A novel synthesis of 3-aryl coumarins and evaluation of their antioxidant and lipoxygenase inhibitory activity

Roussaki, Marina; Kontogiorgis, Christos; Hadjipavlou‐Litina, Dimitra; Hamilakis, Stylianos; Detsi, Anastasia

doi:10.1016/j.bmcl.2010.05.022

Cited by 148 publications

(71 citation statements)

References 26 publications

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“…Although various methods have been reported for this reaction, they suffer from disadvantages such as long reaction time, using expensive and/or nonstable catalyst and using heterogeneous catalysts [15][16][17][18][19][20][21]. There is widespread interest in the synthesis of new coumarin derivatives, because of their applications in organic synthesis, biology, medicine, perfumes and cosmetics fields [22,23]. Also some of the coumarin derivatives are known as antioxidant compounds, due to their radical scavenging properties [24].…”

Section: Introductionmentioning

confidence: 99%

Magnetic nanoparticles functionalized ethane sulfonic acid (MNESA): as an efficient catalyst in the synthesis of coumarin derivatives using Pechmann condensation under mild condition

2016

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This paper reports an efficient heterogeneous catalyst based on sulfonic acid functionalization of magnetic nanoparticles. This new catalyst was prepared using the reaction between magnetic nanoparticles and sodium 2-bromoethane-1-sulfonate. Magnetic nanoparticles functionalized ethane sulfonic acid (MNESA) was found as efficient catalyst for the synthesis of coumarin derivatives using Pechmann condensation under mild condition. This reaction was catalyzed by MNESA under solvent-free condition at 90°C, to give the corresponding products in excellent yields. The catalyst is easily separated from the reaction condition and can be reused for several times with consistence in the activity.

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Section: Introductionmentioning

confidence: 99%

Magnetic nanoparticles functionalized ethane sulfonic acid (MNESA): as an efficient catalyst in the synthesis of coumarin derivatives using Pechmann condensation under mild condition

2016

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“…Umbelliferone also known as 7-hydroxy coumarin is a natural product widely distributed in many familiar plants Apiaceae, Asteraceae, Hydrangeaceae and Acanthaceae. Coumarin derivatives are of great interest due to their diverse structural features and versatile biological properties, such as anti-inflammatory, antioxidant, vasorelaxant, cytotoxic, anti-HIV, antitubercular and antimicrobial [17][18][19][20][21][22] . Coumarin derivatives have been synthesized and extensively studied for their biological response, but the tyrosinase inhibitor activities of this kind of compounds have hardly ever appeared in the literature.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and bioevaluation of novel umbelliferone analogues as potential mushroom tyrosinase inhibitors

Ashraf

Rafiq

Seo

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of umbelliferone analogues were synthesized and their inhibitory effects on the DPPH and mushroom tyrosinase were evaluated. The results showed that some of the synthesized compounds exhibited significant mushroom tyrosinase inhibitory activities. Especially, 2-oxo-2-[(2-oxo-2H-chromen-7-yl)oxy]ethyl-2,4-dihydroxybenzoate (4e) bearing 2,4-dihydroxy substituted phenyl ring exhibited the most potent tyrosinase inhibitory activity with IC 50 value 8.96 mM and IC 50 value of kojic acid is 16.69. The inhibition mechanism analyzed by LineweaverBurk plots revealed that the type of inhibition of compound 4e on tyrosinase was noncompetitive. The docking study against tyrosinase enzyme was also performed to determine the binding affinity of the compounds. The compounds 4c and 4e showed the highest binding affinity with active binding site of tyrosinase. The initial structure activity relationships (SARs) analysis suggested that further development of such compounds might be of interest. The statistics of our results endorses that compounds 4c and 4e may serve as a structural template for the design and development of novel tyrosinase inhibitors.

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“…[1,2] These heterocyclic compounds have already been previously described as anticancer, antiviral, anti-inflammatory, antimicrobial, enzymatic inhibitory and antioxidant agents. [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] Taking in account the versatility of the coumarin moiety one can thoroughly modify it to best serve one purposes. In this work, our group fused two other classes of natural products onto the coumarin skeleton, the chalcones (figure 1 -A) and the resveratrol derivatives ( figure 1 -B).…”

Section: Introductionmentioning

confidence: 99%

Structural Modifications on Natural-based Products: Synthetic Strategies and Biological Applications

Fonseca

Matos

Vázquez-Rodríguez

et al. 2014

Proceedings of the 18th International Electronic Conference on Synthetic Organic Chemistry

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Coumarins are a class of heterocyclic compounds present in a significant quantity in several plants. The simplest coumarin, a benzene ring fused with a pyran-2-one heterocycle, was first discovered in the 19 th century and since then, due to the synthetic accessibility and the biological properties of its derivatives, has been playing an important role in the Medicinal Chemistry field. In fact, coumarins have been previously described as anticancer, antiviral, anti-inflammatory, antimicrobial, enzymatic inhibitory and antioxidant agents.Another two interesting compounds found widely in nature are resveratrol derivatives and chalcones. Both families of compounds are known for having remarkable antioxidant activity, cardio-and neuroprotective effects, among other relevant biological properties. Therefore, we devised several synthetic strategies to incorporate these natural products in one compound, combining their potential as promising agents for the treatment of several illnesses.In our group, we have already synthesised multiple novel compounds incorporating into the coumarin scaffold the resveratrol or chalcones moieties with remarkable activities towards different pharmacological targets. In this work, we continue exploiting this strategy by incorporating different linkers at coumarin position 3, thus giving us a wide range of possibilities for new compounds.

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A novel synthesis of 3-aryl coumarins and evaluation of their antioxidant and lipoxygenase inhibitory activity

Cited by 148 publications

References 26 publications

Magnetic nanoparticles functionalized ethane sulfonic acid (MNESA): as an efficient catalyst in the synthesis of coumarin derivatives using Pechmann condensation under mild condition

Magnetic nanoparticles functionalized ethane sulfonic acid (MNESA): as an efficient catalyst in the synthesis of coumarin derivatives using Pechmann condensation under mild condition

Design, synthesis and bioevaluation of novel umbelliferone analogues as potential mushroom tyrosinase inhibitors

Structural Modifications on Natural-based Products: Synthetic Strategies and Biological Applications

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