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.
Export Options
About this article
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
Advances of Heterocyclic Chemistry with Pesticide Activity
Global food safety and security will continue to be a global concern for the next 50 years and beyond. Plant diseases have had a significant impact on food safety and security throughout the entire food chain, from primary production to consumption. While conventional chemical pesticides have been traditionally used for ...read more
Calculation design of covalent/metal organic framework based catalysts
This research area combines theoretical computation and screening with machine learning for the design of covalent/metal organic framework-based catalysts, bridging the disciplines of organic chemistry, physical chemistry, computational chemistry, materials science, and machine learning. It covers several critical aspects: designing and synthesizing organic catalysts for improved performance, applying computational methods ...read more
Carbohydrates conversion in biofuels and bioproducts
Biomass pretreatment, hydrolysis, and saccharification of carbohydrates, and sugars bioconversion in biofuels and bioproducts within a biorefinery framework. Carbohydrates derived from woody biomass, agricultural wastes, algae, sewage sludge, or any other lignocellulosic feedstock are included in this issue. Simulation, techno-economic analysis, and life cycle analysis of a biorefinery process are ...read more
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
Related Journals
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
- Announcements
Related Articles
-
Anti-Cancer/Anti-Tumor
Current Bioactive Compounds PEDF as an Emerging Therapeutic Candidate for Osteosarcoma
Current Cancer Drug Targets Angiogenesis: A Target for Cancer Therapy
Current Pharmaceutical Design Nanomedicine Strategies for Sustained, Controlled and Targeted Treatment of Alzheimer’s Disease
Mini-Reviews in Medicinal Chemistry Role of Infrared Spectroscopy and Imaging in Cancer Diagnosis
Current Medicinal Chemistry Implications of Fibroblast Growth Factors (FGFs) in Cancer: From Prognostic to Therapeutic Applications
Current Drug Targets Inorganic Nanoparticles for Enhanced Photodynamic Cancer Therapy
Current Drug Discovery Technologies Hepatocyte Growth Factor Signaling in Cancer Metastasis
Current Signal Transduction Therapy 2,4-Thiazolidinedione as Precursor to the Synthesis of Compounds with Anti-glioma Activities in C6 and GL261 Cells
Medicinal Chemistry Functionalized magnetic nanoparticles for biomedical applications
Current Pharmaceutical Design Curcumin in Combined Cancer Therapy
Current Pharmaceutical Design LAT1 Targeted Delivery of Methionine Based Imaging Probe Derived from M(III) Metal Ions for Early Diagnosis of Proliferating Tumours using Molecular Imaging Modalities
Current Cancer Drug Targets Network Pharmacology of Glioblastoma
Current Drug Discovery Technologies Editorial [Hot Topic: Mechanisms of Drug Sensitivity and Resistance in Cancer (Guest Editor: Lorraine ODriscoll)]
Current Cancer Drug Targets Equinatoxin II Potentiates Temozolomide- and Etoposide-Induced Glioblastoma Cell Death
Current Topics in Medicinal Chemistry Mechanisms and Inhibitors of Apoptosis in Cardiovascular Diseases
Current Pharmaceutical Design Chemistry of Tumour Targeted T1 Based MRI Contrast Agents
Current Topics in Medicinal Chemistry Thymoquinone: Major Molecular Targets, Prominent Pharmacological Actions and Drug Delivery Concerns
Current Bioactive Compounds VEGF, Angiopoietin-1 and -2 in Bronchial Asthma: New Molecular Targets in Airway Angiogenesis and Microvascular Remodeling
Recent Patents on Inflammation & Allergy Drug Discovery Isoform-Selective PI3K Inhibitors for Various Diseases
Current Topics in Medicinal Chemistry