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Chiral Xanthones with Potencial Antioxidant and Anti-inflammatory
Activities: Synthesis and Structure Elucidation
J. Garcia 1 , C. Fernandes 1,2 , M. Pinto 1,2 , M. E. Tiritan 2,3 and C. Afonso 1,2
1 Department of Chemistry, Laboratory of Organic and Pharmaceutical Chemistry, Faculty of
Pharmacy, University of Porto, Rua Aníbal Cunha, 164, 4050-047 Porto, Portugal.
2 CEQUIMED-UP, Center of Medicinal Chemistry – University of Porto, Portugal.
3 CICS-ISCS-N, Gandra, Portugal.
Chiral compounds represent almost one-third of all drug sales worldwide and are of great
importance in Medicinal Chemistry [1]. Some chiral xanthone derivatives (CXD) have
revealed important biological activities with high enantioselectivity [2,3]. There are described
several polyphenolic xanthones with antioxidant and anti-inflammatory effects [4], but no
examples relating CXD with these biological activities.
Considering all these features six new CXD in enantiomerically pure form were synthesized
(Fig. 1) and their structures elucidated by spectroscopic methods ( 1 H NMR, 13 C NMR and IV).
O
O
O
O
CB
CB
N
H 2
O
O
H OH
N
H OH
N
N
H 2
i
OH
N
H 2
O
O
O
O
O
O
OH
CB
CB
i - vi: TBTU, dry tetrahydrofuran, triethylamine, room temperature
ii
OH
vi
N
H 2
iii
v
CB COOH
O
O
N
H 2
iv
H
N
H
N
N
H 2
O
O
3 rd meeting of young researchers at UP 333
OH
OH
O
O
CB
O
CB
H
N
CB: chemical bridge
Fig. 1. Schematic representation of the synthesis of the CXD.
These coupling reactions showed very good yields and short reaction times. All CXD will be
evaluated for their antioxidant and anti-inflammatory activities.
References: [1] Caner, H et al. (2004), Trends in the development of chiral drugs, DDT, 9, (3), 105-
110. [2] Jastrzebska-Wiesek, M. et al. (2003), Central activity of new xanthone derivatives with chiral
center in some pharmacological tests in mice, Pol. J. Pharmacol., 55, 461-465. [3] Sousa, M.E et al.
(2006), Multimilligram enantioresolution of low-solubility xanthonolignoids on polysaccharide chiral
stationary phases using a solid-phase injection system, J. Chromatogr. A, 1120, 75-81. [4] Pinto, M.M.
et al. (2005), Xanthone Derivatives: New Insights in Biological Activities, Curr Med Chem, 12, 2517-
2538.
Acknowledgements: To CEQUIMED-UP (I&D 4040/2007) and to U.Porto/Santander Totta for
financial support.
O
H
N
OH