Synthesis and evaluation of 6-methyl-3-phenylcoumarins as potent and selective MAO-B inhibitors

Matos, María Joäo; Viña, Dolores; Picciau, Carmen; Orallo, Francisco; Santana, Lourdes; Uriarte, Eugenio

doi:10.1016/j.bmcl.2009.07.039

Cited by 107 publications

(73 citation statements)

References 25 publications

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“…Perkin condensation [19,33,[37][38][39][40][41] were synthesized starting from the respective methoxy derivatives 1-5 by hydrolysis reaction, using hydriodic acid 57%.…”

Section: Materials and Methods For The Synthesis Of 3-(hydroxyphenyl)mentioning

confidence: 99%

Synthesis and electrochemical study of new 3-(hydroxyphenyl)benzo[f]coumarins

Matos

Janeiro

Santana

et al. 2014

Journal of Electroanalytical Chemistry

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“…Perkin condensation [19,33,[37][38][39][40][41] were synthesized starting from the respective methoxy derivatives 1-5 by hydrolysis reaction, using hydriodic acid 57%.…”

Section: Materials and Methods For The Synthesis Of 3-(hydroxyphenyl)mentioning

confidence: 99%

Synthesis and electrochemical study of new 3-(hydroxyphenyl)benzo[f]coumarins

Matos

Janeiro

Santana

et al. 2014

Journal of Electroanalytical Chemistry

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“…5,15 Flexible-ligand docking simulations were performed with AutoDock version 4.2. 17 X-ray crystallographic structure of MAO-B was retrieved from the Brookhaven protein data bank (1S2Q; http://www.rcsb.org/).…”

Section: Molecular Dockingmentioning

confidence: 99%

“…These two isoforms differ in their amino acid sequence, substrate specificity and sensitivity to selective inhibitors. 5 Selective MAO-A inhibitors such as clorgyline are effective antidepressant drugs, while selective MAO-B inhibitors have been exploited as anti-Parkinson agents. 6,7 MAO-B catalyzes the major catabolic pathway (oxidative deamination) of β-phenylethylamines such * For correspondence as dopamine in the brain.…”

Section: Introductionmentioning

confidence: 99%

Quantum chemical analysis of potential anti-Parkinson agents

et al. 2015

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Monoamine oxidases (MAOs) are amine oxidoreductase falvoenzymes that belong to the integral proteins of the outer mitochondrial membrane. MAO exists in two distinct isoforms; MAO-A and MAO-B. Inhibition of MAO-A and MAO-B is important for developing antidepressant and antiparkinson agents, respectively. In the light of the above explanations, detailed structure binding relationship studies on the intermolecular binding components of MAO-B complexes may unravel the way toward developing novel anti-Parkinson agents. In the present contribution, intermolecular binding pattern for a series of experimentally validated 3-arylcoumarin MAO-B inhibitors (1-9) have been elucidated via molecular docking and density functional theory (DFT) calculations. Intermolecular binding energy components could not be analyzed by docking and due to this limitation, quantum mechanical (QM) calculations including functional B3LYP in association with split valence basis set (Def2-SVP) were applied to estimate the ligand-residue binding energies in the MAO-B active site. Moreover; results were interpreted in terms of calculated polarization effects that were induced by individual amino acids of the MAO-B active site. The results of the present study provide an approach to pharmacophore-based modification within the 3-arylcoumarin scaffold for potent MAO-B 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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Synthesis and evaluation of 6-methyl-3-phenylcoumarins as potent and selective MAO-B inhibitors

Cited by 107 publications

References 25 publications

Synthesis and electrochemical study of new 3-(hydroxyphenyl)benzo[f]coumarins

Synthesis and electrochemical study of new 3-(hydroxyphenyl)benzo[f]coumarins

Quantum chemical analysis of potential anti-Parkinson agents

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

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