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Journal articles on the topic 'Synthesis of xanthone'

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Published: 5 June 2025

Last updated: 15 July 2025

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1

Paraskevas, Konstantinos, Christos Iliopoulos-Tsoutsouvas, Eleftheria A. Georgiou, and Ioannis K. Kostakis. "5-Chloro-6-oxo-6H-xantheno[4,3-d]thiazole-2-carbonitrile." Molbank 2022, no. 4 (2022): M1489. http://dx.doi.org/10.3390/m1489.

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Xanthones and benzothiazoles are important classes of heterocyclic compounds with versatile biological activities. Herein, we describe a straightforward and scalable synthesis of 5-chloro-6-oxo-6H-xantheno[4,3-d]thiazole-2-carbonitrile, a thiazole-fused xanthone, via a six-step approach, using Appel’s salt for the synthesis of the thiazole ring. The thiazole-fused xanthone was fully characterized employing 1H and 13C NMR spectra, using direct and long-range heteronuclear correlation experiments (HMBC and HMQC).

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2

Lemos, Agostinho, Ana Sara Gomes, Joana B. Loureiro, et al. "Synthesis, Biological Evaluation, and In Silico Studies of Novel Aminated Xanthones as Potential p53-Activating Agents." Molecules 24, no. 10 (2019): 1975. http://dx.doi.org/10.3390/molecules24101975.

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Xanthone scaffold has been regarded as an attractive chemical tool in the search for bioactive molecules with antitumor activity, and in particular two xanthone derivatives, 12-hydroxy-2,2-dimethyl-3,4-dihydro-2H,6H-pyrano [3,2-b]xanthen-6-one (4) and 3,4-dimethoxy-9-oxo-9H-xanthene-1-carbaldehyde (5), were described as a murine double minute 2 (MDM2)-p53 inhibitor and a TAp73 activator, respectively. The xanthone 5 was used as a starting point for the construction of a library of 3,4-dioxygenated xanthones bearing chemical moieties of described MDM2-p53 inhibitors. Eleven aminated xanthones were successfully synthesized and initially screened for their ability to disrupt the MDM2-p53 interaction using a yeast cell-based assay. With this approach, xanthone 37 was identified as a putative p53-activating agent through inhibition of interaction with MDM2. Xanthone 37 inhibited the growth of human colon adenocarcinoma HCT116 cell lines in a p53-dependent manner. The growth inhibitory effect of xanthone 37 was associated with the induction of G1-phase cell cycle arrest and increased protein expression levels of p53 transcriptional targets. These results demonstrated the potential usefulness of coupling amine-containing structural motifs of known MDM2-p53 disruptors into a 3,4-dioxygenated xanthone scaffold in the design of novel and potent p53 activators with antitumor activity and favorable drug-like properties. Moreover, in silico docking studies were performed in order to predict the binding poses and residues involved in the potential MDM2-p53 interaction.

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3

Huang, Qing, Youyi Wang, Huaimo Wu, Man Yuan, Changwu Zheng, and Hongxi Xu. "Xanthone Glucosides: Isolation, Bioactivity and Synthesis." Molecules 26, no. 18 (2021): 5575. http://dx.doi.org/10.3390/molecules26185575.

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Xanthones are secondary metabolites found in plants, fungi, lichens, and bacteria from a variety of families and genera, with the majority found in the Gentianaceae, Polygalaceae, and Clusiaceae. They have a diverse range of bioactivities, including anti-oxidant, anti-bacterial, anti-malarial, anti-tuberculosis, and cytotoxic properties. Xanthone glucosides are a significant branch of xanthones. After glycosylation, xanthones may have improved characteristics (such as solubility and pharmacological activity). Currently, no critical review of xanthone glucosides has been published. A literature survey including reports of naturally occurring xanthone glucosides is included in this review. The isolation, structure, bioactivity, and synthesis of these compounds were all explored in depth.

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4

Singh, Dileep Kumar, та Mahendra Nath. "Synthesis and spectroscopic properties of β-triazoloporphyrin–xanthone dyads". Beilstein Journal of Organic Chemistry 11 (17 серпня 2015): 1434–40. http://dx.doi.org/10.3762/bjoc.11.155.

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A novel series of β-triazoloporphyrin–xanthone conjugates and xanthone-bridged β-triazoloporphyrin dyads has been synthesized in moderate to good yields through Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction of copper(II) 2-azido-5,10,15,20-tetraphenylporphyrin or zinc(II) 2-azidomethyl-5,10,15,20-tetraphenylporphyrin with various alkyne derivatives of xanthones in DMF containing CuSO4 and ascorbic acid at 80 °C. Furthermore, these metalloporphyrins underwent demetalation under acidic conditions to afford the corresponding free-base porphyrins in good to excellent yields. After successful spectroscopic characterization, these porphyrins have been evaluated for their photophysical properties. The preliminary results revealed a bathochromic shift in the UV–vis and fluorescence spectra of these porphyrin–xanthone dyads.

