Transition metal-catalyzed synthesis of new 3-substituted coumarin derivatives as antibacterial and cytostatic agents
| Autor: | Domagoj Drenjančević, Andrijana Meščić Macan, Tatjana Gazivoda Kraljević, Ivana Sokol, Mateja Toma, Sandra Liekens, Mia Krnić, Silvana Raić-Malić |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
Methicillin-Resistant Staphylococcus aureus
1 2 3-Triazole Cytostatic agents Sonogashira coupling Microbial Sensitivity Tests 01 natural sciences Catalysis 03 medical and health sciences chemistry.chemical_compound Transition metal Coumarins Drug Discovery Transition Elements Humans heterocyclic compounds 030304 developmental biology Pharmacology 0303 health sciences Molecular Structure 010405 organic chemistry Chemistry Coumarin Cytostatic Agents Combinatorial chemistry 1 2 3-triazole 3-substituted coumarin antibacterial antitumor click reaction coumarin Suzuki-Miyaura coupling 3. Good health 0104 chemical sciences Anti-Bacterial Agents Vancomycin-Resistant Staphylococcus aureus Click chemistry Molecular Medicine |
| Zdroj: | Future medicinal chemistry. 13(21) |
| ISSN: | 1756-8927 |
| Popis: | Aim: The aim of this study was to synthesize new coumarin-based compounds and evaluate their antibacterial and antitumor potential. Results: Using transition metal-catalyzed reactions, a series of 7-hydroxycoumarin derivatives were synthesized with aliphatic and aryl moiety attached directly at C-3 of the coumarin ring and through the ethynyl or 1,2,3-triazole linker. The 3-substituted coumarin derivative bearing bistrifluoromethylphenyl at the C-4 position of 1,2,3-triazole (33) showed strong and selective antiproliferative activity against cervical carcinoma cells. The 7-hydroxy-4-methylcoumarin with a phenyl ring directly attached to coumarin at C-3 (10) showed good potency against the methicillin-resistant Staphylococcus aureus and vancomycin-resistant strains. Conclusion: The most active coumarin derivatives owe their antiproliferative potential to the 3,5-ditrifluoromethylphenyl substituent (in 33) and antibacterial activity to the aromatic moiety (in 10); their structure can be optimized further for improved effect. |
| Databáze: | OpenAIRE |
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