16:00 - 18:00
Room: San Francisco
Poster session
Synthesis of new, potentially bioactive chalcones as protoflavone analogues
Gonda Tímea 1, Ötvös Sándor Balázs 2, 3, Hunyadi Attila 1, 4
1 Institute of Pharmacognosy, University of Szeged, Szeged, Hungary
2 Institute of Pharmaceutical Chemistry, University of Szeged, Szeged, Hungary
3 MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, Szeged, Hungary
4 Interdisciplinary Centre for Natural Products, University of Szeged, Szeged, Hungary

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 ʹ -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].

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.

Acknowledgements:

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.

References:

[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.


Reference:
Mo-Poster Session 1-PO-210:
Session:
Poster Session 1
Presenter/s:
Attila Hunyadi
Presentation type:
Poster presentation
Room:
San Francisco
Date:
Monday, 4th September, 2017
Time:
16:00 - 18:00
Session times:
16:00 - 18:00