Evaluation of 3-Carboxy-4(1<i>H</i>)-quinolones as Inhibitors of Human Protein Kinase CK2

Golub, Andriy G.; Yakovenko, O. S.; Bdzhola, Volodymyr G.; Sapelkin, Vladislav M.; Zień, Piotr; Yarmoluk, S. M.

doi:10.1021/jm050048t

Cited by 56 publications

(32 citation statements)

References 41 publications

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“…The cyclization of the enamines 16 is realized by the action of heat in high-boiling solvents such as biphenyl [44], biphenyl ether [1, 26,32,34,36,37,41,42,[45][46][47], Dowtherm A [35,38,39,48,49], and mineral oil [1] or by using effective cyclization agents such as polyphosphoric acid or its esters [1, 2], the halogen derivatives of phosphorus [1], ZnCl 2 [1], conc. sulfuric acid in mixture with acetic anhydride [1], and Eaton's reagent (a mixture of phosphorus(V) oxide and methanesulfonic acid) [37,40].…”

Section: Type Dmentioning

confidence: 99%

“…In addition, active researches have been carried out on other types of biological activity in 4-quinolones. The following types of activity have been observed in a series of papers: Antiviral with respect to hepatitis B, C, and HIV viruses [3,4,24] and herpes viruses [3,37], antiallergic [3], antimalarial [68,109], antitubercular [36,39,110], immunomodulating [38], antihypoxic [25], antidiabetic [46]. 4-Quinolones have antithrombocytic [111] and positive cardiotonic activity [24].…”

Section: Biological Activity Of 4-quinolonesmentioning

confidence: 99%

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The methods of synthesis, modification, and biological activity of 4-quinolones (review)

Boteva

Красных

2009

Chem Heterocycl Comp

105

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Data on methods for the construction of the 4-quinolone skeleton and modification of the substituents around it are reviewed. The "structure-activity" relationships of 4-quinolones are examined with respect to antibacterial and antitumor activity.Keywords: 4-quinolones, biological activity. 4-Quinolones have been a subject of research for many scientific teams, and this is reflected in the numerous reviews and monographs devoted to various aspects of the subject. One of the early reviews [1] concerns aspects of the synthesis of individual representatives of the group of 4-quinolones and comparative characterization of their antimicrobial activity. Basic approaches to construction of the fluoroquinolone skeleton and also variation of the substituents at various positions of the ring were examined in the review [2]. The relationship between the structure and antibacterial activity is discussed in [3], and methods for the synthesis of polycyclic derivatives of 4-quinolones based on the annelation of rings to the various faces of the quinoline skeleton are discussed in the review [4]. The reviews [5, 6] were devoted to identification of the structural modifications of 4-quinolones responsible for their conversion from antibacterial agents to antitumor agents. The molecular and biological aspects of the antibacterial action of 4-quinolone-3-carboxylic acids are examined in [7], and issues concerned with the clinical application of 4-quinolones are discussed in the reviews [8][9][10][11][12] and in the monograph [13]. The synthesis and the "structure-activity" relationships of the bioisosteres of 4-quinolones -2-pyridones -are examined in the review [14].The aim of the present review was to classify existing methods for the synthesis not only of fluoroquinolones but also of any 4-quinolones, to demonstrate the effects of modification of the molecule at all positions, to summarize data on the various types of activity, and to examine the "structure-activity" relationship with respect to antibacterial and antitumor activity.

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Section: Type Dmentioning

confidence: 99%

Section: Biological Activity Of 4-quinolonesmentioning

confidence: 99%

The methods of synthesis, modification, and biological activity of 4-quinolones (review)

Boteva

Красных

2009

Chem Heterocycl Comp

105

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“…Even if antimony is a well-known toxic agent, it is used in anti-parasite therapies 172 and this compound can be interesting if related to the role of CK2 in parasite proliferation. The carboxyl acid moiety is also present in the dihydroquinoline derivates 173 selected via receptor-based virtual screening of the Otava compound library. The most active molecule, compound 7 (5,6,8-trichloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, K i 5 0.06 mM), has been tested on a total of 8 PKs and it showed to inhibit CK2 and DYRK1a.…”

Section: Carboxyl Acid Derivativesmentioning

confidence: 99%

How druggable is protein kinase CK2?

2009

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CK2 is a pleiotropic, ubiquitous, and constitutively active protein kinase (PK), with both cytosolic and nuclear localization in most mammalian cells. The holoenzyme is generally composed of two catalytic (alpha and/or alpha') and two regulatory (beta) subunits, but the free alpha/alpha' subunits are catalytically active by themselves and can be present in cells under some circumstances. CK2 catalyzes the phosphorylation of more than 300 substrates characterized by multiple acidic residues surrounding the phosphor-acceptor amino acid, and, consequently, it plays a key role in several physiological and pathological processes. But how can one kinase orchestrate all these tasks faithfully? How is it possible that one kinase can, despite all pleiotropic characteristics of PKs in general, be involved in so many different biochemical events? Is CK2 a druggable target? Several questions are still to be clearly answered, and this review is an occasion for a fruitful discussion.

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“…Earlier, we found protein kinase CK2 inhibitors among the derivatives of 3-carboxy-4(1H)-quinolone 30 . Recently, we have identified hit compound among the derivatives of 3-carboxy quinolin-2-one-7-bromo-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 93 (Figure 1) which decreased activity of CK2 on 22% at concentration of 33 mM 31,32 .…”

Section: Resultsmentioning

confidence: 97%

Design, synthesis and evaluation of 3-quinoline carboxylic acids as new inhibitors of protein kinase CK2

Syniugin

Ostrynska

Chekanov

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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In this article, the derivatives of 3-quinoline carboxylic acid were studied as inhibitors of protein kinase CK2. Forty-three new compounds were synthesized. Among them 22 compounds inhibiting CK2 with IC 50 in the range from 0.65 to 18.2 mM were identified. The most active inhibitors were found among tetrazolo-quinoline-4-carboxylic acid and 2-aminoquinoline-3-carboxylic acid derivatives. KeywordsInhibitor, protein kinase CK2, tetrazolo[1,5-a]quinoline-4-carboxylic acid, 2-aminoquinoline-3-carboxylic acid, 2-chloroquinoline-3-carboxylic acid, 2-oxo-1,2-dihydroquinoline-3-carboxylic acid, 5-oxo-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxylic acid History

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Evaluation of 3-Carboxy-4(1H)-quinolones as Inhibitors of Human Protein Kinase CK2

Cited by 56 publications

References 41 publications

The methods of synthesis, modification, and biological activity of 4-quinolones (review)

The methods of synthesis, modification, and biological activity of 4-quinolones (review)

How druggable is protein kinase CK2?

Design, synthesis and evaluation of 3-quinoline carboxylic acids as new inhibitors of protein kinase CK2

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