Synthesis, Antibacterial Properties and Molecular Docking Studies of Nitrogen Substituted 9-(((4X-But-2-ynyloxy)methyl)-1,2,3-triazolyl)–Cinchona Alkaloid Conjugates; Molecules; Vol. 30, iss. 22
| Parent link: | Molecules.— .— Basel: MDPI AG Vol. 30, iss. 22.— 2025.— Article number 4352, 29 p. |
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| מחברים אחרים: | , , , , , , , , , , , |
| סיכום: | Title screen The year 2024 marked the 80th anniversary of Woodward’s total synthesis of quinine. Quinine is a natural alkaloid from the bark of the cinchona tree that has been used for years as an antimalarial drug. The antibacterial effect of quinine salts has also been regarded. With this in mind, a series of original 9-deoxycinchone alkaloid derivatives bearing a dialkylamino- or heterocyclic moiety at the 4 position of the 9-(((4-X-but-2-ynyloxy)methyl)-1,2,3-triazolyl)-substituent was synthesized. The copper-catalyzed three-component A3-coupling reaction of 9-(((4-prop-2-ynyloxy)methyl)-1,2,3-triazolyl)- substituted cinchona alkaloid derivatives with secondary amines and formaldehyde was the main route of synthesis. The present study attempted to examine the antibacterial properties of 9-substituted 9-desoxyquinine-derived compounds and their antibacterial activity against pathogenic bacterial strains, e.g., Staphylococcus aureus, Bacillus subtillis, Bacillus cereus, and Escherichia coli. The difference in the antibacterial activity profile of diastereoisomeric 9-(((4-X-but-2-ynyloxy)methyl)-1,2,3-triazolyl)-substituted derivatives of cinchona alkaloids indicated the importance of the nature of nitrogen substituents in the molecules. In a concentration-dependent pattern, (9R)- and (9S)- (((4-asocan-1yl)-but-2-ynyl-oxy)methyl)-1,2,3-triazolyl)-substituted compounds demonstrated considerable biofilm-inhibitory efficacy against the S. aureus bacterial strain. A detailed study of the molecular interactions with the targeted protein MurB was performed using docking simulations, and the obtained results are quite promising Текстовый файл |
| שפה: | אנגלית |
| יצא לאור: |
2025
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| נושאים: | |
| גישה מקוונת: | https://doi.org/10.3390/molecules30224352 |
| פורמט: | אלקטרוני Book Chapter |
| KOHA link: | https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=684391 |
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| 200 | 1 | |a Synthesis, Antibacterial Properties and Molecular Docking Studies of Nitrogen Substituted 9-(((4X-But-2-ynyloxy)methyl)-1,2,3-triazolyl)–Cinchona Alkaloid Conjugates |f Gulim K. Mukusheva, Nurizat N. Toigambekova, Victor A. Savelyev [et al.] | |
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| 330 | |a The year 2024 marked the 80th anniversary of Woodward’s total synthesis of quinine. Quinine is a natural alkaloid from the bark of the cinchona tree that has been used for years as an antimalarial drug. The antibacterial effect of quinine salts has also been regarded. With this in mind, a series of original 9-deoxycinchone alkaloid derivatives bearing a dialkylamino- or heterocyclic moiety at the 4 position of the 9-(((4-X-but-2-ynyloxy)methyl)-1,2,3-triazolyl)-substituent was synthesized. The copper-catalyzed three-component A3-coupling reaction of 9-(((4-prop-2-ynyloxy)methyl)-1,2,3-triazolyl)- substituted cinchona alkaloid derivatives with secondary amines and formaldehyde was the main route of synthesis. The present study attempted to examine the antibacterial properties of 9-substituted 9-desoxyquinine-derived compounds and their antibacterial activity against pathogenic bacterial strains, e.g., Staphylococcus aureus, Bacillus subtillis, Bacillus cereus, and Escherichia coli. The difference in the antibacterial activity profile of diastereoisomeric 9-(((4-X-but-2-ynyloxy)methyl)-1,2,3-triazolyl)-substituted derivatives of cinchona alkaloids indicated the importance of the nature of nitrogen substituents in the molecules. In a concentration-dependent pattern, (9R)- and (9S)- (((4-asocan-1yl)-but-2-ynyl-oxy)methyl)-1,2,3-triazolyl)-substituted compounds demonstrated considerable biofilm-inhibitory efficacy against the S. aureus bacterial strain. A detailed study of the molecular interactions with the targeted protein MurB was performed using docking simulations, and the obtained results are quite promising | ||
| 336 | |a Текстовый файл | ||
| 461 | 1 | |t Molecules |c Basel |n MDPI AG | |
| 463 | 1 | |t Vol. 30, iss. 22 |v Article number 4352, 29 p. |d 2025 | |
| 610 | 1 | |a cinchona alkaloids; quinine | |
| 610 | 1 | |a triazoles | |
| 610 | 1 | |a A3-coupling reactions | |
| 610 | 1 | |a antibacterial activity | |
| 610 | 1 | |a bacterial biofilms | |
| 610 | 1 | |a molecular docking study | |
| 610 | 1 | |a электронный ресурс | |
| 610 | 1 | |a труды учёных ТПУ | |
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| 701 | 1 | |a Toigambekova |b N. N. |g Nurizat | |
| 701 | 1 | |a Savelyev |b V. A. |g Victor | |
| 701 | 1 | |a Khlebnikov |b A. I. |c Chemist |c Professor of Tomsk Polytechnic University |f 1963- |g Andrey Ivanovich |9 17500 | |
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| 701 | 1 | |a Evstropov |b A. N. |g Alexander | |
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