Synthesis and evaluation of chromone derivatives as inhibitors of monoamine oxidase

Mpitimpiti, Annah N; Petzer, Jacobus P.; Petzer, Anél; Jordaan, Johannes H.; Lourens, Anna C.U.

doi:10.1007/s11030-019-09917-8

Cited by 24 publications

(9 citation statements)

References 55 publications

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“…Initially, the investigation was begun with O -methylhydroxylamine ( i ) (Scheme , Table , entry 9) providing, unexpectedly, a mixture of two types of carbonylated compounds in a ratio of 10:90 ( 2i : 3i ). The GC-MS analysis of the obtained mixture and the detailed NMR comparison of the isolated compounds ( 2i : 3i ), based on the literature, revealed the presence of the corresponding chromone-3-carboxamide ( 2i ) as well as the unexpected 3-functionalized chromane-2,4-dione ( 3i ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Chroman-2,4-diones via Ring-Opening/Ring-Closing Reaction Involving Palladium-Catalyzed Intramolecular Aryloxycarbonylation

Chniti,

Pongrácz,

Kollár

et al. 2024

J. Org. Chem.

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Palladium-catalyzed aminocarbonylation of 3-iodochromone was studied in the presence of primary and secondary amines using atmospheric pressure of carbon monoxide as a carbonyl source. This procedure successfully provided a library of chromone-3-carboxamides and 3-substituted chroman-2,4-diones in 40 to 92% isolated yields. The reaction proceeded via highly chemoselective aminocarbonylation (up to 100%) in the presence of secondary amines by using monodentate or bidentate phosphine ligands. The tendency of 3-iodochromone substrate to undergo ANRORC rearrangement with N-nucleophiles was crucial to shift the reaction toward an unprecedented chemoselective carbonylative transformation, where a late-stage carbonyl insertion is favored concomitantly to the last ring-closure step. The proposed aza-Michael addition/ring-opening/intramolecular aryloxycarbonylation sequence showed compatibility, uniquely, to primary amines when XantPhos was used as a ligand. The solid-state structures of chromone-3-carboxamide (2a) and chroman-2,4-dione (3s) were undoubtedly established by single-crystal XRD analysis. A catalytic cycle was proposed to rationalize the formation of the two types of carbonylated compounds.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Chroman-2,4-diones via Ring-Opening/Ring-Closing Reaction Involving Palladium-Catalyzed Intramolecular Aryloxycarbonylation

Chniti,

Pongrácz,

Kollár

et al. 2024

J. Org. Chem.

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“…Finally, two broad signals around 10-12 ppm were assigned to NH protons of both (Z) and (E) isomers. The signal at a higher chemical shift value was assigned to the (E) isomer because of strong intramolecular H-bonding between H(17) and O (11), while the signal at the lower chemical shift value was assigned to the (Z) isomer due to weak H-bonding between O(12) and H (17) [27,28]. The intensity of the (15) signal around 8.5-8.8 ppm due to (E) and (Z) isomers indicated the presence of the (E) isomer in a higher ratio (72%) than the (Z) isomer (28%), and this was attributed to the extra-stability of (E) isomer due to strong H-bonding.…”

Section: Characterization Of Compounds (4a-4i)mentioning

confidence: 99%

In Silico and In Vitro Studies of 4-Hydroxycoumarin-Based Heterocyclic Enamines as Potential Anti-Tumor Agents

Assad

Paracha²,

Siddique

et al. 2023

Molecules

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The present study reports the one-step synthesis of several 3-formyl-4-hydroxycouramin-derived enamines (4a–4i) in good yields (65–94%). The characterization of the synthesized compounds was carried out via advanced analytical and spectroscopic techniques, such as melting point, electron impact mass spectrometry (EI-MS), 1H-NMR, 13C-NMR, elemental analysis, FTIR, and UV-Visible spectroscopy. The reaction conditions were optimized, and the maximum yield was obtained at 3–4 h of reflux of the reactants, using 2-butanol as a solvent. The potato disc tumor assay was used to assess Agrobacterium tumefaciens-induced tumors to evaluate the anti-tumor activities of compounds (4a–4i), using Vinblastine as a standard drug. The compound 4g showed the lowest IC50 value (1.12 ± 0.2), which is even better than standard Vinblastine (IC50 7.5 ± 0.6). For further insight into their drug actions, an in silico docking of the compounds was also carried out against the CDK-8 protein. The binding energy values of compounds were found to agree with the experimental results. The compounds 4g and 4h showed the best affinities toward protein, with a binding energy value of −6.8 kcal/mol.

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“…Mpitimpiti et al developed a novel series of 15 chromone derivatives and tested their MAO inhibitory activity in light of earlier investigations on the possible inhibition of MAO by chromone compounds [ 54 ]. This study strongly emphasized the third position vs. the potential of MAO inhibition concerning the effect of flexible side chain replacement.…”

Section: Sar Studies Of Chromone As Mao-b Inhibitorsmentioning

confidence: 99%

A Concise Review of the Recent Structural Explorations of Chromones as MAO-B Inhibitors: Update from 2017 to 2023

Ipe,

Kumar,

Benny

et al. 2023

Pharmaceuticals

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Monoamine oxidases (MAOs) are a family of flavin adenine dinucleotide-dependent enzymes that catalyze the oxidative deamination of a wide range of endogenous and exogenous amines. Multiple neurological conditions, including Parkinson’s disease (PD) and Alzheimer’s disease (AD), are closely correlated with altered biogenic amine concentrations in the brain caused by MAO. Toxic byproducts of this oxidative breakdown, including hydrogen peroxide, reactive oxygen species, and ammonia, can cause oxidative damage and mitochondrial dysfunction in brain cells. Certain MAO-B blockers have been recognized as effective treatment options for managing neurological conditions, including AD and PD. There is still a pressing need to find potent therapeutic molecules to fight these disorders. However, the focus of neurodegeneration studies has recently increased, and certain compounds are now in clinical trials. Chromones are promising structures for developing therapeutic compounds, especially in neuronal degeneration. This review focuses on the MAO-B inhibitory potential of several synthesized chromones and their structural activity relationships. Concerning the discovery of a novel class of effective chromone-based selective MAO-B-inhibiting agents, this review offers readers a better understanding of the most recent additions to the literature.

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Synthesis and evaluation of chromone derivatives as inhibitors of monoamine oxidase

Cited by 24 publications

References 55 publications

Synthesis of Chroman-2,4-diones via Ring-Opening/Ring-Closing Reaction Involving Palladium-Catalyzed Intramolecular Aryloxycarbonylation

Synthesis of Chroman-2,4-diones via Ring-Opening/Ring-Closing Reaction Involving Palladium-Catalyzed Intramolecular Aryloxycarbonylation

In Silico and In Vitro Studies of 4-Hydroxycoumarin-Based Heterocyclic Enamines as Potential Anti-Tumor Agents

A Concise Review of the Recent Structural Explorations of Chromones as MAO-B Inhibitors: Update from 2017 to 2023

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