Syntheses of Minutuminolate and Related Coumarin Natural Products and Evaluation of Their TNF-α Inhibitory Activities.
| Autor: | Choo MZY; Department of Pharmacy, National University of Singapore, 18 Science Drive 4, Singapore, 117543, Singapore., Khaw LWT; Department of Pharmacy, National University of Singapore, 18 Science Drive 4, Singapore, 117543, Singapore., Chai CLL; Department of Pharmacy, National University of Singapore, 18 Science Drive 4, Singapore, 117543, Singapore. |
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| Jazyk: | angličtina |
| Zdroj: | ACS omega [ACS Omega] 2023 Oct 23; Vol. 8 (44), pp. 41785-41791. Date of Electronic Publication: 2023 Oct 23 (Print Publication: 2023). |
| DOI: | 10.1021/acsomega.3c06361 |
| Abstrakt: | The concise syntheses of the coumarin natural product, minutuminolate ( 1 ), and its related natural products, 7-methoxy-8-(2-acetoxy-3-methyl-1-oxobut-2-enyl) coumarin ( 2 ) and muralatin I ( 3 ), were accomplished for the first time in 4-5 steps from the commercially available umbelliferone. The key step involves a palladium-catalyzed oxidative rearrangement reaction to assemble the α-acyloxyenone moiety in 1 and 2 . The incorporation of this functionality enables the successful synthesis of coumarin 3 through an acidic hydrolysis reaction. The anti-inflammatory activities of the compounds were also evaluated against tumor necrosis factor-alpha production in lipopolysaccharides-stimulated RAW264.7 cells. Our developed synthetic route will facilitate the development of analogues and derivatives of 1 - 3 with potent anti-inflammatory activities. Competing Interests: The authors declare no competing financial interest. (© 2023 The Authors. Published by American Chemical Society.) |
| Databáze: | MEDLINE |
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