Abstract
Xanthones or 9H-xanthen-9-ones (dibenzo-γ-pyrones) comprise an important class of oxygenated heterocycles, with prenylated derivatives being the most abundant group. The prenylated xanthones are found to possess a wide range of important biological and pharmacological activities. As a consequence of this, synthetic strategies leading to new and more complex molecules have been widely explored in the past years. In our literature survey, from January 1963 to March 2009, a total of 93 synthetic prenylated xanthones were described and 24 of them were firstly obtained from natural sources. Thus, the main purpose of this review is to report synthetic methods to obtain prenylated xanthones, such as simple prenylation, Claisen rearrangement and/or cyclization. We also discuss the application of new methodologies to the synthesis of prenylated derivatives, such as microwave assisted organic synthesis, heterogeneous catalysis with Montmorillonite K10 Clay as catalyst and the combination of heterogeneous catalysis with microwave irradiation. Furthermore, different approaches and methodologies used to synthesize bioactive natural prenylated xanthones, like α-mangostin, are also discussed. Finally, biological activities of prenylated xanthones are also briefly referred.
Current Organic Chemistry
Title: Synthesis of Prenylated Xanthones: An Overview
Volume: 13 Issue: 12
Author(s): M. M. M. Pinto and R. A. P. Castanheiro
Affiliation:
Abstract: Xanthones or 9H-xanthen-9-ones (dibenzo-γ-pyrones) comprise an important class of oxygenated heterocycles, with prenylated derivatives being the most abundant group. The prenylated xanthones are found to possess a wide range of important biological and pharmacological activities. As a consequence of this, synthetic strategies leading to new and more complex molecules have been widely explored in the past years. In our literature survey, from January 1963 to March 2009, a total of 93 synthetic prenylated xanthones were described and 24 of them were firstly obtained from natural sources. Thus, the main purpose of this review is to report synthetic methods to obtain prenylated xanthones, such as simple prenylation, Claisen rearrangement and/or cyclization. We also discuss the application of new methodologies to the synthesis of prenylated derivatives, such as microwave assisted organic synthesis, heterogeneous catalysis with Montmorillonite K10 Clay as catalyst and the combination of heterogeneous catalysis with microwave irradiation. Furthermore, different approaches and methodologies used to synthesize bioactive natural prenylated xanthones, like α-mangostin, are also discussed. Finally, biological activities of prenylated xanthones are also briefly referred.
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Cite this article as:
Pinto M. M. M. and Castanheiro A. P. R., Synthesis of Prenylated Xanthones: An Overview, Current Organic Chemistry 2009; 13 (12) . https://dx.doi.org/10.2174/138527209788921747
DOI https://dx.doi.org/10.2174/138527209788921747 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Chemistry and Biology of Carbohydrates
Carbohydrates are one of the most abundant natural products and are considered to be extremely important biomolecules for their ever-increasing impact on chemistry and biology. Their role in several important biological processes, notably energy storage, transport, modulation of protein function, intercellular adhesion, malignant transformation, signal transduction, viral, and bacterial cell ...read more
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