Novel 1, 2, 3-triazolic compounds derived from cytosine: Synthesis, spectroscopic characterization, in vitro antimicrobial activity and molecular docking studies
The development of novel antimicrobial drugs is crucial due to the increasing problem of antibiotic resistance. A new series of 1,4-disubstituted-1,2,3-triazole derivatives containing a cytosine moiety (3a, 3b, 3c and 3d) were synthesized using 1,3-dipolar cycloaddition in a mixture of ethanol and w...
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| Format: | Article |
| Language: | English |
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Elsevier
2024-01-01
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| Series: | Results in Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715624001061 |
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| author | Mouad Lahyaoui Riham Sghyar Khadija Benamar Mouad Filali Kawtar Fikri-Benbrahim Badr Eddine Kartah Ahmed Mazzah Youssef Kandri Rodi Nada Kheira Sebbar |
| author_facet | Mouad Lahyaoui Riham Sghyar Khadija Benamar Mouad Filali Kawtar Fikri-Benbrahim Badr Eddine Kartah Ahmed Mazzah Youssef Kandri Rodi Nada Kheira Sebbar |
| author_sort | Mouad Lahyaoui |
| collection | DOAJ |
| description | The development of novel antimicrobial drugs is crucial due to the increasing problem of antibiotic resistance. A new series of 1,4-disubstituted-1,2,3-triazole derivatives containing a cytosine moiety (3a, 3b, 3c and 3d) were synthesized using 1,3-dipolar cycloaddition in a mixture of ethanol and water under Cu(I)-catalyzed with N-alkyl: 1-(prop-2-ynyl)-4-amino-2-oxopyrimidine 2 as dipolarophiles and azide derivatives (sucre-azoture) as dipoles. The desired products were obtained in good yields by reacting with a catalytic amount of copper (II) sulfate and sodium ascorbate. The structure of these compounds was analyzed and characterized using spectroscopic measurements such as 1H NMR, 13C NMR, and mass spectroscopy. Encouragingly, all cycloaddition molecules exhibited promising activity against various bacterial strains including Staphylococcus aureus and Escherichia coli. The crystal structure modeling of protein 7AZ5 demonstrated strong binding affinities through hydrogen bonds with these molecules. The cycloaddition compounds displayed the highest binding energies in terms of antimicrobial efficacy. This suggests that these substances could serve as an effective model for the development and production of new and potent antimicrobial agents. |
| first_indexed | 2024-04-25T01:22:20Z |
| format | Article |
| id | doaj.art-4a88d6e6f7944054903544831ded57e1 |
| institution | Directory Open Access Journal |
| issn | 2211-7156 |
| language | English |
| last_indexed | 2024-04-25T01:22:20Z |
| publishDate | 2024-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj.art-4a88d6e6f7944054903544831ded57e12024-03-09T09:24:55ZengElsevierResults in Chemistry2211-71562024-01-017101410Novel 1, 2, 3-triazolic compounds derived from cytosine: Synthesis, spectroscopic characterization, in vitro antimicrobial activity and molecular docking studiesMouad Lahyaoui0Riham Sghyar1Khadija Benamar2Mouad Filali3Kawtar Fikri-Benbrahim4Badr Eddine Kartah5Ahmed Mazzah6Youssef Kandri Rodi7Nada Kheira Sebbar8Laboratory of Applied Organic Chemistry, Faculty of Science and Techniques, Sidi Mohamed Ben Abdellah University, B.P. 2202, Route d 'Imouzzer, Fez 30050, MoroccoLaboratory of Applied Organic Chemistry, Faculty of Science and Techniques, Sidi Mohamed Ben Abdellah University, B.P. 2202, Route d 'Imouzzer, Fez 30050, MoroccoLaboratory of Microbial Biotechnology and Bioactive Molecules, Faculty of Science and Techniques, Sidi Mohamed Ben Abdellah University, B.P. 2202, Route d 'Imouzzer, Fez 30050, MoroccoLaboratory of Applied Organic Chemistry, Faculty of Science and Techniques, Sidi Mohamed Ben Abdellah University, B.P. 2202, Route d 'Imouzzer, Fez 30050, MoroccoLaboratory of Microbial Biotechnology and Bioactive Molecules, Faculty of Science and Techniques, Sidi Mohamed Ben Abdellah University, B.P. 2202, Route