Inhibition of monoamine oxidase by indole and benzofuran derivatives

Prins, Louis H.A.; Petzer, Jacobus P.; Malan, Sarel F.

doi:10.1016/j.ejmech.2010.07.005

Cited by 61 publications

(35 citation statements)

References 39 publications

(40 reference statements)

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“…These results suggest that the compounds 10b and 10e are reversible inhibitors of hMAO-B and have considerable advantages compared to irreversible inhibitors which may show safety issues and pharmacological side effects. 12,27 This data disagree with that obtained by …”

Section: Reversibility Of Mao-bcontrasting

confidence: 85%

Synthesis of a series of unsaturated ketone derivatives as selective and reversible monoamine oxidase inhibitors

Choi

Jang

Cho

et al. 2015

Bioorganic & Medicinal Chemistry

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Section: Reversibility Of Mao-bcontrasting

confidence: 85%

Synthesis of a series of unsaturated ketone derivatives as selective and reversible monoamine oxidase inhibitors

Choi

Jang

Cho

et al. 2015

Bioorganic & Medicinal Chemistry

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“…Concentration measurements of 4-hydroxyquinoline were conveniently carried out by fluorescence spectrophotometry (excitation wavelength of 310; emission wavelength of 400 nm) since none of the inhibitors investigated in this study fluoresced at these excitation/emission wavelengths or quenched the fluorescence of 4-hydroxyquinoline at the inhibitor concentrations used. 35 The inhibition potencies of the test inhibitors were calculated from the experimentally obtained sigmoidal dose-response curves and expressed as the IC 50 values (Fig. 3).…”

Section: Mao Inhibition Studiesmentioning

confidence: 99%

Inhibition of monoamine oxidase by C5-substituted phthalimide analogues

Manley-King

Bergh

Petzer

2011

Bioorganic & Medicinal Chemistry

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“…Selective MAO-A inhibitors are used as anti-depressant and anti-anxiety drugs whereas selective MAO-B inhibitors are used to treat Parkinson's disease. [3][4][5] Recently, several research groups have reported chromone derivatives substituted at different positions of the chromone ring and their inhibitory effects towards MAO-A and MAO-B.2,6-12) These reports suggested that structural changes induced by the substitutions on the chromone ring can increase the biological activity of the compound.Azoles such as pyrrole , 13) pyrazole , 14) indole 15) and benzazole 16) containing compounds have also been reported as potent MAO inhibitors. We therefore proposed that chromones bearing an azole moiety should display interesting monoamine oxidase inhibitory activities.…”

mentioning

confidence: 99%

“…Azoles such as pyrrole, 13) pyrazole, 14) indole 15) and benzazole 16) containing compounds have also been reported as potent MAO inhibitors. We therefore proposed that chromones bearing an azole moiety should display interesting monoamine oxidase inhibitory activities.…”

mentioning

confidence: 99%

2-Azolylchromone Derivatives as Potent and Selective Inhibitors of Monoamine Oxidases A and B

Takao

Saito

Chikuda

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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A series of 2-azolylchromone derivatives were synthesized and their monoamine oxidase (MAO) A and B inhibitory activities were evaluated. Of the synthesized compounds, compounds 1b, 2b, 4a-c, 5b and 7b showed potent inhibitory activities against MAO-A (IC 50 values, 1b: 0.32 µM; 2b: 0.14 µM; 4a: 0.11 µM; 4b: 0.023 µM; 4c: 0.15 µM; 5b: 0.59 µM; 7b: 0.19 µM) and 4a, c, 5a, c, 6c and 8c for MAO-B (IC 50 values, 4a: 0.028 µM; 4c: 0.019 µM; 5a: 0.73 µM; 5c: 0.28 µM; 6c: 0.28 µM; 8c: 0.27 µM). These data suggest that 6-methoxy substitution favors MAO-A inhibition and 7-methoxy substitution favors MAO-B inhibition. In addition, compound 4b was the most potent inhibitor for MAO-A, and compound 4c for MAO-B. This is the first report identifying 2-azolylchromone derivatives as potent monoamine oxidase inhibitors. These results suggest that the 2-triazolylchromone structure may be a useful scaffold for the design and development of novel monoamine oxidase inhibitors, as evidenced by the activities of 4a-c and 5a-c.Key words 2-azolylchromone; monoamine oxidase A; monoamine oxidase B; inhibitor; structure-activity relationship; 2-triazolylchromone 4H-1-Benzopyran-4-ones (chromones) are an important class of oxygenated heterocyclic compounds that have attracted the attention of organic chemists and biochemists due to their biological activities. The chromone core structure is found in flavones and isoflavones, which are secondary metabolites that are ubiquitous in nature and especially in the plant kingdom, and are present in notable amounts in several species of plants. The chromone scaffold is the pharmacophore of a large number of bioactive molecules of either natural or synthetic origin. The biological effects of these bioactive molecules include anti-inflammatory, anti-tumor and anti-microbial activities, and inhibitory activities towards cyclooxygenases, kinases, phosphatases, aromatases, acetylcholinesterases, and monoamine oxidases. 1,2)The monoamine oxidases A and B (EC 1.4.3.4; MAO-A and MAO-B) are flavoenzymes that play an important role in the oxidative degradation of neurotransmitters such as dopamine, serotonin, and epinephrine. MAOs are found in the outer mitochondrial membrane of various mammalian cell types. MAO-A and MAO-B share approximately 70% sequence identity at the amino acid level and were identified based on their substrate selectivities and inhibitor sensitivities. MAO-A preferentially deaminates serotonin, norepinephrine, and epinephrine and is irreversibly inhibited by clorgyline, whereas MAO-B preferentially deaminates dopamine, β-phenetylamine, and benzylamine and is irreversibly inhibited by R-(−)-deprenyl. MAO inhibitors are important in the treatment of several neurodegenerative diseases. Selective MAO-A inhibitors are used as anti-depressant and anti-anxiety drugs whereas selective MAO-B inhibitors are used to treat Parkinson's disease. [3][4][5] Recently, several research groups have reported chromone derivatives substituted at different positions of the chromone ring and their inhibitory e...

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Inhibition of monoamine oxidase by indole and benzofuran derivatives

Cited by 61 publications

References 39 publications

Synthesis of a series of unsaturated ketone derivatives as selective and reversible monoamine oxidase inhibitors

Synthesis of a series of unsaturated ketone derivatives as selective and reversible monoamine oxidase inhibitors

Inhibition of monoamine oxidase by C5-substituted phthalimide analogues

2-Azolylchromone Derivatives as Potent and Selective Inhibitors of Monoamine Oxidases A and B

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