Abstract
Many naturally occurring xanthones are chiral and present a wide range of biological and pharmacological activities. Some of them have been exhaustively studied and subsequently, obtained by synthesis. In order to obtain libraries of compounds for structure activity relationship (SAR) studies as well as to improve the biological activity, new bioactive analogues and derivatives inspired in natural prototypes were synthetized. Bioactive natural xanthones compromise a large structural multiplicity of compounds, including a diversity of chiral derivatives. Thus, recently an exponential interest in synthetic chiral derivatives of xanthones (CDXs) has been witnessed. The synthetic methodologies can afford structures that otherwise could not be reached within the natural products for biological activity and SAR studies. Another reason that justifies this trend is that both enantiomers can be obtained by using appropriate synthetic pathways, allowing the possibility to perform enantioselectivity studies. In this work, a literature review of synthetic CDXs is presented. The structures, the approaches used for their synthesis and the biological activities are described, emphasizing the enantioselectivity studies.
Highlights
In the last few years, the relationship between chirality and biological activity has been of increasing importance in Medicinal Chemistry [1]
These experiments were preliminary, the results suggested that promising agents with anti-tumor activities could be obtained by modification at C-2 position of the B ring and
The structure activity relationship (SAR) studies suggested that compounds 151, 153, and 154 showed similar cytotoxicity to gambogic acid against A549 cells, whereas compounds 149–151 and 152 were less active than gambogic acid. These experiments were preliminary, the results suggested that promising agents with anti-tumor activities could be obtained by modification at C-2 position of the B ring and at C-21/22 or C-23 position of the prenyl group in the caged scaffold
Summary
In the last few years, the relationship between chirality and biological activity has been of increasing importance in Medicinal Chemistry [1]. Xanthones (9H-xanthen-9-ones) are compounds with an oxygen-containing dibenzo-γ-pyrone heterocyclic scaffold [27], being considered as a privileged structure [28,29] Within this class of compounds a broad range of biological and pharmacological activities has been reported [30,31,32,33,34]. The biosynthetic pathway of xanthones only allows the presence of specific groups in particular positions of the xanthone scaffold, which is a limiting factor for structural diversity For this reason, in order to enlarge chemical space in this field, total synthesis needs to be considered [41,42] allowing the access to structures that otherwise could not be reached only with natural product as a basis for molecular modification. Higher number of compounds can be obtained for SAR studies
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