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5

Badiali, Camilla, Valerio Petruccelli, Elisa Brasili, and Gabriella Pasqua. "Xanthones: Biosynthesis and Trafficking in Plants, Fungi and Lichens." Plants 12, no. 4 (2023): 694. http://dx.doi.org/10.3390/plants12040694.

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Xanthones are a class of secondary metabolites produced by plant organisms. They are characterized by a wide structural variety and numerous biological activities that make them valuable metabolites for use in the pharmaceutical field. This review shows the current knowledge of the xanthone biosynthetic pathway with a focus on the precursors and the enzymes involved, as well as on the cellular and organ localization of xanthones in plants. Xanthone biosynthesis in plants involves the shikimate and the acetate pathways which originate in plastids and endoplasmic reticulum, respectively. The pathway continues following three alternative routes, two phenylalanine-dependent and one phenylalanine-independent. All three routes lead to the biosynthesis of 2,3′,4,6-tetrahydroxybenzophenone, which is the central intermediate. Unlike plants, the xanthone core in fungi and lichens is wholly derived from polyketide. Although organs and tissues synthesizing and accumulating xanthones are known in plants, no information is yet available on their subcellular and cellular localization in fungi and lichens. This review highlights the studies published to date on xanthone biosynthesis and trafficking in plant organisms, from which it emerges that the mechanisms underlying their synthesis need to be further investigated in order to exploit them for application purposes.

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6

Mkounga, Pierre, Zacharias T. Fomum, Michèle Meyer, Bernard Bodo, and Augustin E. Nkengfack. "Globulixanthone F, a New Polyoxygenated Xanthone with an Isoprenoid Group and Two Antimicrobial Biflavonoids from the Stem Bark of Symphonia Globulifera¶." Natural Product Communications 4, no. 6 (2009): 1934578X0900400. http://dx.doi.org/10.1177/1934578x0900400613.

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Bioassay-guided fractionation of the stem bark of Symphonia globulifera has yielded three known xanthones, ugaxanthone (1), mbarraxanthone (2) and gentisein (3), two biflavonoid derivatives named GB2 (4) and manniflavanone GB3 (5), and one new polyoxygenated xanthone with an isoprenoid group, named globulixanthone F (6). The structures of these compounds were elucidated by means of spectroscopic methods. The spectral data of 1 and 2 are reported here for the first time, as well as the antimicrobial activity of globulixanthone F against a range of microorganisms. We also report the total synthesis of the xanthone skeleton.

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7

Bornadiego, Ana, Jesús Díaz, and Carlos F. Marcos. "Expeditious Multicomponent Synthesis of Xanthone Dimers." Proceedings 9, no. 1 (2018): 13. http://dx.doi.org/10.3390/ecsoc-22-05766.

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Xanthones are a type of compound widely found in many natural products from plants, fungi, and lichens and are considered privileged structures. Frequently, xanthones occur in nature as dimers, which often exhibit singular and potent biological effects. Although diverse methods for the synthesis of monomeric xanthones are known, dimeric xanthones remain synthetically challenging targets. Reported syntheses of dimeric xanthones are very scarce, and invariably involve a large number of synthetic steps. We have recently developed a multicomponent synthesis of xanthones starting from 3-carbonylchromones, isocyanides, and dienophiles. Here we report a similar one-pot tandem procedure, involving a [4+1]-[4+2] cycloaddition, that readily affords dimeric xanthones and dihydroxanthones, which are structurally similar to bioactive ergochromes.

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8

Pinto, Madalena M. M., Andreia Palmeira, Carla Fernandes, et al. "From Natural Products to New Synthetic Small Molecules: A Journey through the World of Xanthones." Molecules 26, no. 2 (2021): 431. http://dx.doi.org/10.3390/molecules26020431.

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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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9

Borzdziłowska, Paulina, and Ilona Bednarek. "Xanthones as natural compounds with a wide spectrum of biological activity." Postępy Higieny i Medycyny Doświadczalnej 72 (August 27, 2018): 767–80. http://dx.doi.org/10.5604/01.3001.0012.3277.

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One of the fields of research involving new substances with potential therapeutic effects is folk medicine. In indigenous cultures, including Far Eastern culture, medicine is based on beliefs and superstitions, passed down from generation to generation, concerning the effects of certain substances contained in plants, herbs or spices. Science very often uses traditional knowledge as a source of information. Observation of everyday life and customs of this culture became the starting point for this research on the plants of the family Clusiacaceae Lindl. Substances included in the different parts of these plants are used as anti-inflammatory, antipyretic, antiparasitic, antimicrobial, antifungal and anti-cancer drugs. Many studies have led to the isolation of compounds with different properties and uses, called xanthones. It is an interesting group which can be divided into natural and synthetic xanthone derivatives. On the other hand, xanthones are divided by the chemical structure and chemical ring synthesis. Many new xanthone derivatives are produced to evaluate the dependence of biological activity on the przeciwpasożytnichemical structure of these compounds. The most popular natural xanthones are α-mangostin and gambogic acid. Xanthones are tested in various aspects, but their most important feature is their strong antitumor activity. The distinct mechanism of action of xanthone derivatives and the limited number of side effects give great hope for the use of xanthones in anticancer therapy, as monotherapy drugs or as substances that support current chemotherapy.

