Recent advances in the synthesis of xanthones and azaxanthones

Resende, Diana I. S. P.; Durães, Fernando; Maia, Mariana; Sousa, Emı́lia; Pinto, Madalena

doi:10.1039/d0qo00659a

Cited by 54 publications

(29 citation statements)

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“…A library of 20 xanthones with diverse substituents was investigated based on preliminary antibacterial activity and synergy studies [ 13 , 15 , 25 ] against a RND efflux pump model present in Gram-negative bacteria (AcrAB-TolC) and a homology model of the major facilitator superfamily (MFS) efflux pump NorA, prevalent in Gram-positive bacteria. In this study, the used library of xanthones was obtained in-house.…”

Section: Resultsmentioning

confidence: 99%

Xanthones Active against Multidrug Resistance and Virulence Mechanisms of Bacteria

et al. 2021

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The emergence of multidrug and extensively drug-resistant pathogenic bacteria able to resist to the action of a wide range of antibiotics is becoming a growing problem for public health. The search for new compounds with the potential to help in the reversion of bacterial resistance plays an important role in current medicinal chemistry research. Under this scope, bacterial efflux pumps are responsible for the efflux of antimicrobials, and their inhibition could reverse resistance. In this study, the multidrug resistance reversing activity of a series of xanthones was investigated. Firstly, docking studies were performed in the AcrAB-TolC efflux pump and in a homology model of the NorA pump. Then, the effects of twenty xanthone derivatives on bacterial growth were evaluated in Staphylococcus aureus 272123 and in the acrA gene-inactivated mutant Salmonella enterica serovar Typhimurium SL1344 (SE03). Their efflux pump inhibitory properties were assessed using real-time fluorimetry. Assays concerning the activity of these compounds towards the inhibition of biofilm formation and quorum sensing have also been performed. Results showed that a halogenated phenylmethanamine xanthone derivative displayed an interesting profile, as far as efflux pump inhibition and biofilm formation were concerned. To the best of our knowledge, this is the first report of xanthones as potential efflux pump inhibitors.

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Section: Resultsmentioning

confidence: 99%

Xanthones Active against Multidrug Resistance and Virulence Mechanisms of Bacteria

et al. 2021

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“…This collection of xanthones allowed to establish structure-NMR chemical shift relationships [ 43 ] and gather X-ray crystallographic data [ 44 , 45 ] to guide synthetic chemists. Also, this appendance diversity-oriented synthesis allowed to develop a chemical toolbox of synthetic conditions and intermediates, based on classical and novel methods to obtain xanthones, recently reviewed in [ 46 ] and to establish methods for their quantification validated in a diversity of matrices [ 47 ].…”

Section: A Library Of Natural Mimetic Xanthones Looking For Biologmentioning

confidence: 99%

From Natural Products to New Synthetic Small Molecules: A Journey through the World of Xanthones

et al. 2021

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This work reviews the contributions of the corresponding author (M.M.M.P.) and her research group to Medicinal Chemistry concerning the isolation from plant and marine sources of xanthone derivatives as well as their synthesis, biological/pharmacological activities, formulation and analytical applications. Although her group activity has been spread over several chemical families with relevance in Medicinal Chemistry, the main focus of the investigation and research has been in the xanthone family. Xanthone derivatives have a variety of activities with great potential for therapeutic applications due to their versatile framework. The group has contributed with several libraries of xanthones derivatives, with a variety of activities such as antitumor, anticoagulant, antiplatelet, anti-inflammatory, antimalarial, antimicrobial, hepatoprotective, antioxidant, and multidrug resistance reversal effects. Besides therapeutic applications, our group has also developed xanthone derivatives with analytical applications as chiral selectors for liquid chromatography and for maritime application as antifouling agents for marine paints. Chemically, it has been challenging to afford green chemistry methods and achieve enantiomeric purity of chiral derivatives. In this review, the structures of the most significant compounds will be presented.

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“…Over the years, notable progress has been made in xanthone synthesis by utilizing different substrates and methods [10] . However, there is a scarcity of research on the preparation of benzo[ c ]xanthones [11] .…”

Section: Introductionmentioning

confidence: 99%

“…Microwave (MW) irradiation has proven effective in enhancing the reaction rate, particularly in reactions that require high‐temperature and high‐pressure conditions [13] . Additionally, tandem reactions have emerged as an important tool for the preparation of complex natural products and biologically valuable molecules, as well as for the construction of carbon−carbon or carbon−heteroatom bonds [10f,14] . Previous studies also suggest the use of the versatile γ‐alkynyl groups of enynones for the preparation of substituted furans via the generation of allene and carbene intermediates under acidic, basic, or metal catalyst (Pd, Cu, Rh, or Zn) conditions (Scheme 1, d) [15] .…”

Section: Introductionmentioning

confidence: 99%

Metal‐Free, DBU‐Mediated, Microwave‐Assisted Synthesis of Benzo[c]xanthones by Tandem Reactions of Alkynyl‐1,3‐diketones

et al. 2020

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A base‐mediated, green, microwave‐assisted efficient preparation of a diverse benzoxanthone library from variety of readily accessible γ‐alkynyl 1,3‐diketones is reported. The synthesis is based on tandem reactions involving intramolecular cyclization, propargyl‐allenyl isomerization, and electrocyclization in one pot. Some of the benzoxanthones are also synthesized by the one‐pot reaction of 1,3‐diketone and alkynyl bromide under basic heating conditions. This transformation also results in the construction of one new C−C bond and one new C−O bond.

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Recent advances in the synthesis of xanthones and azaxanthones

Abstract: Xanthones are important O-heteroaromatic tricyclic molecules exhibiting a wide range of bioactivities and can represent a showcase to highlight recent techniques and strategies in organic synthesis towards lead discovery and...

Cited by 54 publications

References 243 publications

Xanthones Active against Multidrug Resistance and Virulence Mechanisms of Bacteria

Xanthones Active against Multidrug Resistance and Virulence Mechanisms of Bacteria

From Natural Products to New Synthetic Small Molecules: A Journey through the World of Xanthones

Metal‐Free, DBU‐Mediated, Microwave‐Assisted Synthesis of Benzo[c]xanthones by Tandem Reactions of Alkynyl‐1,3‐diketones

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