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Dual application of chiral derivatives of xanthones in medicinal chemistry and liquid chromatography
* 1, 2 , 2, 3 , 1 , 1, 2 , 1, 2, 4 , 5 , 2, 3 , 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  ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
4  CESPU, Instituto de Investigação e Formação Avançada em Ciências e Tecnologias da Saúde, Rua Central de Gandra, 1317, 4585-116 Gandra PRD, Portugal
5  Departamento de Química, Universidade de Aveiro, 3810-193 Aveiro, Portugal

Published: 31 October 2018 by MDPI in 4th International Electronic Conference on Medicinal Chemistry session ECMC-4

Over several years, xanthone derivatives have been the core of several studies, essentially due their wide range of biological and pharmacological activities [1]. Recently, chiral derivatives of xanthones (CDXs) have come to arouse great interest considering enantioselectivity studies associated with biological activities [2,3] as well as selectors for chiral stationary phases (CSPs) in liquid chromatography (LC) [4,5].

From the perspective of Medicinal Chemistry, some CDXs synthetized by our group revealed interesting biological activities [2,3]. Besides the potential as new drugs, CDXs afford promising LC enantioresolution results [6].

In a continuation of our study, new enantiomerically pure CDXs were synthetized for biological activity evaluation as well as selectors for new CSPs, confirming that CDXs have important applications not only in the field of Medicinal Chemistry but also for analytical applications.


This research was partially supported by the Strategic Funding UID/Multi/04423/2013 and UID/QUI/00062/2013 through national funds provided by FCT and ERDF, in the framework of PT2020, by projects PTDC/MAR-BIO/4694/2014 (reference POCI-01-0145-FEDER-016790; Project 3599-PPCDT), and project No. POCI-01-0145-FEDER-028736, co-financed by COMPETE 2020, Portugal 2020 and the European Union through the ERDF, and by FCT through national funds, as well as by the Portuguese NMR Network, and CHIRALXANT-CESPU-2018.

[1] Shagufta, A.I. Eur. J. Med. Chem., 2016, 116, 267-280.

[2] Fernandes, C. et al. Bioorg. Med. Chem. 2014, 22, 1049-1062.

[3] Fernandes, C. et al. Pharmaceuticals, 2017, 10, 50, doi:10.3390/ph10020050.

[4] Phyo, Y.Z. et al. Molecules, 2018, 23, 142, doi:10.3390/molecules23010142.

[5] Carraro, M.L. et al. Chirality, 2017, 1–10

[6] Fernandes, C. et al. Chirality, 2017, 29(8),430-442.

Keywords: chiral derivatives of xanthones; biological activity; chiral stationary phases; liquid chromatography; enantioselectivity