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10

Bedi, Pooja, Richa Gupta, Richa Gupta, Tanay Pramanik, and Tanay Pramanik. "SYNTHESIS AND BIOLOGICAL PROPERTIES OF PHARMACEUTICALLY IMPORTANT XANTHONES AND BENZOXANTHONE ANALOGS: A BRIEF REVIEW." Asian Journal of Pharmaceutical and Clinical Research 11, no. 2 (2018): 12. http://dx.doi.org/10.22159/ajpcr.2018.v11i2.22426.

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Xanthones are one of the biggest classes of compounds in natural product chemistry. A number of xanthones have been isolated from natural sources of higher plants such as fungi, ferns, and lichens. Synthetic analogs of xanthones have shown a large number of pharmacological properties such as antioxidant, anti-inflammatory, antidiabetics, antihistamine, antitumoral, antiulcer, and algicidal. Moreover, they also find usages in photodynamic therapy, laser technology, and dyes. This review lays stress on various solvents, catalyst and synthetic route for synthesis of xanthones, benzoxanthones analogs. The review has also focused on the classifications of xanthone as well as extensively studied biological properties of the xanthones and benzoxanthones analogs.

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11

Kurniawan, Yehezkiel Steven, Krisfian Tata Aneka Priyangga, Jumina, et al. "An Update on the Anticancer Activity of Xanthone Derivatives: A Review." Pharmaceuticals 14, no. 11 (2021): 1144. http://dx.doi.org/10.3390/ph14111144.

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The annual number of cancer deaths continues increasing every day; thus, it is urgent to search for and find active, selective, and efficient anticancer drugs as soon as possible. Among the available anticancer drugs, almost all of them contain heterocyclic moiety in their chemical structure. Xanthone is a heterocyclic compound with a dibenzo-γ-pyrone framework and well-known to have “privileged structures” for anticancer activities against several cancer cell lines. The wide anticancer activity of xanthones is produced by caspase activation, RNA binding, DNA cross-linking, as well as P-gp, kinase, aromatase, and topoisomerase inhibition. This anticancer activity depends on the type, number, and position of the attached functional groups in the xanthone skeleton. This review discusses the recent advances in the anticancer activity of xanthone derivatives, both from natural products isolation and synthesis methods, as the anticancer agent through in vitro, in vivo, and clinical assays.

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12

Zoi, Ourania G., Trias N. Thireou, Vagelis E. Rinotas, et al. "Designer Xanthone." Journal of Biomolecular Screening 18, no. 9 (2013): 1092–102. http://dx.doi.org/10.1177/1087057113492335.

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Glutathione transferases (GSTs) are cell detoxifiers involved in multiple drug resistance (MDR), hampering the effectiveness of certain anticancer drugs. To our knowledge, this is the first report on well-defined synthetic xanthones as GST inhibitors. Screening 18 xanthones revealed three derivatives bearing a bromomethyl and a methyl group (7) or two bromomethyl groups (8) or an aldehyde group (17), with high inhibition potency (>85%), manifested by low IC50 values (7: 1.59 ± 0.25 µM, 8: 5.30 ± 0.30 µM, and 17: 8.56 ± 0.14 µM) and a competitive modality of inhibition versus CDNB (Ki(7) = 0.76 ± 0.18 and Ki(17) = 1.69 ± 0.08 µM). Of them, derivative 17 readily inhibited hGSTA1-1 in colon cancer cell lysate (IC50 = 10.54 ± 2.41 µM). Furthermore, all three derivatives were cytotoxic to Caco-2 intact cells, with 17 being the least cytotoxic (LC50 = 151.3 ± 16.3 µM). The xanthone scaffold may be regarded as a pharmacophore for hGSTA1-1 and the three derivatives, especially 17, as potent precursors for the synthesis of new inhibitors and conjugate prodrugs for human GSTs.

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13

Evangelista, E. A., M. R. C. Couri, R. B. Alves, D. S. Raslan, and R. P. F. Gil. "Microwave‐Assisted Xanthone Synthesis." Synthetic Communications 36, no. 16 (2006): 2275–80. http://dx.doi.org/10.1080/00397910600639653.

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14

Amanatie, Amanatie, Jumina Jumina, Mustofa Mustofa, and M. Hanafi. "SINTESIS XANTON DARI ASAM 2-PHENOXYBENZOIC ACID SEBAGAI BAHAN DASAR OBAT MALARIA BARU." Jurnal Kimia Terapan Indonesia 15, no. 2 (2013): 25–34. http://dx.doi.org/10.14203/jkti.v15i2.108.

