Flavone inspired discovery of benzylidenebenzofuran-3(2H)-ones (aurones) as potent inhibitors of human protein kinase CK2

Protopopov, M. V.; Vdovin, Vasyl; Starosyla, Sergiy A.; Borysenko, I. P.; Prykhod'ko, A.O.; Lukashov, S. S.; Bilokin, Yaroslav V.; Bdzhola, Volodymyr G.; Yarmoluk, S. M.

doi:10.1016/j.bioorg.2020.104062

Cited by 14 publications

(4 citation statements)

References 49 publications

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“…Compound 44 was one of the most active aurones of the series (IC 50 = 3.3 nM). 64 Altogether, these studies constitute promising starting points for further modulation endeavors. Besides kinases, histone deacetylases (HDACs) are also widely associated with cancer development.…”

Section: Inhibition Of Poly(adp-ribose)polymerases (Parps)mentioning

confidence: 99%

“…A further exploration of anti-CK2 properties of aurones afforded numerous compounds with nanomolar activities, with a clear beneficial effect of substituents at position 3′. Compound 44 was one of the most active aurones of the series (IC 50 = 3.3 nM) . Altogether, these studies constitute promising starting points for further modulation endeavors.…”

Section: Biological Activities Of Hemiindigoidsmentioning

confidence: 99%

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Bioactive Aurones, Indanones, and Other Hemiindigoid Scaffolds: Medicinal Chemistry and Photopharmacology Perspectives

et al. 2022

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Hemiindigoids comprise a range of natural and synthetic scaffolds that share the same aromatic hydrocarbon backbone as well as promising biological and optical properties. The encouraging therapeutic potential of these scaffolds has been unraveled by many studies over the past years and uncovered representants with inspiring pharmacophoric features such as the acetylcholinesterase inhibitor donezepil and the tubulin polymerization inhibitor indanocine. In this review, we summarize the last advances in the medicinal potential of hemiindigoids, with a special attention to molecular design, structure–activity relationship, ligand-target interactions, and mechanistic explanations covering their effects. As their strong fluorogenic potential and photoswitch behavior recently started to be highlighted and explored in biology, giving rise to the development of novel fluorescent probes and photopharmacological agents, we also discuss these properties in a medicinal chemistry perspective.

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Section: Inhibition Of Poly(adp-ribose)polymerases (Parps)mentioning

confidence: 99%

Section: Biological Activities Of Hemiindigoidsmentioning

confidence: 99%

Bioactive Aurones, Indanones, and Other Hemiindigoid Scaffolds: Medicinal Chemistry and Photopharmacology Perspectives

et al. 2022

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“…For example, nitro flavone derivative exhibits the cytotoxic activity [29], 4′-nitro-6hydroxyflavone suppresses the activity of HNF4α and stimulates the degradation of HNF4α protein [30], 4-nitro aurone is potential inhibitor of H1N1 virus [31], 5-nitro derivative of protocatechuic aldehyde can be potential agent for the treatment of gout and hyperuricemia [32]. Recently, some of the nitro-substituted aurones have been described as inhibitors of human protein kinase CK2 [33,34]. In the present study we evaluated the aurone derivatives having a nitro group in the B-ring as XO inhibitors.…”

Section: Introductionmentioning

confidence: 99%

Nitro-substituted aurones as xanthine oxidase inhibitors

et al. 2021

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Aurone derivatives possessing a wide range of biological activities are of high interest in medicinal chemistry. Carboxylated aurones were found previously to inhibit xanthine oxidase, which is a potential target for treatment of hyperuricemia and gout. In this paper, a series of B-ring nitro-substituted aurone derivatives were studied in vitro as inhibitors of this enzyme. The introduction of hydroxyl group into the B-ring of nitro-functionalized aurones resulted in significant increase of their inhibitory potency. At the same time, aurones chlorinated at ring A and containing nitro and hydroxyl groups at ring B showed only slightly increased inhibition effect. The kinetic studies and molecular docking calculations were carried out to explain the inhibition mechanism of xanthine oxidase by the nitro-substituted aurone derivatives

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“…The search for CK2 inhibitors has been carried out for over 20 years [9,10]. Most of the identified CK2 inhibitors belong to coumarins [11], halogenated benzimidazoles (ТВВ) [12], anthraquinones (emodin) [13], indoloquinazolines (IQA) [14], thieno [2,3-d] pyrimidines [15,16], 4,5,6,7-tetrahalogeno-1H-isoindole-1,3(2H)-diones [17], flavones derivatives (luteolin, FLC26, FNH79) [18][19][20], 1,3-thiazole-5-carboxylic acid derivatives [21], quinolones [22], aurones [23,24] and naphthyridines (CX-4945, CX-5011) [25,26].…”

Section: Introductionmentioning

confidence: 99%

The synthesis of 5-hetarylamino-3-aryl-1H-indazoles as inhibitors of protein kinase CK2

et al. 2020

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Flavone inspired discovery of benzylidenebenzofuran-3(2H)-ones (aurones) as potent inhibitors of human protein kinase CK2

Cited by 14 publications

References 49 publications

Bioactive Aurones, Indanones, and Other Hemiindigoid Scaffolds: Medicinal Chemistry and Photopharmacology Perspectives

Bioactive Aurones, Indanones, and Other Hemiindigoid Scaffolds: Medicinal Chemistry and Photopharmacology Perspectives

Nitro-substituted aurones as xanthine oxidase inhibitors

The synthesis of 5-hetarylamino-3-aryl-1H-indazoles as inhibitors of protein kinase CK2

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