Synthesis and preliminary anti-inflammatory evaluation of xanthone derivatives

Żelaszczyk, Dorota; Lipkowska, Anna; Szkaradek, Natalia; Słoczyńska, Karolina; Gunia‐Krzyżak, Agnieszka; Librowski, Tadeusz; Marona, Henryk

doi:10.1515/hc-2017-0215

Cited by 7 publications

(6 citation statements)

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“…Recently, Zelaszczyk et al [ 140 ] synthesized two new chiral XAA derivatives 163 and 164 ( Figure 15 ) by the reaction of 3-hydroxyxanthone with ethyl 2-bromopropanoate, followed by ester hydrolysis [ 140 ]. These compounds were found to have anti-inflammatory and analgesic activities [ 34 , 140 ].…”

Section: Synthetic Chiral Derivatives Of Xanthonesmentioning

confidence: 99%

Synthetic Chiral Derivatives of Xanthones: Biological Activities and Enantioselectivity Studies

et al. 2019

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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.

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Section: Synthetic Chiral Derivatives Of Xanthonesmentioning

confidence: 99%

Synthetic Chiral Derivatives of Xanthones: Biological Activities and Enantioselectivity Studies

et al. 2019

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“…The synthesis of compounds 324 – 332 (Table 2) were reported in 1998, by Pickert et al [154], through the same synthetic pathway as described for compounds 276 – 281 . Recently, Zelaszczyk et al [175] synthesized carboxyxanthone derivatives 333 – 338 (Table 2) though derivatization of the previously described 3-hydroxyxanthones with sodium chloroacetate or ethyl 2-bromopropanoate followed by ester hydrolysis.…”

Section: Synthetic Carboxyxanthone Derivativesmentioning

confidence: 99%

“…Carboxyxanthone derivatives 321 and 320 were evaluated as antagonists of leukotriene B4 receptor [163]. Compounds 333 – 338 were tested for analgesic, anti-edema and ulcerogenic activities [175]. Both compounds 337 and 338 exhibited promising anti-inflammatory activity with compound 338 also showing excellent analgesic activity.…”

Section: Synthetic Carboxyxanthone Derivativesmentioning

confidence: 99%

Carboxyxanthones: Bioactive Agents and Molecular Scaffold for Synthesis of Analogues and Derivatives

et al. 2019

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Xanthones represent a structurally diverse group of compounds with a broad range of biological and pharmacological activities, depending on the nature and position of various substituents in the dibenzo-γ-pyrone scaffold. Among the large number of natural and synthetic xanthone derivatives, carboxyxanthones are very interesting bioactive compounds as well as important chemical substrates for molecular modifications to obtain new derivatives. A remarkable example is 5,6-dimethylxanthone-4-acetic acid (DMXAA), a simple carboxyxanthone derivative, originally developed as an anti-tumor agent and the first of its class to enter phase III clinical trials. From DMXAA new bioactive analogues and derivatives were also described. In this review, a literature survey covering the report on carboxyxanthone derivatives is presented, emphasizing their biological activities as well as their application as suitable building blocks to obtain new bioactive derivatives. The data assembled in this review intends to highlight the therapeutic potential of carboxyxanthone derivatives and guide the design for new bioactive xanthone derivatives.

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“…Xanthone derivatives have been subject of multidirectional research for many years. A lot of them have a favorable biological and pharmacological activity profile, including among other antioxidant [17], antimicrobial [18], anticancer [19,20], and anti-inflammatory effect [21]. Moreover, xanthone derivatives have also recently been of interest in the field of cosmetics chemistry.…”

Section: Introductionmentioning

confidence: 99%

“…Xanthone (dibenzo-γ-pyrone) possesses conjugated double b potential substitution positions. Coupling with an appropriate a additional chromophores gives the opportunity to select substan tended photoprotectiveness in a wide UV range but also with a sa Xanthone derivatives have been subject of multidirectional resear of them have a favorable biological and pharmacological activity p other antioxidant [17], antimicrobial [18], anticancer [19,20], and a [21]. Moreover, xanthone derivatives have also recently been of in metics chemistry.…”

Section: Introductionmentioning

confidence: 99%

The Involvement of Xanthone and (E)-Cinnamoyl Chromophores for the Design and Synthesis of Novel Sunscreening Agents

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Gunia‐Krzyżak

Słoczyńska

et al. 2020

IJMS

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Excessive UV exposure contributes to several pathological conditions like skin burns, erythema, premature skin aging, photodermatoses, immunosuppression, and skin carcinogenesis. Effective protection from UV radiation may be achieved with the use of sunscreens containing UV filters. Currently used UV filters are characterized by some limitations including systemic absorption, endocrine disruption, skin allergy induction, and cytotoxicity. In the research centers all over the world new molecules are developed to improve the safety, photostability, solubility, and absorption profile of new derivatives. In our study, we designed and synthesized seventeen novel molecules by combining in the structures two chromophores: xanthone and (E)-cinnamoyl moiety. The ultraviolet spectroscopic properties of the tested compounds were confirmed in chloroform solutions. They acted as UVB or UVA/UVB absorbers. The most promising compound 9 (6-methoxy-9-oxo-9H-xanthen-2-yl)methyl (E)-3-(2,4-dimethoxyphenyl)acrylate) absorbed UV radiation in the range 290–369 nm. Its photoprotective activity and functional photostability were further evaluated after wet milling and incorporation in the cream base. This tested formulation with compound 9 possessed very beneficial UV protection parameters (SPFin vitro of 19.69 ± 0.46 and UVA PF of 12.64 ± 0.32) which were similar as broad-spectrum UV filter tris-biphenyl triazine. Additionally, compound 9 was characterized by high values of critical wavelength (381 nm) and UVA/UVB ratio (0.830) thus it was a good candidate for broad-spectrum UV filter and it might protect skin against UVA-induced photoaging. Compound 9 were also shown to be photostable, non-cytotoxic at concentrations up to 50 µM when tested on five cell lines, and non-mutagenic in Ames test. It also possessed no estrogenic activity, according to the results of MCF-7 breast cancer model. Additionally, its favorable lipophilicity (miLogP = 5.62) does not predispose it to penetrate across the skin after topical application.

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Synthesis and preliminary anti-inflammatory evaluation of xanthone derivatives

Cited by 7 publications

References 26 publications

Synthetic Chiral Derivatives of Xanthones: Biological Activities and Enantioselectivity Studies

Synthetic Chiral Derivatives of Xanthones: Biological Activities and Enantioselectivity Studies

Carboxyxanthones: Bioactive Agents and Molecular Scaffold for Synthesis of Analogues and Derivatives

The Involvement of Xanthone and (E)-Cinnamoyl Chromophores for the Design and Synthesis of Novel Sunscreening Agents

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