529-49-7Relevant academic research and scientific papers
TWO NEW XANTHONE GLYCOSIDES FROM TRIPTEROSPERMUM LANCEOLATUM
Lin, Chun-Nan,Chang, Cheng-Hsiung,Arisawa, Munehisa,Shimizu, Mineo,Morita, Naokata
, p. 205 - 208 (1982)
Oleanolic acid, mangiferin, and two new xanthone glucosides, named lanceoside (1,8-dihydroxy-3,7-dimethoxyxanthone-4-O-β-D-glucoside) and lancerin (C-4-β-D-glucosyl-1,3,7-trihydroxyxanthone), respectively, were isolated from the aerial parts of Tripterospermum lanceolatum.Key Word Index - Tripterospermum lanceolatum; Gentianaceae; xanthone glucoside; lanceoside; 1,8-dihydroxy-3,7-dimethoxyxanthone-4-O-β-D-glucoside; lancerin; C-4-β-D-glucosyl-1,3,7-trihydroxyxanthone.
Donor compound as Xanthone-NO well as preparation method and application thereof in preparation of anti-tumor drugs (by machine translation)
-
Page/Page column 5; 6; 10; 11, (2020/01/04)
The invention belongs to the technical field of, antitumor drugs, and Xanthone - NO discloses a compound of formula I as well as a preparation method thereof, and an Xanthone - NO. application according to the: invention in preparation of an antitumor drug. In-flight vehicle, R1 , R2 , R3 The compound of the present invention is H, OH, Cl, Br prepared F;n＝2-8. from substituted salicylic acid and m-taminophen and then is prepared xanthones, from the 1,n - substituted salicylic acid and the 3 - O - M xanthone,bromophenol to. prepare the compound of the, present invention for inhibiting the tumor cell proliferation in vitro and, inhibiting the apoptosis of tumor cells by multiple, targets. (by machine translation)
Incorporation of nitric oxide donor into 1,3-dioxyxanthones leads to synergistic anticancer activity
Liu, Jie,Zhang, Cao,Wang, Huailing,Zhang, Lei,Jiang, Zhenlei,Zhang, Jianrun,Liu, Zhijun,Chen, Heru
, p. 158 - 172 (2018/04/05)
Fifty 1,3-dioxyxanthone nitrates (4a ～ i-n, n = 1–6) were designed and synthesized based on molecular similarity strategy. Incorporation of nitrate into 1,3-dioxyxanthones with electron-donating groups at 6–8 position brought about synergistic anticancer effect. Among them, compound 4g-4 was confirmed the most active agent against HepG-2 cells growth with an IC50 of 0.33 ± 0.06 μM. It dose-dependently increased intramolecular NO levels. This activity was attenuated by either NO scavenger PTIO or mitochondrial aldehyde dehydrogenase (mtADH) inhibitor PCDA. Apoptosis analysis indicated different contributions of early/late apoptosis and necrosis to cell death for different dose of 4g-4. 4g-4 arrested more cells on S phase. Results from Western Blot implied that 4g-4 regulated p53/MDM2 to promote cancer cell apoptosis. All the evidences support that 4g-4 is a promising anti-cancer agent.
Synthesis and antitumor, antityrosinase, and antioxidant activities of xanthone
Zhou, Bei-Dou,Zeng, Li-Lan,Tong, Yu-Gui,Fang, Jia-Ying,Ruan, Zhi-Peng,Zeng, Xiao-Yun,Fang, Yuan-Yuan,Xu, Gui-Fen,Hu, Dong-Bao
, p. 467 - 476 (2018/04/05)
Ten substituted 1,3-dihydroxyxanthones were synthesized in one step. The yields ranged from 40 to 76%. Compounds 8–10 were first reported. Next, the compounds’ in vitro anti-proliferative activities against nine human cancer cell lines, antityrosinase, and antioxidant activities were evaluated. Compounds 1, 4, 6–7, and 9–10 exhibited enhanced cytotoxicity against certain cancer cells. Compounds 2, 8, 9, and 10 inhibited tyrosinase activity to a certain extent. In addition, compound 4 exhibited the best antioxidant activity, which was consistent with theoretical calculations. These results demonstrated that compounds 1–2, 4, and 6–10 were promising leads for further investigation.
Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them
Liu, Jie,Zhang, Jianrun,Wang, Huailing,Liu, Zhijun,Zhang, Cao,Jiang, Zhenlei,Chen, Heru
, p. 50 - 61 (2017/04/06)
34 Xanthones were synthesized by microwave assisted technique. Their in?vitro inhibition activities against five cell lines growth were evaluated. The SAR has been thoroughly discussed. 7-Bromo-1,3-dihydroxy-9H-xanthen-9-one (3-1) was confirmed as the most active agent against MDA-MB-231?cell line growth with an IC50 of 0.46?±?0.03?μM. Combination of 3-1 and 5,6-dimethylxanthone-4-acetic acid (DMXAA) showed the best synergistic effect. Apoptosis analysis indicated different contributions of early/late apoptosis and necrosis to cell death for both monomers and the combination. Western Blot implied that the combination regulated p53/MDM2 to a better healthy state. Furthermore, 3-1 and DMXAA arrested more cells on G2/M phase; while the combination arrested more cells on S phase. All the evidences support that the 3-1/DMXAA combination is a better anti-cancer therapy.
