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Review
. 2019 Nov 14;24(22):4115.
doi: 10.3390/molecules24224115.

5,8-Quinolinedione Scaffold as a Promising Moiety of Bioactive Agents

Monika Kadela-Tomanek  1 , Ewa Bębenek  1 , Elwira Chrobak  1 , Stanisław Boryczka  1
Affiliations
Review

5,8-Quinolinedione Scaffold as a Promising Moiety of Bioactive Agents

Monika Kadela-Tomanek et al. Molecules. .

Abstract

Natural 5,8-quinolinedione antibiotics exhibit a broad spectrum of activities including anticancer, antibacterial, antifungal, and antimalarial activities. The structure-activity research showed that the 5,8-quinolinedione scaffold is responsible for its biological effect. The subject of this review report is a presentation of the pharmacological activity of synthetic 5,8-quinolinedione compounds containing different groups at C-6 and/or C-7 positions. The relationship between the activity and the mechanism of action is included if these data have been included in the original literature. The review mostly covers the period between 2000 and 2019. Previously published literature data were used to present historical points.

Keywords: 5,8-quinolinedione; NAD[P]H-quinone oxidoreductase; biological activity; streptonigrin.

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Conflict of interest statement

The authors declare no conflicts of interest.

Figures

Figure 1
Figure 1
Structure of natural 5,8-quinolinedione antibiotics 1–5.
Scheme 1
Scheme 1
Synthesis of compounds 7–9.
Scheme 2
Scheme 2
Synthesis of amine derivatives of 5,8-quinolinedione.
Scheme 3
Scheme 3
Synthesis of alkoxy derivatives of 5,8-quinolinedione.
Scheme 4
Scheme 4
Synthesis of thiol derivatives of 5,8-quinolinedione.
Figure 2
Figure 2
Structure of [4-(4-methylpiperazin-1-yl)phenyl]aminoquinoline-5,8-diones 10–11.
Figure 3
Figure 3
Structure of arylamino-5,8-quinolinediones 12–23.
Figure 4
Figure 4
Structure of 6-arylamine 24–26 and multicyclic compounds of 5,8-quinoliniedione 27–34.
Figure 5
Figure 5
Structure of imidazo-5,8-quinolindiones 35–36 and thiazolo-5,8-quinolinediones 37–38.
Figure 6
Figure 6
Structure of alkylamino-5,8-quinolinediones 39–42.
Figure 7
Figure 7
Structure of alkynylamino-5,8-quinolinediones 43–46.
Figure 8
Figure 8
Structure of alkylamino-5,8-quinolinediones 47–50 and their modifications 51–54.
Figure 9
Figure 9
Structure of 2-methylaziridinyl-5,8-quinolinediones 55–60.
Figure 10
Figure 10
Structure of alkoxy-5,8-quinolinediones 61–74.
Figure 11
Figure 11
Structure of enediyne derivatives of 5,8-quinolinedione 73–74.
Figure 12
Figure 12
Structure of hybrids betulin-5,8-quinolinedione 75–77.
Figure 13
Figure 13
Structure of benzofuro-5,8-quinolinediones 78–79.
Figure 14
Figure 14
Structure of arylamine (80–82) and thiol (83–85 and 86–89) derivatives of 5,8-qinolinedione.
Figure 15
Figure 15
Structure of dihydropyrrole derivatives of 5,8-quinolinedione 90–93.
Figure 16
Figure 16
Structure of hybrids alkyne-5,8-quinolinedione 94–99.
Figure 17
Figure 17
Structure of aliphatic amine derivatives of 5,8-quinolinedione 100–105.
Figure 18
Figure 18
Structure of alkylamino-5,8-quinolinediones 106–113.
Figure 19
Figure 19
Structure of methyl derivatives of 5,8-quinolinedione 114–117.
Figure 20
Figure 20
Structure of biphenyl-4-amino-5,8-quinolinediones 118–123.
Figure 21
Figure 21
Structure of disubstituted derivatives of 5,8-quinolinedione 124–127.
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References

    1. Nepal K.K., Wang G. Streptomycetes: Surrogate hosts for the genetic manipulation of biosynthetic gene clusters and production of natural products. Biotechnol. Adv. 2019;37:1–20. doi: 10.1016/j.biotechadv.2018.10.003. - DOI - PMC - PubMed
    1. Rao K.V., Cullen W.P. Streptonigrin, an antitumor substance. I. Isolation and characterization. Antibiot. Annu. 1959;7:950–953. - PubMed
    1. Kudrina E.S., Ol’khovatova O.L., Murav’eva L.I., Gauze G.F. Systematic position and variability of the producent of antitumor antibiotic bruneomycin. Antibiotiki (Mocsow) 1966;11:400–405. - PubMed
    1. Societe des Usines Chemiques Rhone-Poulenc. 8,722,61. British Patent. 1961 Jul 5;
    1. Rao K.V., Biemann K., Woodward R.B. The structure of Streptonigrin. J. Am. Chem. Soc. 1963;85:2532–2533. doi: 10.1021/ja00899a051. - DOI

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