding free reduced ligand, comparable with ciprofloxacin used as standard. Thus, a synergic effect upon the complexation with zinc can be inferred. |
| first_indexed | 2024-03-11T00:53:53Z |
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| institution | Directory Open Access Journal |
| issn | 2075-1729 |
| language | English |
| last_indexed | 2024-03-11T00:53:53Z |
| publishDate | 2023-07-01 |
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| spelling | doaj.art-769c9486669745c8befdc664f0958a2f2023-11-18T20:09:35ZengMDPI AGLife2075-17292023-07-01137151610.3390/life13071516Antimicrobially Active Zn(II) Complexes of Reduced Schiff Bases Derived from Cyclohexane-1,2-diamine and Fluorinated Benzaldehydes—Synthesis, Crystal Structure and BioactivityBianka Oboňová0Ladislav Habala1Miroslava Litecká2Peter Herich3Andrea Bilková4František Bilka5Branislav Horváth6Department of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius University in Bratislava, Odbojárov 10, 832 32 Bratislava, SlovakiaDepartment of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius University in Bratislava, Odbojárov 10, 832 32 Bratislava, SlovakiaDepartment of Materials Chemistry, Institute of Inorganic Chemistry of the CAS, Husinec-Řež č.p. 1001, 250 68 Řež, Czech RepublicDepartment of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius University in Bratislava, Odbojárov 10, 832 32 Bratislava, SlovakiaDepartment of Cellular and Molecular Biology of Drugs, Faculty of Pharmacy, Comenius University in Bratislava, Odbojárov 10, 832 32 Bratislava, SlovakiaDepartment of Cellular and Molecular Biology of Drugs, Faculty of Pharmacy, Comenius University in Bratislava, Odbojárov 10, 832 32 Bratislava, SlovakiaNMR Laboratory, Faculty of Pharmacy, Comenius University in Bratislava, Odbojárov 10, 832 32 Bratislava, SlovakiaA series of Schiff base ligands obtained by the condensation of <i>trans</i>-cyclohexane-1,2-diamine and fluorinated benzaldehydes were prepared, followed by their reduction with NaBH<sub>4</sub>. The reduced ligands were employed in the synthesis of zinc complexes of the general formula [ZnCl<sub>2</sub>(L)]. The structures of both the original and the reduced Schiff bases, as well as of the zinc complexes, were characterized by single-crystal X-ray analysis, along with NMR and IR spectroscopy. The antimicrobial activities of the reduced Schiff bases and their zinc complexes were evaluated in vitro against <i>E. coli</i>, <i>S. aureus</i>, and <i>C. albicans</i>. The compounds containing the 4-(trifluoromethylphenyl) moiety showed marked antibacterial activity. Interestingly, the antimicrobial effect of the zinc complex with this moiety was significantly higher than that of the corresponding free reduced ligand, comparable with ciprofloxacin used as standard. Thus, a synergic effect upon the complexation with zinc can be inferred.https://www.mdpi.com/2075-1729/13/7/1516antimicrobial activitymetal complexesfluorinated compoundsmedicinal chemistrySchiff baseszinc |
| spellingShingle | Bianka Oboňová Ladislav Habala Miroslava Litecká Peter Herich Andrea Bilková František Bilka Branislav Horváth Antimicrobially Active Zn(II) Complexes of Reduced Schiff Bases Derived from Cyclohexane-1,2-diamine and Fluorinated Benzaldehydes—Synthesis, Crystal Structure and Bioactivity Life antimicrobial activity metal complexes fluorinated compounds medicinal chemistry Schiff bases zinc |
| title | Antimicrobially Active Zn(II) Complexes of Reduced Schiff Bases Derived from Cyclohexane-1,2-diamine and Fluorinated Benzaldehydes—Synthesis, Crystal Structure and Bioactivity |
| title_full | Antimicrobially Active Zn(II) Complexes of Reduced Schiff Bases Derived from Cyclohexane-1,2-diamine and Fluorinated Benzaldehydes—Synthesis, Crystal Structure and Bioactivity |
| title_fullStr | Antimicrobially Active Zn(II) Complexes of Reduced Schiff Bases Derived from Cyclohexane-1,2-diamine and Fluorinated Benzaldehydes—Synthesis, Crystal Structure and Bioactivity |
| title_full_unstemmed | Antimicrobially Active Zn(II) Complexes of Reduced Schiff Bases Derived from Cyclohexane-1,2-diamine and Fluorinated Benzaldehydes—Synthesis, Crystal Structure and Bioactivity |
| title_short | Antimicrobially Active Zn(II) Complexes of Reduced Schiff Bases Derived from Cyclohexane-1,2-diamine and Fluorinated Benzaldehydes—Synthesis, Crystal Structure and Bioactivity |
| title_sort | antimicrobially active zn ii complexes of reduced schiff bases derived from cyclohexane 1 2 diamine and fluorinated benzaldehydes synthesis crystal structure and bioactivity |
| topic | antimicrobial activity metal complexes fluorinated compounds medicinal chemistry Schiff bases zinc |
| url | https://www.mdpi.com/2075-1729/13/7/1516 |
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