Novel Quaternary Ammonium Derivatives of 4-Pyrrolidino Pyridine: Synthesis, Structural, Thermal, and Antibacterial Studies
Six novel quaternary ammonium derivatives of 4-pyrrolidino pyridine were prepared and isolated via a facile one-pot synthesis and a simple purification procedure. The purity and the molecular structure of the 4-pyrrolidino pyridine derivatives were confirmed with <sup>1</sup>H and <su...
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MDPI AG
2020-04-01
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| Online Access: | https://www.mdpi.com/2073-4352/10/5/339 |
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| author | Rusi Rusew Vanya Kurteva Boris Shivachev |
| author_facet | Rusi Rusew Vanya Kurteva Boris Shivachev |
| author_sort | Rusi Rusew |
| collection | DOAJ |
| description | Six novel quaternary ammonium derivatives of 4-pyrrolidino pyridine were prepared and isolated via a facile one-pot synthesis and a simple purification procedure. The purity and the molecular structure of the 4-pyrrolidino pyridine derivatives were confirmed with <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy and powder X-ray diffraction techniques. The crystal structures of the compounds were characterized by single crystal X-ray diffraction (SCXRD) and their thermal properties were studied by Differential Scanning Calorimetry (DSC) analyses. The antibacterial properties of the title compounds against five bacterial strains were evaluated using Kirby–Bauer disk diffusion susceptibility test. The compounds crystallize in the monoclinic or orthorhombic crystal systems (space groups: <i>P</i>2<sub>1</sub>/<i>c</i>, <i>P</i>2<sub>1</sub>/<i>n,</i> or <i>P</i>2<sub>1</sub>2<sub>1</sub>2<sub>1</sub>) and their crystal structures are stabilized by a combination of intra- and intermolecular halogen bonding interactions, short contacts and π-π interactions. Above interactions, they contribute to the thermal stability and lack of phase transition effects up to 350 °C. Two of the compounds possess antibacterial effect against <i>E</i>. <i>coli</i> or <i>S</i>. <i>aureus</i> bacterial strains—similar or better than the kanamycin reference. |
| first_indexed | 2024-03-10T20:14:09Z |
| format | Article |
| id | doaj.art-1b1be6fb3d814ac596c30a30c6e2f899 |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-03-10T20:14:09Z |
| publishDate | 2020-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-1b1be6fb3d814ac596c30a30c6e2f8992023-11-19T22:42:38ZengMDPI AGCrystals2073-43522020-04-0110533910.3390/cryst10050339Novel Quaternary Ammonium Derivatives of 4-Pyrrolidino Pyridine: Synthesis, Structural, Thermal, and Antibacterial StudiesRusi Rusew0Vanya Kurteva1Boris Shivachev2Institute of Mineralogy and Crystallography “Acad. Ivan Kostov”, Bulgarian Academy of Sciences, Acad. G. Bonchev str., bl. 107, 1113 Sofia, BulgariaInstitute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev str., bl. 9, 1113 Sofia, BulgariaInstitute of Mineralogy and Crystallography “Acad. Ivan Kostov”, Bulgarian Academy of Sciences, Acad. G. Bonchev str., bl. 107, 1113 Sofia, BulgariaSix novel quaternary ammonium derivatives of 4-pyrrolidino pyridine were prepared and isolated via a facile one-pot synthesis and a simple purification procedure. The purity and the molecular structure of the 4-pyrrolidino pyridine derivatives were confirmed with <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy and powder X-ray diffraction techniques. The crystal structures of the compounds were characterized by single crystal X-ray diffraction (SCXRD) and their thermal properties were studied by Differential Scanning Calorimetry (DSC) analyses. The antibacterial properties of the title compounds against five bacterial strains were evaluated using Kirby–Bauer disk diffusion susceptibility test. The compounds crystallize in the monoclinic or orthorhombic crystal systems (space groups: <i>P</i>2<sub>1</sub>/<i>c</i>, <i>P</i>2<sub>1</sub>/<i>n,</i> or <i>P</i>2<sub>1</sub>2<sub>1</sub>2<sub>1</sub>) and their crystal structures are stabilized by a combination of intra- and intermolecular halogen bonding interactions, short contacts and π-π interactions. Above interactions, they contribute to the thermal stability and lack of phase transition effects up to 350 °C. Two of the compounds possess antibacterial effect against <i>E</i>. <i>coli</i> or <i>S</i>. <i>aureus</i> bacterial strains—similar or better than the kanamycin reference.https://www.mdpi.com/2073-4352/10/5/339single crystal XRDNMRpowder XRDDSCquaternary ammonium saltsantibacterial activity |
| spellingShingle | Rusi Rusew Vanya Kurteva Boris Shivachev Novel Quaternary Ammonium Derivatives of 4-Pyrrolidino Pyridine: Synthesis, Structural, Thermal, and Antibacterial Studies Crystals single crystal XRD NMR powder XRD DSC quaternary ammonium salts antibacterial activity |
| title | Novel Quaternary Ammonium Derivatives of 4-Pyrrolidino Pyridine: Synthesis, Structural, Thermal, and Antibacterial Studies |
| title_full | Novel Quaternary Ammonium Derivatives of 4-Pyrrolidino Pyridine: Synthesis, Structural, Thermal, and Antibacterial Studies |
| title_fullStr | Novel Quaternary Ammonium Derivatives of 4-Pyrrolidino Pyridine: Synthesis, Structural, Thermal, and Antibacterial Studies |
| title_full_unstemmed | Novel Quaternary Ammonium Derivatives of 4-Pyrrolidino Pyridine: Synthesis, Structural, Thermal, and Antibacterial Studies |
| title_short | Novel Quaternary Ammonium Derivatives of 4-Pyrrolidino Pyridine: Synthesis, Structural, Thermal, and Antibacterial Studies |
| title_sort | novel quaternary ammonium derivatives of 4 pyrrolidino pyridine synthesis structural thermal and antibacterial studies |
| topic | single crystal XRD NMR powder XRD DSC quaternary ammonium salts antibacterial activity |
| url | https://www.mdpi.com/2073-4352/10/5/339 |
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