Microwave-assisted synthesis of xanthones promoted by ytterbium triflate
Genovese, Salvatore,Fiorito, Serena,Specchiulli, Maria Carmela,Taddeo, Vito Alessandro,Epifano, Francesco
supporting information, p. 847 - 850 (2015/01/30)
Xanthones represent a class of naturally occurring compounds with valuable and promising reported pharmacological activities. One of the main disadvantages in the use of such products is related to the difficulties in their chemical synthesis. In this Letter a new and improved method for the chemical synthesis of xanthones is described. The title compounds have been synthesized in good yields under microwave irradiation from substituted 2-hydroxybenzoic acids and phenols in the presence of Yb(OTf)3 hydrate as the catalyst.
An efficient and convenient microwave-assisted chemical synthesis of (thio)xanthones with additional in vitro and in silico characterization
Verbanac, Donatella,Jain, Subhash C.,Jain, Nidhi,Chand, Mahesh,?ip?i? Paljetak, Hana,Matija?i?, Mario,Peri?, Mihaela,Stepani?, Vi?nja,Saso, Luciano
experimental part, p. 3180 - 3185 (2012/07/14)
Xanthones and their thio-derivatives are a class of pleiotropic compounds with various reported pharmacological and biological activities. Although these activities are mainly determined in laboratory conditions, the class itself has a great potential to be utilized as promising chemical scaffold for the synthesis of new drug candidates. One of the main obstacles in utilization of these compounds was related to the difficulties in their chemical synthesis. Most of the known methods require two steps, and are limited to specific reagents not applicable to a large number of starting materials. In this paper a new and improved method for chemical synthesis of xanthones is presented. By applying a new procedure, we have successfully obtained these compounds with the desired regioselectivity in a shorter reaction time (50 s) and with better yield (>80%). Finally, the preliminary in vitro screenings on different bacterial species and cytotoxicity assessment, as well as in silico activity evaluation were performed. The obtained results confirm potential pharmacological use of this class of molecules.
Synthesis, SAR and biological evaluation of natural and non-natural hydroxylated and prenylated xanthones as antitumor agents
Zhang, Xiaojin,Li, Xiang,Tao, Lei,Gao, Yuan,Gong, Dandan,Xi, Meiyang,Xu, Xiaoli,Guo, Qinglong,You, Qidong,Ye, Suofu,Zhang, Yu,Meng, Huyan,Zhang, Mingqian,Gao, Wenlei
, p. 1012 - 1025,14 (2012/12/12)
In order to explore the detailed structure-activity relationship (SAR) around xanthone scaffold bearing hydroxyl and prenyl moieties, twenty-nine natural and non-natural hydroxylated and prenylated xanthones have been synthesized and evaluated for their in vitro anti-proliferative activities against five human cancer cell lines, including HepG2 (hepatocelluar carcinoma), HCT-116 (colon carcinoma), A549 (lung carcinoma), BGC823 (gastric carcinoma) and MDAMB- 231 (breast carcinoma). The SAR analysis revealed that the anti-proliferative activity of the xanthones is substantially influenced by the position and number of attached hydroxyl and prenyl groups, and the presence of hydroxyl group ortho to the carbonyl function of xanthone scaffold contributes significantly to their cytotoxicity. The new prenylated xanthone 20 with a relatively simple structure, namely 1,3,8-trihydroxy-2-prenylxanthone, was found to exhibit potent antitumor activities comparable to mangostin against all the five cancer cell lines. Further mechanistic studies suggested that compound 20 induces apoptosis and causes cell cycle arrest at S phase in HepG2 cells. These results have highlighted compound 20 as a new potential lead candidate for future development of novel potent broad-spectrum antitumor agents.
Facile synthesis of 1,3,7-trihydroxyxanthone and its regioselective coupling reactions with prenal: Simple and efficient access to osajaxanthone and nigrolineaxanthone F
Mondal, Mukulesh,Puranik, Vedavati G.,Argade, Narshinha P.
, p. 4992 - 4995 (2007/10/03)
A facile five-step synthesis of naturally occurring 1,3,7- trihydroxyxanthone has been described starting from 1,3,5-trimethoxybenzene via NBS-induced nuclear bromination, lithiation followed by an in situ benzoylation with methyl 2,5-dibenzyloxybenzoate, selective deprotection of the two benzyl groups, base-catalyzed intramolecular cyclization, and demethylations pathway with 62% overall yield. The regioselective coupling reactions of 1,3,7-trihydroxyxanthone with prenal in the presence of calcium hydroxide at room temperature and under thermal conditions at 140-150 °C have been demonstrated to exclusively obtain the natural products osajaxanthone in 15% yield and nigrolineaxanthone F in 98% yield, respectively.
Synthesis and pharmacological activities of xanthone derivatives as α-glucosidase inhibitors
Liu, Yan,Zou, Lan,Ma, Lin,Chen, Wen-Hua,Wang, Bo,Xu, Zun-Le
, p. 5683 - 5690 (2007/10/03)
Considerable interest has been attracted in xanthone and its derivatives because of their large variety of pharmacological activities. In this project, a series of hydroxylxanthones and their acetoxy and alkoxy derivatives were synthesized and evaluated a