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Synthesis of xanthone was conducted from the raw material of 2-phenoxybenzoic acid through acid-catalyzed-cyclization. The product was characterized using UV- Vis, 1 13 d FT-IR, H-NMR, C-NMR, an LC-MS Cyclization of 2-phenoxybenzoic acid using sulfuric acid catalyt gave xanthone in 86.11 % yield. These compounds as the basis of new malaria drugs.Keywords 2-phenoxybenzoic acid, Synthesis, Xanthone, Characterized.

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15

Szkaradek, Natalia, Daniel Sypniewski, Dorota Żelaszczyk, et al. "Influence of New Synthetic Xanthones on the Proliferation and Migration Potential of Cancer Cell Lines In Vitro." Anti-Cancer Agents in Medicinal Chemistry 19, no. 16 (2020): 1949–65. http://dx.doi.org/10.2174/1871520619666190405113519.

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Background: Natural plant metabolites and their semisynthetic derivatives have been used for years in cancer therapy. Xanthones are oxygenated heterocyclic compounds produced as secondary metabolites by higher plants, fungi or lichens. Xanthone core may serve as a template in the synthesis of many derivatives that have broad biological activities. Objective: This study synthesized a series of 17 new xanthones, and their anticancer potential was also evaluated. Methods: The anticancer potential was evaluated in vitro using a highly invasive T24 cancer cell line. Direct cytotoxic effects of the xanthones were established by IC50 estimation based on XTT assay. Results: 5 compounds of the total 17 showed significant cytotoxicity toward the studied cancer cultures and were submitted to further detailed analysis, including studies examining their influence on gelatinase A and B expression, as well as on the cancer cells migration and adhesion to an extracellular matrix. These analyses were carried out on five human tumor cell lines: A2780 (ovarian cancer), A549 (lung cancer), HeLa (cervical cancer), Hep G2 (liver cancer), and T24 (urinary bladder cancer). All the compounds, especially 4, showed promising anticancer activity: they exhibited significant cytotoxicity towards all the evaluated cell lines, including MCF-7 breast cancer, and hindered migration-motility activity of cancer cells demonstrating more potent activity than α-mangostin which served as a reference xanthone. Conclusion: These results suggest that our xanthone derivatives may be further analyzed in order to include them in cancer treatment protocols.

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16

Ribeiro, João, Cláudia Veloso, Carla Fernandes, Maria Elizabeth Tiritan, and Madalena M. M. Pinto. "Carboxyxanthones: Bioactive Agents and Molecular Scaffold for Synthesis of Analogues and Derivatives." Molecules 24, no. 1 (2019): 180. http://dx.doi.org/10.3390/molecules24010180.

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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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17

SOMAN, S. S., and K. N. TRIVEDI. "ChemInform Abstract: Synthesis of Xanthones. Part 11. Synthesis of 4-Methylpyrano[2,3-b]xanthone." ChemInform 29, no. 17 (2010): no. http://dx.doi.org/10.1002/chin.199817154.

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18

Aguila-Muñoz, Dolores G., Gabriel Vázquez-Lira, Erika Sarmiento-Tlale та ін. "Synthesis and Molecular Docking Studies of Alkoxy- and Imidazole-Substituted Xanthones as α-Amylase and α-Glucosidase Inhibitors". Molecules 28, № 10 (2023): 4180. http://dx.doi.org/10.3390/molecules28104180.

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Current antidiabetic drugs have severe side effects, which may be minimized by new selective molecules that strongly inhibit α-glucosidase and weakly inhibit α-amylase. We have synthesized novel alkoxy-substituted xanthones and imidazole-substituted xanthones and have evaluated them for their in silico and in vitro α-glucosidase and α-amylase inhibition activity. Compounds 6c, 6e, and 9b promoted higher α-glucosidase inhibition (IC50 = 16.0, 12.8, and 4.0 µM, respectively) and lower α-amylase inhibition (IC50 = 76.7, 68.1, and >200 µM, respectively) compared to acarbose (IC50 = 306.7 µM for α-glucosidase and 20.0 µM for α-amylase). Contrarily, derivatives 10c and 10f showed higher α-amylase inhibition (IC50 = 5.4 and 8.7 µM, respectively) and lower α-glucosidase inhibition (IC50 = 232.7 and 145.2 µM, respectively). According to the structure–activity relationship, attaching 4-bromobutoxy or 4′-chlorophenylacetophenone moieties to the 2-hydroxy group of xanthone provides higher α-glucosidase inhibition and lower α-amylase inhibition. In silico studies suggest that these scaffolds are key in the activity and interaction of xanthone derivatives. Enzymatic kinetics studies showed that 6c, 9b, and10c are mainly mixed inhibitors on α-glucosidase and α-amylase. In addition, drug prediction and ADMET studies support that compounds 6c, 9b, and 10c are candidates with antidiabetic potential.

