A new series of flavones, thioflavones, and flavanones as selective monoamine oxidase-B inhibitors

Chimenti, Franco; Fioravanti, Rossella; Bolasco, Adriana; Chimenti, Paola; Secci, Daniela; Rossi, Francesca; Yáñez, Matilde; Orallo, Francisco; Ortuso, Francesco; Alcaro, Stefano; Cirilli, Roberto; Ferretti, Rosella; Sanna, Maria Luisa

doi:10.1016/j.bmc.2009.12.029

Cited by 89 publications

(48 citation statements)

References 39 publications

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“…In fact, chalcones have been used in the synthesis of pyrazoline derivatives as part of an effort to discover novel MAO inhibitors. [23][24][25][26][27][28][29][30] Literature reports that, with the appropriate substitution, chalcones themselves are, however, high potency MAO-B inhibitors. For example, synthetic chalcone 2 inhibits human MAO-B with an IC 50 value of 0.0044 lM.…”

mentioning

confidence: 99%

Monoamine oxidase inhibitory activities of heterocyclic chalcones

Minders

Petzer

et al. 2015

Bioorganic & Medicinal Chemistry Letters

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confidence: 99%

Monoamine oxidase inhibitory activities of heterocyclic chalcones

Minders

Petzer

et al. 2015

Bioorganic & Medicinal Chemistry Letters

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“…Flavonoids are important polyphenolic constituents of vegetables, fruits, tea and wine, 9,10) and are well known to exhibit various favorable pharmacological activities, including anti-inflammation, anti-osteoporosis, anticancer, antivirus, anti-bacteria and anti-oxidation. [11][12][13][14][15][16] In general, the structures of flavonoids consist of three aromatic rings designated as ring A, B and C based on the sequence of their biogenesis.…”

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confidence: 99%

Synthesis and Anti-influenza Activities of Novel Baicalein Analogs

Chung

Chien

Yao

et al. 2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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A series of novel flavones derivatives were synthesized based on modification of the active ingredients of a traditional Chinese medicine Scutellaria baicalensis GEORGI and screened for anti-influenza activity. The synthetic baicalein (flavone) analogs, especially with the B-rings substituted with bromine atoms, were much more potent than oseltamivir or ribavirin against H1N1 Tamiflu-resistant (H1N1 TR) virus and usually with more favorable selectivity. The most promising were 5b, 5c, 6b and 6c, all displaying an 50% effective concentration (EC 50 ) at around 4.0-4.5 µM, and a selective index (SI 50% cytotoxic concentration (CC 50 )/ EC 50 )>70. For seasonal H3N2-infected influenza virus, both 5a and 5b with SI >17.3 indicated superior to ribavirin. The flavonoids having both not-naturally-occurring bromo-substituted B-rings and appropriate hydroxyls positioning on the A-rings might be critical in determining the activity and selectivity against H1N1-Tamiflu-resistant infected influenza viruses.

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“…As an exploration of the application of this protocol, the synthetic transformation is shown in Scheme 2. 7-Methoxyflavanone 6, a flavonoid natural product with a variety of biological activities, [15] could Table 2. Substrate scope of N-acetyl hydrazones.…”

Section: Full Paper Ascwiley-vchdementioning

confidence: 99%

Synthesis of Isoquinoline Derivatives via Palladium‐Catalyzed C−H/C−N Bond Activation of N‐Acyl Hydrazones with α‐Substituted Vinyl Azides

Nie

Zeng

et al. 2020

Adv Synth Catal

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A palladium‐catalyzed cyclization of N‐acetyl hydrazones with vinyl azides has been developed. Various substituted isoquinolines, including diverse fused isoquinolines can be prepared via this protocol in moderate to good yields. Mechanistic studies suggest that α‐substituted vinyl azide serves as an internal nitrogen source. Also, C−H bond activation and C−N bond cleavage have been realized using hydrazone as directing group.

show abstract

A new series of flavones, thioflavones, and flavanones as selective monoamine oxidase-B inhibitors

Cited by 89 publications

References 39 publications

Monoamine oxidase inhibitory activities of heterocyclic chalcones

Monoamine oxidase inhibitory activities of heterocyclic chalcones

Synthesis and Anti-influenza Activities of Novel Baicalein Analogs

Synthesis of Isoquinoline Derivatives via Palladium‐Catalyzed C−H/C−N Bond Activation of N‐Acyl Hydrazones with α‐Substituted Vinyl Azides

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