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Synthesis and enantiomeric purity evaluation of a new small library of promising bioactive chiral derivatives of xanthones
* 1, 2 , 1 , 1 , 1 , 1, 2, 3 , 4 , 1, 2
1  Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, Rua Jorge Viterbo Ferreira nº 228, 4050-313 Porto, Portugal
2  Centro Interdisciplinar de Investigação Marinha e Ambiental (CIIMAR), Universidade do Porto, Edifício do Terminal de Cruzeiros do Porto de Leixões, Av. General Norton de Matos s/n, 4050-208 Matosinhos, Portugal
3  CESPU, Instituto de Investigação e Formação Avançada em Ciências e Tecnologias da Saúde, Rua Central de Gandra, 1317, 4585-116 Gandra PRD, Portugal
4  Departamento de Química, Universidade de Aveiro, 3810-193 Aveiro, Portugal

Published: 02 November 2015 by MDPI in 1st International Electronic Conference on Medicinal Chemistry session ECMC-1

For the last years, searching new chiral derivatives of xanthones (CDX) with potential pharmacological properties has remained in the area of interest of our group [1,2]. Recently, we have described the ability of CDX to inhibit the growth of different human tumor cell lines [1]. In fact, some of them exhibited interesting dose-dependent growth inhibitory effects on the evaluated cell lines being dependent on the stereochemistry.

Based on this work, herein we describe the synthesis of a new library of promising bioactive analogues, in enantiomerically pure form, with good yields, short reaction times and no racemization. The optimization of the synthetic pathways to obtain the xanthonic derivative used as chemical building block was also described.

The enantiomeric excesses for all synthesized CDX were measured by HPLC on (S,S)-Whelk-O1® chiral stationary phase under polar-organic elution conditions, achieving values higher than 99%.

The evaluation of growth inhibitory activity on human tumor cell lines of the synthesized CDX is in progress.



This research was partially supported by the Strategic Funding UID/Multi/04423/2013 and UID/QUI/00062/2013 through national funds provided by FCT – Foundation for Science and Technology and European Regional Development Fund (ERDF), in the framework of the programme PT2020, and the Portuguese NMR Network.



[1] Fernandes C.; Masawang K.; Tiritan M. E.; Sousa E.; Lima V.; Afonso C.; Bousbaa H.; Sudprasert W.; Pedro M.; Pinto M. M. Bioorgan. Med. Chem. 2014, 22, 1049.

[2] Fernandes, C.; Oliveira, L.; Tiritan, M. E.; Leitao, L.; Pozzi, A.; Noronha-Matos, J. B.; Correia-de-Sá, P.; Pinto, M. M., Eur. J. Med. Chem., 2012, 55, 1.

Keywords: Chiral derivatives of xanthones; Synthesis; Enantiomeric purity.
Comments on this paper
Maria Emília Sousa
Chiral drugs
Quite multidisciplinar work, congratulations!

Mariia Nesterkina
Good job
Very useful and detailed presentation. Thanks a lot for your job.