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19

Rech, Jakub, Dorota Żelaszczyk, Henryk Marona, Agnieszka Gunia-Krzyżak, Paweł Żmudzki та Ilona Anna Bednarek. "Hyperthermia Intensifies α-Mangostin and Synthetic Xanthones’ Antimalignancy Properties". International Journal of Molecular Sciences 25, № 16 (2024): 8874. http://dx.doi.org/10.3390/ijms25168874.

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In order to improve naturally occurring xanthones’ anticancer properties, chemical synthesis is proposed. In this study, from eight novel xanthone derivatives coupled to morpholine or aminoalkyl morpholine, only the two most active ones were chosen. For additional enhancement of the anticancer activity of our tested compounds, we combined chemotherapy with hyperthermia in the range of 39–41 °C, from which the mild conditions of 39 °C were the most influencing. This approach had a profound impact on the anticancer properties of the tested compounds. TOV-21G and SC-OV-3 ovarian cell line motility and metastasis behavior were tested in native and hyperthermia conditions, indicating decreased wound healing properties and clonogenic activity. Similarly, the expression of genes involved in metastasis was hampered. The expression of heat shock proteins involved in cancer progression (Hsc70, HSP90A, and HSP90B) was significantly influenced by xanthone derivatives. Chemotherapy in mild hyperthermia conditions had also an impact on decreasing mitochondria potential, visualized with JC-1. Synthetic xanthone ring modifications may increase the anticancer activity of the obtained substances. Additional improvement of their activity can be achieved by applying mild hyperthermia conditions. Further development of a combined anticancer therapy approach may result in increasing currently known chemotherapeutics, resulting in a greater recovery rate and diminishment of the cytotoxicity of drugs.

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20

Chandra, Kanta Ghosh. "Synthesis of xanthones from chromones." Journal of Indian Chemical Society Vol. 90, Oct 2013 (2013): 1721–36. https://doi.org/10.5281/zenodo.5791878.

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Organic Chemistry Laboratory, Department of Biochemistry, Calcutta University, Kolkata-700 019, India <em>E-mail </em>: ghosh.chandrakanta@gmail.com <em>Manuscript received 03 June 2013, accepted 06 June 2013</em> Synthesis of xanthones from chromones published till 2012 is reviewed.

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KIMURA, MICHIO, and ICHIZO OKABAYASHI. "Spirolactones of xanthene. IV New method of xanthone synthesis by oxidation of novel spirolactones of dibenzo[c,h]xanthene and xanthenes." CHEMICAL & PHARMACEUTICAL BULLETIN 35, no. 1 (1987): 136–41. http://dx.doi.org/10.1248/cpb.35.136.

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22

Wei, Xiong, Danlin Liang, Qing Wang, Xiangbao Meng, and Zhongjun Li. "Total synthesis of mangiferin, homomangiferin, and neomangiferin." Organic & Biomolecular Chemistry 14, no. 37 (2016): 8821–31. http://dx.doi.org/10.1039/c6ob01622g.

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23

Santos, Clementina M. M., Diana C. G. A. Pinto, Vera L. M. Silva, and Artur M. S. Silva. "Arylxanthones and arylacridones: a synthetic overview." Pure and Applied Chemistry 88, no. 6 (2016): 579–94. http://dx.doi.org/10.1515/pac-2016-0407.

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AbstractArylxanthones and arylacridones although not yet found in nature are becoming an important group of heterocyclic compounds due to their promising biological activities. Their central cores, xanthone and acridone, are recognized as interesting motifs for drug development mainly to be used in antitumour chemotherapy. The synthesis of this type of compounds is still scarce but several successful examples were recently published and a large variety of arylated xanthone and acridone derivatives were prepared. A systematic survey of the literature dedicated to their synthesis will be presented and discussed in this review.

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24

Elix, JA, and VJ Portelli. "A Synthesis of the Lichen Xanthone Thiomelin." Australian Journal of Chemistry 43, no. 10 (1990): 1773. http://dx.doi.org/10.1071/ch9901773.

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25

Song, Gao-peng, Su-mei Li, Hong-zong Si, et al. "Synthesis and bioactivity of novel xanthone and thioxanthone l-rhamnopyranosides." RSC Advances 5, no. 45 (2015): 36092–103. http://dx.doi.org/10.1039/c5ra02846a.

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Bachman, James L., P. Rogelio Escamilla, Alexander J. Boley, Cyprian I. Pavlich, and Eric V. Anslyn. "Improved Xanthone Synthesis, Stepwise Chemical Redox Cycling." Organic Letters 21, no. 1 (2018): 206–9. http://dx.doi.org/10.1021/acs.orglett.8b03661.

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27

Lin, Chun-Nan, Hsin-Kaw Hsieh, Shiou-Jyh Liou, et al. "Synthesis and Antithrombotic Effect of Xanthone Derivatives." Journal of Pharmacy and Pharmacology 48, no. 9 (1996): 887–90. http://dx.doi.org/10.1111/j.2042-7158.1996.tb05994.x.

