Unlocking the potential of trifluoromethyl pyrrole derivatives in chronic wounds management: rapid synthesis, structural insights, and potent antimicrobial activity
Using a one-pot, three-component approach, we synthesised 25 dihydropyrrol-2-one and two 5-oxo-2,5-dihydrofuran compounds, each featuring two trifluoromethyl groups. This method emphasises timeliness and cost-effectiveness, crucial in drug development. Structural verification was conducted using NMR...
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| Format: | Article |
| Language: | English |
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Taylor & Francis Group
2025-12-01
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| Series: | Journal of Enzyme Inhibition and Medicinal Chemistry |
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| Online Access: | https://www.tandfonline.com/doi/10.1080/14756366.2025.2513406 |
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| author | Rafaela Vrabie Mariana Pinteala Cristina M. Al-Matarneh Ioana C. Marinas Alina Nicolescu Sergiu Shova Mihaela Silion Mădălina-Diana Gaboreanu Mariana C. Chifiriuc |
| author_facet | Rafaela Vrabie Mariana Pinteala Cristina M. Al-Matarneh Ioana C. Marinas Alina Nicolescu Sergiu Shova Mihaela Silion Mădălina-Diana Gaboreanu Mariana C. Chifiriuc |
| author_sort | Rafaela Vrabie |
| collection | DOAJ |
| description | Using a one-pot, three-component approach, we synthesised 25 dihydropyrrol-2-one and two 5-oxo-2,5-dihydrofuran compounds, each featuring two trifluoromethyl groups. This method emphasises timeliness and cost-effectiveness, crucial in drug development. Structural verification was conducted using NMR, FT-IR, MALDI-MS, single-crystal, and powder XRD. The antibacterial and antifungal activities of these compounds were evaluated on yeasts (Candida sp.) and bacteria, including Gram-positive (Staphylococcus aureus, a significant opportunistic pathogen, being more susceptible than S. epidermidis) and Gram-negative strains. Compounds with o-OH and m′-NO2 groups exhibited superior activity, while those with p-OH and m-OMe groups showed slightly lower but still significant activity. For furan structures, Candida albicans displayed greater sensitivity than C. parapsilosis. Additionally, 13 compounds demonstrated haemolysis below 5%, indicating low toxicity. |
| format | Article |
| id | doaj-art-313291dd5d9345ca8ea494d358131f03 |
| institution | OA Journals |
| issn | 1475-6366 1475-6374 |
| language | English |
| publishDate | 2025-12-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Journal of Enzyme Inhibition and Medicinal Chemistry |
| spelling | doaj-art-313291dd5d9345ca8ea494d358131f032025-08-20T02:23:12ZengTaylor & Francis GroupJournal of Enzyme Inhibition and Medicinal Chemistry1475-63661475-63742025-12-0140110.1080/14756366.2025.2513406Unlocking the potential of trifluoromethyl pyrrole derivatives in chronic wounds management: rapid synthesis, structural insights, and potent antimicrobial activityRafaela Vrabie0Mariana Pinteala1Cristina M. Al-Matarneh2Ioana C. Marinas3Alina Nicolescu4Sergiu Shova5Mihaela Silion6Mădălina-Diana Gaboreanu7Mariana C. Chifiriuc8Center of Advanced Research in Bionanoconjugates and Biopolymers, “Petru Poni” Institute of Macromolecular Chemistry of Romanian Academy, Iasi, RomaniaCenter of Advanced Research in Bionanoconjugates and Biopolymers, “Petru Poni” Institute of Macromolecular Chemistry of Romanian Academy, Iasi, RomaniaCenter of Advanced Research in Bionanoconjugates and Biopolymers, “Petru Poni” Institute of Macromolecular Chemistry of Romanian Academy, Iasi, RomaniaResearch Institute of the University of Bucharest-ICUB, Bucharest, RomaniaNMR Laboratory, “Petru Poni” Institute of Macromolecular Chemistry of Romanian Academy, Iasi, RomaniaDepartment of Inorganic Polymers, “Petru Poni” Institute of Macromolecular Chemistry of Romanian Academy, Iasi, RomaniaPhysics of Polymers and Polymeric Materials Department, “Petru Poni” Institute of Macromolecular Chemistry, Iasi, RomaniaResearch Institute of the University of Bucharest-ICUB, Bucharest, RomaniaResearch Institute of the University of Bucharest-ICUB, Bucharest, RomaniaUsing a one-pot, three-component approach, we synthesised 25 dihydropyrrol-2-one and two 5-oxo-2,5-dihydrofuran compounds, each featuring two trifluoromethyl groups. This method emphasises timeliness and cost-effectiveness, crucial in drug development. Structural verification was conducted using NMR, FT-IR, MALDI-MS, single-crystal, and powder XRD. The antibacterial and antifungal activities of these compounds were evaluated on yeasts (Candida sp.) and bacteria, including Gram-positive (Staphylococcus aureus, a significant opportunistic pathogen, being more susceptible than S. epidermidis) and Gram-negative strains. Compounds with o-OH and m′-NO2 groups exhibited superior activity, while those with p-OH and m-OMe groups showed slightly lower but still significant activity. For furan structures, Candida albicans displayed greater sensitivity than C. parapsilosis. Additionally, 13 compounds demonstrated haemolysis below 5%, indicating low toxicity.https://www.tandfonline.com/doi/10.1080/14756366.2025.2513406Dihydro-pyrrol-2-oneDoebner-type synthesisantimicrobial activitytrifluoromethylchronic wounds |
| spellingShingle | Rafaela Vrabie Mariana Pinteala Cristina M. Al-Matarneh Ioana C. Marinas Alina Nicolescu Sergiu Shova Mihaela Silion Mădălina-Diana Gaboreanu Mariana C. Chifiriuc Unlocking the potential of trifluoromethyl pyrrole derivatives in chronic wounds management: rapid synthesis, structural insights, and potent antimicrobial activity Journal of Enzyme Inhibition and Medicinal Chemistry Dihydro-pyrrol-2-one Doebner-type synthesis antimicrobial activity trifluoromethyl chronic wounds |
| title | Unlocking the potential of trifluoromethyl pyrrole derivatives in chronic wounds management: rapid synthesis, structural insights, and potent antimicrobial activity |
| title_full | Unlocking the potential of trifluoromethyl pyrrole derivatives in chronic wounds management: rapid synthesis, structural insights, and potent antimicrobial activity |
| title_fullStr | Unlocking the potential of trifluoromethyl pyrrole derivatives in chronic wounds management: rapid synthesis, structural insights, and potent antimicrobial activity |
| title_full_unstemmed | Unlocking the potential of trifluoromethyl pyrrole derivatives in chronic wounds management: rapid synthesis, structural insights, and potent antimicrobial activity |
| title_short | Unlocking the potential of trifluoromethyl pyrrole derivatives in chronic wounds management: rapid synthesis, structural insights, and potent antimicrobial activity |
| title_sort | unlocking the potential of trifluoromethyl pyrrole derivatives in chronic wounds management rapid synthesis structural insights and potent antimicrobial activity |
| topic | Dihydro-pyrrol-2-one Doebner-type synthesis antimicrobial activity trifluoromethyl chronic wounds |
| url | https://www.tandfonline.com/doi/10.1080/14756366.2025.2513406 |
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