A new series of 3-phenylcoumarins as potent and selective MAO-B inhibitors

Matos, María Joäo; Viña, Dolores; Quezada, Elías; Picciau, Carmen; Delogu, Giovanna; Orallo, Francisco; Santana, Lourdes; Uriarte, Eugenio

doi:10.1016/j.bmcl.2009.04.085

Cited by 132 publications

(85 citation statements)

References 26 publications

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“…In particular, it seems that the presence of an aryl or heteroaryl moiety on the 3-position of the coumarinic system induces specific activities. 16 We have recently reported a particularly useful, easy and concise synthesis of diversified 3-aryl coumarin using Heck coupling reactions between coumarin and arylhalides. 17 One can anticipate that the extension of the p-delocalized system will lead to compounds showing a more promising fluorescent behavior.…”

Section: Introductionmentioning

confidence: 99%

An efficient methodology for the synthesis of 3-styryl coumarins

Martins¹,

Branco²,

Pereira³

2012

J. Braz. Chem. Soc.

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Foi desenvolvida a arilação de Heck, regiosseletiva e altamente eficiente, de 3-vinil-6,7-dimetoxicumarina, para a obtenção de 3-estiril cumarinas com bons a excelentes rendimentos. O aumento da conjugação nos produtos sintetizados reflete na absorvância, revelando todos desvios batocrômicos pronunciados e efeitos hipercrômicos.Regioselective and highly efficient Heck arylation of 3-vinyl-6,7-dimethoxycoumarin has been developed to afford 3-styryl coumarins in good to very high yields. The increase in conjugation reflects on the absorbance of the synthesized compounds revealing all pronounced bathochromic shifts and hyperchromic effects.

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Section: Introductionmentioning

confidence: 99%

An efficient methodology for the synthesis of 3-styryl coumarins

Martins¹,

Branco²,

Pereira³

2012

J. Braz. Chem. Soc.

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“…Privileged structures, such as indoles, arylpiperazines, biphenyls and benzopyranes are currently ascribed as helpful approaches. In fact, different families of nitrogen and oxygen heterocycles, such as pyrazoles, hydrazinylthiazoles, xanthones, coumarins or chromones have been extensively used as scaffolds in medicinal chemistry programs for the search of novel MAO-B inhibitors [51][52][53][54][55][56][57]. There are a large number of studies on the identification of novel potent and selective MAO inhibitors that could serve as potential lead molecules for drug discovery.…”

Section: Drug Discovery and Development Of Mao-b Inhibitorsmentioning

confidence: 99%

Parkinson's Disease Management. Part II- Discovery of MAO-B Inhibitors Based on Nitrogen Heterocycles and Analogues

Reis¹,

Encarnacao²,

Gaspar³

et al. 2012

Current Topics in Medicinal Chemistry

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Parkinson's disease (PD) is a neurodegenerative disorder mainly characterized by a progressive neurodegeneration of the dopaminergic neurons. The available pharmacological therapy for PD aims to stop the progress of symptoms, reduce disability, slowing the neurodegenerative process and/or preventing long-term complications along the therapy. The main strategic developments that have led to progress in the medical management of PD have focused on improvements in dopaminergic therapies. Despite all the recent research, there are only a few classes of drugs approved for the treatment of motor related symptoms of PD which primarily act on the dopaminergic neurons system: L-dopa, dopamine agonists, monoamine oxidase-B (MAO-B) and catechol-O-methyl transferase (COMT) inhibitors. Anticholinergic drugs and glutamate antagonists are also available but are not commonly used in routine practice. As no effective therapeutic strategy has yet been attended, other solutions must be investigated. Privileged structures, such as indoles, arylpiperazines, biphenyls and benzopyranes are currently ascribed as helpful approaches. Different families of nitrogen and oxygen heterocycles, such as pyrazoles, hydrazinylthiazoles, xanthones, coumarins or chromones have also been extensively used as scaffolds in medicinal chemistry programs for searching novel MAO-B inhibitors. Nitrogen derivatives play a key role in this subject with several studies pointing out hydrazines, thiazoles or indoles as important scaffolds for the development of novel MAO-B inhibitors. This review comprises an overview of the state of the art on the actual pharmacological therapy for PD followed by a specific focus on the discovery and development of nitrogen-based heterocyclic compounds analogues as promising MAO-B inhibitors.

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“…[15][16][17][18] Furthermore, various arylcoumarin derivatives, e.g., 3-arylcoumarin 7 (IC 50 = 2.79 AE 0.19 mM) and 8 (IC 50 = 8.98 AE 1.42 nM) were recently reported to be the most effective inhibitors of MAO-B, an isoenzyme of MAO ( Figure 1). [19,20] In addition, the motif of 3-arylated dihydroisocoumarins, for example, thunberginol G (9), a herbal medical ingredient, [21] is prevalent in nature ( Figure 2). In comparison to this, the corresponding dihydrocoumarins were investigated far less: A notable exception is calomelanol G (10) a flavanone also containing a 4-aryldihydrocoumarin motif.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 3‐Arylated 3,4‐Dihydrocoumarins: Combining Continuous Flow Hydrogenation with Laccase‐Catalysed Oxidation

Suljić

Pietruszka

2014

Adv Synth Catal

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A convenient arylation of diverse 3,4-dihydrocoumarins with a number of catechols is described leading to a new class of compounds. As key step, a laccase-catalysed oxidation/Michael addition sequence is applied using commercially available laccase from Agaricus bisporus. 3,4-Dihydrocoumarins were obtained in a rapid and facile two-step sequence starting from salicylaldehydes: The corresponding coumarins were synthesised through a Knoevenagel condensation in up to 83% yield followed by a quantitative reduction performed in a flow system. Combining the reductive flow reaction with the laccase-catalysed arylation also led to successful consecutive one-pot approaches. Overall, the enzyme-catalysed arylations were carried out with yields ranging from 63 to 94%.

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A new series of 3-phenylcoumarins as potent and selective MAO-B inhibitors

Cited by 132 publications

References 26 publications

An efficient methodology for the synthesis of 3-styryl coumarins

An efficient methodology for the synthesis of 3-styryl coumarins

Parkinson's Disease Management. Part II- Discovery of MAO-B Inhibitors Based on Nitrogen Heterocycles and Analogues

Synthesis of 3‐Arylated 3,4‐Dihydrocoumarins: Combining Continuous Flow Hydrogenation with Laccase‐Catalysed Oxidation

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