Academic Journal
Click Chemistry Approach to Derivatisation of Fluconazole.
| Τίτλος: | Click Chemistry Approach to Derivatisation of Fluconazole. |
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| Συγγραφείς: | Janowski M; Doctoral School, Medical University of Lublin, Chodzki 7, 20-093 Lublin, Poland., Demchuk OM; Faculty of Medicine, The John Paul II Catholic University of Lublin, Konstantynów 1J, 20-708 Lublin, Poland., Andrzejczuk S; Department of Pharmaceutical Microbiology, Faculty of Pharmacy, Medical University of Lublin, 1 Chodzki St., 20-093 Lublin, Poland., Pawlicka A; Department of Biochemistry, Faculty of Medicine, Medical University of Warsaw, Banacha St. 1, 02-097 Warsaw, Poland., Kosikowska U; Department of Pharmaceutical Microbiology, Faculty of Pharmacy, Medical University of Lublin, 1 Chodzki St., 20-093 Lublin, Poland., Struga M; Department of Biochemistry, Faculty of Medicine, Medical University of Warsaw, Banacha St. 1, 02-097 Warsaw, Poland., Feldo M; Department of Vascular Surgery, Medical University of Lublin, Staszica 11 St., 20-081 Lublin, Poland., Wujec M; Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Lublin, 4a Chodzki St., 20-093 Lublin, Poland. |
| Πηγή: | Molecules (Basel, Switzerland) [Molecules] 2026 Jul 22; Vol. 31 (14). Date of Electronic Publication: 2026 Jul 22. |
| Τύπος έκδοσης: | Journal Article |
| Γλώσσα: | English |
| Στοιχεία περιοδικού: | Publisher: MDPI Country of Publication: Switzerland NLM ID: 100964009 Publication Model: Electronic Cited Medium: Internet ISSN: 1420-3049 (Electronic) Linking ISSN: 14203049 NLM ISO Abbreviation: Molecules Subsets: MEDLINE |
| Imprint Name(s): | Original Publication: Basel, Switzerland : MDPI, c1995- |
| Ιατρικοί όροι (MeSH): | Click Chemistry*/methods , Antifungal Agents*/pharmacology , Antifungal Agents*/chemistry , Antifungal Agents*/chemical synthesis , Fluconazole*/pharmacology , Fluconazole*/chemistry , Fluconazole*/chemical synthesis , Candida*/drug effects, Azides/chemistry ; Copper/chemistry ; Alkynes/chemistry ; Microbial Sensitivity Tests ; Catalysis ; Molecular Structure ; Cycloaddition Reaction |
| Περίληψη: | The emergence of antimicrobial resistance necessitates the development of structurally novel agents with improved biological profiles. In this study, a series of new derivatives of fluconazole were designed, synthesized, and evaluated for antifungal activity. The synthetic approach involved esterification of hydroxyl group of fluconazole with an azide-group-containing benzoyl chloride, followed by copper-catalyzed azide-alkyne cycloaddition (CuAAC). The optimized catalytic system was based on a copper(I) catalyst generated from copper(II) palmitate and ascorbic acid. The transformations of the azide-containing derivatives were then performed. The obtained compounds were tested against reference strains of clinically relevant Candida spp., including C. albicans ATCC 10231, C. parapsilosis ATCC 22019, C. krusei ATCC 14243, C. auris CDC B11903, C. tropicalis ATCC 1369, C. glabrata ATCC 15126, and C. lusitaniae ATCC 3449. Some of the obtained derivatives showed very low toxicity in the MTT-based cell viability assay while maintaining high antifungal activity against selected strains. |
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| Grant Information: | 2019/33/B/NZ7/01608 National Science Centre |
| Contributed Indexing: | Keywords: 1,2,3-triazoles; 1,2,4-triazoles; CuAAC; antifungal agents; azide-alkyne Huisgen cycloaddition; click chemistry; copper catalysis; drug modification; fluconazole |
| Substance Nomenclature: | 0 (Antifungal Agents) 8VZV102JFY (Fluconazole) 0 (Azides) 789U1901C5 (Copper) 0 (Alkynes) |
| Entry Date(s): | Date Created: 20260728 Date Completed: 20260729 Latest Revision: 20260813 |
| Update Code: | 20260814 |
| PubMed Central ID: | PMC13415025 |
| DOI: | 10.3390/molecules31142545 |
| PMID: | 42513222 |
| Βάση Δεδομένων: | MEDLINE |
| ISSN: | 1420-3049 |
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| DOI: | 10.3390/molecules31142545 |