Planta Medica International Open 2017; 4(S 01): S1-S202
DOI: 10.1055/s-0037-1608257
Poster Session
Georg Thieme Verlag KG Stuttgart · New York

Synthesis of new, potentially bioactive chalcones as protoflavone analogues

T Gonda
1   Institute of Pharmacognosy, University of Szeged, Szeged, Hungary
,
B Ötvös Sándor
2   Institute of Pharmaceutical Chemistry, University of Szeged, Szeged, Hungary
3   MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, Szeged, Hungary
,
A Hunyadi
1   Institute of Pharmacognosy, University of Szeged, Szeged, Hungary
4   Interdisciplinary Centre for Natural Products, University of Szeged, Szeged, Hungary
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Publikationsverlauf

Publikationsdatum:
24. Oktober 2017 (online)

 
 

    Protoflavones represent a rare, unique class of naturally occurring bioactive flavonoid derivatives. Recent publications revealed their antiviral, anti-angiogenic and cytotoxic activity, moreover they have also been found to interfere with crucial DNA damage response mechanisms[1 – 3]. The pharmacophore of these compounds is the non-aromatic B-ring – the unusual p-quinol moiety[3]. The formation of this moiety can be synthetically achieved from 4 ′ -hydroxyflavones applying hypervalent iodine reagents.

    Chalcones – also abundant in nature – exert anti-inflammatory, antioxidant, antibacterial and anticancer activity; anti-angiogenic effect of 4-hydroxychalcone 3 was reported lately[4].

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    During the current project our aim is – in order to broaden our knowledge on structure-activity relationships concerning protoflavones – to build a compound library by synthesizing and characterizing variously substituted chalcone analogues bearing the p-quinol moiety.

    The key intermedier 4-hydroxychalcone 3 was synthesysed via Claisen-Schmidt condensation. Seven new compounds (4-10) were subsequently obtained by oxidative dearomatization performed with PIFA in various solvent mixtures. These compounds are expected to exert potent antitumor activity; their bioactivity testing is currently in progress.

    This work was supported by the NKFIH, Hungary (K119770), the EU-funded Hungarian grant EFOP-3.6.1 – 16 – 2016 – 00008, and GINOP-2.3.2 – 15 – 2016 – 00012. A.H. acknowledges the János Bolyai fellowship of the Hungarian Academy of Sciences and the Kálmán Szász Prize.

    [1] Danko B et al. Anticancer Res 2012; 32: 2863 – 2870.

    [2] Wang HC et al. Mol. Cancer Ther 2012; 11:1443 – 1453.

    [3] Hunyadi A et al. Phytochem Rev 2014; 13: 69 – 77.

    [4] Varinska L et al. Eur J Pharmacol 2012; 691: 125 – 133.


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