Chiral Derivatives of Xanthones with Antimicrobial Activity

Araújo, Joana; Fernandes, Carla; Pinto, Madalena; Tiritan, Maria Elizabeth

doi:10.3390/molecules24020314

Cited by 34 publications

(20 citation statements)

References 98 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As previously reported by Araújo et al [74], mangiferin derivatives present a large spectrum of antimicrobial activities. Singh et al [75,76] developed new mangiferin derivatives 22 – 27 (Figure 4) and screened their antipyretic and antimicrobial activities.…”

Section: Synthetic Chiral Derivatives Of Xanthonessupporting

confidence: 61%

“…One of the most studied xanthones found in Nature is α-mangostin, isolated from tropical fruits of Garcinia mangostana which have been used for centuries in folk medicine to treat many conditions [ 87 , 88 ]. Several studies have reported its anticancer and antimicrobial activities, among others, which have prompted researchers all over the world to synthesize diverse derivatives [ 74 , 87 , 88 , 89 , 90 , 91 , 92 , 93 , 94 ].…”

Section: Synthetic Chiral Derivatives Of Xanthonesmentioning

confidence: 99%

See 1 more Smart Citation

Synthetic Chiral Derivatives of Xanthones: Biological Activities and Enantioselectivity Studies

et al. 2019

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Section: Synthetic Chiral Derivatives Of Xanthonessupporting

confidence: 61%

Section: Synthetic Chiral Derivatives Of Xanthonesmentioning

confidence: 99%

Synthetic Chiral Derivatives of Xanthones: Biological Activities and Enantioselectivity Studies

et al. 2019

Self Cite

View full text Add to dashboard Cite

show abstract

“…Another reason to work with CDXs was to enlarge chemical and biological spaces. In fact, despite the large structural multiplicity of bioactive xanthones, only a handful of synthetic chiral derivatives was reported [ 125 , 126 ]. Additionally, the CDXs were also obtained to achieve other purposes, such as to be used as analytical tools, as it will be covered at the end of this section.…”

Section: A Library Of Natural Mimetic Xanthones Looking For Biologmentioning

confidence: 99%

“…Thioxanthones are isosters of xanthones. Structurally, they are S -heterocycles with a dibenzo-γ-thiopyrone scaffold, being described as an important class of molecules for their diverse biological properties, particularly their antitumor activity [ 126 , 149 , 150 ]. Their tricyclic scaffolds and the biological activities profile have led to the definition of thioxanthones as privileged structures, similarly to what happens with xanthones [ 98 ].…”

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

Self Cite

View full text Add to dashboard Cite

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.

show abstract

“…Recently, ( S , S )‐Whelk‐O1 CSP revealed good enantioselective performance for a series of derivatives of xanthones having a chiral moiety, mainly for those comprising an aromatic ring linked to the stereogenic center 27,28 . Chiral derivatives of xanthones, isolated from natural sources as well as obtained by synthesis, are very interesting compounds comprising a broad range of biological/pharmacological activities 29,30 . The synthesis of chiral derivatives of this class of compounds as single enantiomers for biological assays and to perform enantioselectivity studies is one of the main aims of our group 31–34 .…”

Section: Introductionmentioning

confidence: 99%

Chiral derivatives of xanthones and benzophenones: Synthesis, enantioseparation, molecular docking, and tumor cell growth inhibition studies

Phyo¹,

Teixeira

Gonçalves

et al. 2021

Chirality

Self Cite

View full text Add to dashboard Cite

Liquid chromatography enantioseparation and determination of enantiomeric purity of synthetized xanthone and benzophenone derivatives comprising one or more chiral moieties are reported. High enantioselectivity and resolution were observed in (S,S)‐Whelk‐O1 chiral stationary phase (CSP) for the enantiomeric mixtures of compounds comprising an aromatic ring linked to the stereogenic center(s), with α values ranging from 1.35 to 4.15 and Rs values ranging from 2.22 to 13.87. Among all the tested enantiomeric mixtures, those comprising three chiral moieties positioned in the xanthone scaffold gave the best chromatographic results. Enantiomers comprising an alkyl chain linked to the stereogenic centers were enantioseparated on a Lux® Celullose‐2 CSP. For both CSPs, the elution was performed in polar organic mode. The enantiomeric ratio (e.r.) values were always higher than 99%. Additionally, assessment of chiral recognition mechanisms on (S,S)‐Whelk‐O1 CSP was performed by molecular docking approach, which are in accordance with the chromatographic parameters. The nature and number of chiral moieties in the central aromatic scaffold of either xanthone or benzophenone derivatives are proved to be crucial for enantiorecognition. The evaluation of the growth inhibition of human tumor cell lines revealed that (S,S)‐(+)‐5 was the most potent compound, with values of GI50 of 12.83 ± 2.09 μM for A375‐C5 melanoma, 12.40 ± 1.16 μM for MCF‐7 breast adenocarcinoma, and 13.06 ± 1.29 μM for NCI‐H460 non‐small cell lung cancer. In some cases, the growth inhibitory effects demonstrated to be dependent on the stereochemistry of the compounds.

show abstract

Chiral Derivatives of Xanthones with Antimicrobial Activity

Cited by 34 publications

References 98 publications

Synthetic Chiral Derivatives of Xanthones: Biological Activities and Enantioselectivity Studies

Synthetic Chiral Derivatives of Xanthones: Biological Activities and Enantioselectivity Studies

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

Chiral derivatives of xanthones and benzophenones: Synthesis, enantioseparation, molecular docking, and tumor cell growth inhibition studies

Contact Info

Product

Resources

About