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28

Hoppmann, Christian, Ulrike Alexiev, Elisabeth Irran, and Karola Rück-Braun. "Synthesis and fluorescence of xanthone amino acids." Tetrahedron Letters 54, no. 34 (2013): 4585–87. http://dx.doi.org/10.1016/j.tetlet.2013.06.113.

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29

Verhé, R., L. De Buyck, N. De Kirape, W. De Wispelaere, and N. Schamp. "Facile synthesis of dihydrobenzo[a]xanthone derivatives." Bulletin des Sociétés Chimiques Belges 89, no. 1 (2010): 57–65. http://dx.doi.org/10.1002/bscb.19800890108.

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30

Alves, Ana, Marta Correia-da-Silva, Claúdia Nunes, et al. "Discovery of a New Xanthone against Glioma: Synthesis and Development of (Pro)liposome Formulations." Molecules 24, no. 3 (2019): 409. http://dx.doi.org/10.3390/molecules24030409.

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Following our previous work on the antitumor activity of acetylated flavonosides, a new acetylated xanthonoside, 3,6-bis(2,3,4,6-tetra-O-acetyl-β-glucopyranosyl)xanthone (2), was synthesized and discovered as a potent inhibitor of tumor cell growth. The synthesis involved the glycosylation of 3,6-di-hydroxyxanthone (1) with acetobromo-α-d-glucose. Glycosylation with silver carbonate decreased the amount of glucose donor needed, comparative to the biphasic glycosylation. Xanthone 2 showed a potent anti-growth activity, with GI50 < 1 μM, in human cell lines of breast, lung, and glioblastoma cancers. Current treatment for invasive brain glioma is still inadequate and new agents against glioblastoma with high brain permeability are urgently needed. To overcome these issues, xanthone 2 was encapsulated in a liposome. To increase the well-known low stability of these drug carriers, a proliposome formulation was developed using the spray drying method. Both formulations were characterized and compared regarding three months stability and in vitro anti-growth activity. While the proliposome formulation showed significantly higher stability, it was at the expense of losing its biocompatibility as a drug carrier in higher concentrations. More importantly, the new xanthone 2 was still able to inhibit the growth of glioblastoma cells after liposome formulation.

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31

Li, Junqi, Mingyu Hu, and Shao Q. Yao. "Rapid Synthesis, Screening, and Identification of Xanthone- and Xanthene-Based Fluorophores Using Click Chemistry." Organic Letters 11, no. 14 (2009): 3008–11. http://dx.doi.org/10.1021/ol9010344.

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32

Liu, Jie, Hui Bao, Huailing Wang, et al. "Synthesis of xanthone derivatives and anti-hepatocellular carcinoma potency evaluation: induced apoptosis." RSC Advances 9, no. 70 (2019): 40781–91. http://dx.doi.org/10.1039/c9ra06408g.

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33

Matsumoto, Takashi, Yuuki Fujimoto, Kanae Takahashi, Ryouma Kobayashi, Haruhiko Fukaya, and Hikaru Yanai. "Anion-Accelerated Aromatic Oxy-Cope Rearrangement in Geranylation/Nerylation of Xanthone: Stereochemical Insights and Synthesis of Fuscaxanthone F." Synlett 31, no. 14 (2020): 1378–83. http://dx.doi.org/10.1055/s-0040-1707117.

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An efficient installation of a 3,7-dimethylocta-2,6-dien-1-yl (geranyl or neryl) side chain at the C(1) position of a xanthone core by utilizing an anion-accelerated aromatic oxy-Cope rearrangement is described. Experiments revealed that this uncommon rearrangement takes place in a stereospecific manner through a chair-like transition-state structure. An application to the syntheses of the natural xanthone fuscaxanthone F, possessing a geranyl side chain, and its neryl analogue is also described.

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34

Iresha, Muthia Rahayu, Jumina Jumina, Harno Dwi Pranowo, Eti Nurwening Sholikhah, and Faris Hermawan. "Synthesis, Cytotoxicity Evaluation and Molecular Docking Studies of Xanthyl-Cinnamate Derivatives as Potential Anticancer Agents." Indonesian Journal of Chemistry 22, no. 5 (2022): 1407. http://dx.doi.org/10.22146/ijc.76164.

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A new series of xanthyl-cinnamate hybrid compounds (4a-d) have been synthesized and screened through in vitro assay against four human cancer cell lines, i.e., HeLa, T47D, A549, and WiDr. The results revealed that xanthone hybridization with cinnamic acid increases the selectivity of the compounds with SI values of 2.75–209.03 compared to its parent oxygenated-xanthone. Compound 1,3-dihydroxyxanthen-6-yl cinnamate (4c) showed high cytotoxic activity against WiDr cell lines with an IC50 value of 39.57 µM. Molecular docking studies revealed the possible binding modes of all hybrid compounds with EGFR protein. A complex of 3,6-dihydroxyxanthen-1-yl cinnamate (4d)-EGFR, as the best binding model, exhibited higher predicted EGFR inhibitory activity than erlotinib and oxygenated-xanthone with a ΔG and Ki value of -35.02 kJ/mol and 0.74 µM, respectively. Compounds 4c and 4d were chosen as the most potent derivates from the study.