d 'Imouzzer, Fez 30050, MoroccoLaboratory of Plant Chemistry, Organic and Bioorganic Synthesis, Faculty of Sciences, Mohammed V University in Rabat, 4 Avenue Ibn Battouta B.P. 1014 RP, MoroccoUniversity of Lille, CNRS, USR 3290, MSAP, Miniaturization for Synthesis, Analysis and Proteomics, F-59000 Lille, FranceLaboratory of Applied Organic Chemistry, Faculty of Science and Techniques, Sidi Mohamed Ben Abdellah University, B.P. 2202, Route d 'Imouzzer, Fez 30050, MoroccoLaboratory of Plant Chemistry, Organic and Bioorganic Synthesis, Faculty of Sciences, Mohammed V University in Rabat, 4 Avenue Ibn Battouta B.P. 1014 RP, Morocco; Laboratory of Organic and Physical Chemistry, Applied Bioorganic Chemistry Team, Faculty of Sciences, Ibnou Zohr University, Agadir, Morocco; Corresponding author at: Laboratory of Organic and Physical Chemistry, Applied Bioorganic Chemistry Team, Faculty of Sciences, Ibnou Zohr University, Agadir, Morocco.The development of novel antimicrobial drugs is crucial due to the increasing problem of antibiotic resistance. A new series of 1,4-disubstituted-1,2,3-triazole derivatives containing a cytosine moiety (3a, 3b, 3c and 3d) were synthesized using 1,3-dipolar cycloaddition in a mixture of ethanol and water under Cu(I)-catalyzed with N-alkyl: 1-(prop-2-ynyl)-4-amino-2-oxopyrimidine 2 as dipolarophiles and azide derivatives (sucre-azoture) as dipoles. The desired products were obtained in good yields by reacting with a catalytic amount of copper (II) sulfate and sodium ascorbate. The structure of these compounds was analyzed and characterized using spectroscopic measurements such as 1H NMR, 13C NMR, and mass spectroscopy. Encouragingly, all cycloaddition molecules exhibited promising activity against various bacterial strains including Staphylococcus aureus and Escherichia coli. The crystal structure modeling of protein 7AZ5 demonstrated strong binding affinities through hydrogen bonds with these molecules. The cycloaddition compounds displayed the highest binding energies in terms of antimicrobial efficacy. This suggests that these substances could serve as an effective model for the development and production of new and potent antimicrobial agents.http://www.sciencedirect.com/science/article/pii/S2211715624001061CycloadditionTriazolesCytosineAntimicrobial activityDocking studies |
| spellingShingle | Mouad Lahyaoui Riham Sghyar Khadija Benamar Mouad Filali Kawtar Fikri-Benbrahim Badr Eddine Kartah Ahmed Mazzah Youssef Kandri Rodi Nada Kheira Sebbar Novel 1, 2, 3-triazolic compounds derived from cytosine: Synthesis, spectroscopic characterization, in vitro antimicrobial activity and molecular docking studies Results in Chemistry Cycloaddition Triazoles Cytosine Antimicrobial activity Docking studies |
| title | Novel 1, 2, 3-triazolic compounds derived from cytosine: Synthesis, spectroscopic characterization, in vitro antimicrobial activity and molecular docking studies |
| title_full | Novel 1, 2, 3-triazolic compounds derived from cytosine: Synthesis, spectroscopic characterization, in vitro antimicrobial activity and molecular docking studies |
| title_fullStr | Novel 1, 2, 3-triazolic compounds derived from cytosine: Synthesis, spectroscopic characterization, in vitro antimicrobial activity and molecular docking studies |
| title_full_unstemmed | Novel 1, 2, 3-triazolic compounds derived from cytosine: Synthesis, spectroscopic characterization, in vitro antimicrobial activity and molecular docking studies |
| title_short | Novel 1, 2, 3-triazolic compounds derived from cytosine: Synthesis, spectroscopic characterization, in vitro antimicrobial activity and molecular docking studies |
| title_sort | novel 1 2 3 triazolic compounds derived from cytosine synthesis spectroscopic characterization in vitro antimicrobial activity and molecular docking studies |
| topic | Cycloaddition Triazoles Cytosine Antimicrobial activity Docking studies |
| url | http://www.sciencedirect.com/science/article/pii/S2211715624001061 |
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