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35

Zhang, Shi-Jie, Zhi-Shan Ding, Fu-Sheng Jiang, et al. "Synthesis, anticancer evaluation and docking study of vadimezan derivatives with carboxyl substitution." Med. Chem. Commun. 5, no. 4 (2014): 512–20. http://dx.doi.org/10.1039/c3md00372h.

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36

Chi, Xiao-Qian, Cheng-Ting Zi, Hong-Mei Li, et al. "Design, synthesis and structure–activity relationships of mangostin analogs as cytotoxic agents." RSC Advances 8, no. 72 (2018): 41377–88. http://dx.doi.org/10.1039/c8ra08409b.

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37

Resende, Diana I. S. P., Patrícia Pereira-Terra, Joana Moreira, et al. "Synthesis of a Small Library of Nature-Inspired Xanthones and Study of Their Antimicrobial Activity." Molecules 25, no. 10 (2020): 2405. http://dx.doi.org/10.3390/molecules25102405.

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A series of thirteen xanthones 3–15 was prepared based on substitutional (appendage) diversity reactions. The series was structurally characterized based on their spectral data and HRMS, and the structures of xanthone derivatives 1, 7, and 8 were determined by single-crystal X-ray diffraction. This series, along with an in-house series of aminated xanthones 16–33, was tested for in-vitro antimicrobial activity against seven bacterial (including two multidrug-resistant) strains and five fungal strains. 1-(Dibromomethyl)-3,4-dimethoxy-9H-xanthen-9-one (7) and 1-(dibromomethyl)-3,4,6-trimethoxy-9H-xanthen-9-one (8) exhibited antibacterial activity against all tested strains. In addition, 3,4-dihydroxy-1-methyl-9H-xanthen-9-one (3) revealed a potent inhibitory effect on the growth of dermatophyte clinical strains (T. rubrum FF5, M. canis FF1 and E. floccosum FF9), with a MIC of 16 µg/mL for all the tested strains. Compounds 3 and 26 showed a potent inhibitory effect on two C. albicans virulence factors: germ tube and biofilm formation.

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38

Yang, Qian, Rui Wang, Jie Han, et al. "Photo-induced tandem cyclization of 3-iodoflavones with electron rich five-membered heteroarenes." RSC Advances 7, no. 68 (2017): 43206–11. http://dx.doi.org/10.1039/c7ra07793a.

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Vinyl radicals were generated from 3-iodoflavones and occurred tandem cyclizations to synthesis a broad variety of novel polycyclic xanthone frameworks in good yields under mild and environmentally reaction conditions.

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39

Mendioroz, Pamela, and Federico Ferrelli. "Sustainable hydrology through an Eco-friendly Xanthone-based approach in coating solutions." International Journal of Hydrology 8, no. 2 (2024): 52–53. http://dx.doi.org/10.15406/ijh.2024.08.00374.

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Traditional antifouling (AF) biocides have raised environmental concerns, prompting a search for sustainable alternatives. This study addresses this pressing issue by reviewing xanthone derivatives as promising candidates for environmentally friendly AF coatings, showcasing a balance between enhanced AF activity and minimal environmental impact. Furthermore, an innovative, scalable, and highly versatile methodology based on a green nanopalladium-supported catalyst on biochar is presented as an interesting alternative to synthesize diverse xanthone derivatives. This approach aligns with sustainable practices in organic synthesis and expands the repertoire of potential antifouling solutions.

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Malekpoor, Mina, Sajjad Gharaghani, Ali Sharifzadeh, Syied Nezamoddin Mirsattari, and Ahmad Reza Massah. "Synthesis and Antibacterial Evaluation of Novel Xanthone Sulfonamides." Journal of Chemical Research 39, no. 8 (2015): 433–37. http://dx.doi.org/10.3184/174751915x14373971129805.

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41

LIN, CHUN-NAN, MEI-ING CHUNG, SHIOU-JYH LIOU, TAI-HUA LEE, and JIP-PYANG WANG. "Synthesis and Anti-inflammatory Effects of Xanthone Derivatives." Journal of Pharmacy and Pharmacology 48, no. 5 (1996): 532–38. http://dx.doi.org/10.1111/j.2042-7158.1996.tb05969.x.

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42

Fonteneau, Nadia, Philippe Martin, Martine Mondon, Hervé Ficheux, and Jean-Pierre Gesson. "Synthesis of quinone and xanthone analogs of rhein." Tetrahedron 57, no. 44 (2001): 9131–35. http://dx.doi.org/10.1016/s0040-4020(01)00918-8.

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43

Fromentin, Yann, Philippe Grellier, Jean Duplex Wansi, Marie-Christine Lallemand, and Didier Buisson. "Yeast-Mediated Xanthone Synthesis through Oxidative Intramolecular Cyclization." Organic Letters 14, no. 19 (2012): 5054–57. http://dx.doi.org/10.1021/ol302283p.

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44

Lin, Kai-Wei, Song-Chwan Fang, Chi-Feng Hung, et al. "Synthesis, Antiplatelet and Vasorelaxing Activities of Xanthone Derivatives." Archiv der Pharmazie 342, no. 1 (2009): 19–26. http://dx.doi.org/10.1002/ardp.200800002.

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45

ELIX, J. A., and V. J. PORTELLI. "ChemInform Abstract: Synthesis of the Lichen Xanthone Thiomelin." ChemInform 22, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.199103337.

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46

Amanatie, Amanatie, Jumina Jumina, Mustofa Mustofa, Hanafi M, La Ode Kadidae, and Sahidin I. "SYNTHESIS OF 2-HIDROXYXANTHONE FROM XANTHONE AS A BASIC MATERIAL FOR NEW ANTIMALARIAL DRUGS." Asian Journal of Pharmaceutical and Clinical Research 10, no. 12 (2017): 242. http://dx.doi.org/10.22159/ajpcr.2017.v10i12.19858.

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Objective: The purpose of this research is to synthesize 2-hydroxyxanthone from xanthone and to evaluate its antiplasmodial activity.Methods: The synthesis of 2-hydroxyxanthone followed the sequence of these synthetic stages, namely: 2-nitroxanthone, 2-aminoxanthone, and 2-hydroxyxanthone. The products were separated by chromatography methods including thin layer chromatography and vacuum liquid chromatography. Compound structures of the isolated products were determined based on their infrared and nuclear magnetic resonance spectra. To support these findings, the spectra were also matched to the corresponding data from literatures. The biological properties of the synthetic compound were evaluated toward Plasmodium falciparum 3D7.Results: 2-nitroxanthone was obtained as a brownish-yellow crystal in 69.00% yield with Madhya Pradesh of 181°C. Reduction of 2-nitroxanthone using SnCl2.2H2O/hydrogen chloride produced 2-aminoxanthone as a pale-yellow solid in 60.60% yield. Finally, the desired 2-hydroxyxanthone was achieved by initially reacting 2-aminoxanthone with sodium nitride to produce diazonium salt. Then, hydrolysis of the salt yielded 2-hydroxyxanthone as a white solid in 69.81% yield. Synthesis of 2-hydroxyxanthone from xanthone had an overall yield of38.35%. In vitro antiplasmodial assay against P. falciparum 3D7 showed that the half maximal inhibitory concentration value was 0.44 μg/mL.Conclusions: An antimalarial compound (2-hydroxyxanthone) was successfully synthesized from xanthone in three steps of synthetic reactions, i.e., the formation of 2-nitroxanthone, 2-aminoxanthone, and 2-hydroxyxanthone.

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Franceschin, Marco, Daniele Nocioni, Annamaria Biroccio, et al. "Design and synthesis of a new dimeric xanthone derivative: enhancement of G-quadruplex selectivity and telomere damage." Org. Biomol. Chem. 12, no. 47 (2014): 9572–82. http://dx.doi.org/10.1039/c4ob01658k.

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48

Ghosh, Krishna Kanta, Yun-Mi Jeong, Nam-Young Kang, et al. "The development of a nucleus staining fluorescent probe for dynamic mitosis imaging in live cells." Chemical Communications 51, no. 45 (2015): 9336–38. http://dx.doi.org/10.1039/c5cc02295a.

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The rapid and efficient synthesis of a novel fluorescent xanthone library (AX) and its application for the development of a new nucleus staining fluorescent probe (CDb12) for monitoring real-time mitosis progression in live cells is presented.

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Veríssimo, Ana C. S., Diana C. G. A. Pinto, and Artur M. S. Silva. "Marine-Derived Xanthone from 2010 to 2021: Isolation, Bioactivities and Total Synthesis." Marine Drugs 20, no. 6 (2022): 347. http://dx.doi.org/10.3390/md20060347.

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Marine life has proved to be an invaluable source of new compounds with significant bioactivities, such as xanthones. This review summarizes the advances made in the study of marine-derived xanthones from 2010 to 2021, from isolation towards synthesis, highlighting their biological activities. Most of these compounds were isolated from marine-derived fungi, found in marine sediments, and associated with other aquatic organisms (sponge and jellyfish). Once isolated, xanthones have been assessed for different bioactivities, such as antibacterial, antifungal, and cytotoxic properties. In the latter case, promising results have been demonstrated. Considering the significant bioactivities showed by xanthones, efforts have been made to synthesize these compounds, like yicathins B and C and the secalonic acid D, through total synthesis.

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Chen, Xing, Jing Leng, K. P. Rakesh, et al. "Synthesis and molecular docking studies of xanthone attached amino acids as potential antimicrobial and anti-inflammatory agents." MedChemComm 8, no. 8 (2017): 1706–19. http://dx.doi.org/10.1039/c7md00209b.

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