6052-93-3

Usage

InChI:InChI=1/C15H12F3NO2/c16-15(17,18)9-4-3-5-10(8-9)19-13(20)11-6-1-2-7-12(11)14(19)21/h1-5,8,11-12H,6-7H2

Upstream product

• 303-07-1 2,6-Dihydroxybenzoic acid 
• 108-46-3 recorcinol 
• 108-73-6 3,5-dihydroxyphenol 
• 3147-64-6 2-hydroxy-6-methoxybenzoic acid 
• 859779-91-2 1,3,8-triacetoxy-xanthene 
• 859967-89-8 xanthene-1,3,8-triol 
• 2150-45-0 methyl 2,6-dihydroxybenzoate 
• 82490-40-2 1,3,8-triacetoxyxanthone 

Downstream Products

• 2438637-65-9 3-chloro-N-(1,8-dihydroxy-9-oxo-9H-xanthen-3-yl)-2-fluorobenzenesulfonamide 

Relevant academic research and scientific papers

New chiral stationary phases for liquid chromatography based on small molecules: Development, enantioresolution evaluation and chiral recognition mechanisms

Recently, we reported the development of new chiral stationary phases (CSPs) for liquid chromatography (LC) based on chiral derivatives of xanthones (CDXs). Based on the most promising CDX selectors, 12 new CSPs were successfully prepared starting from suitable functionalized small molecules including xanthone and benzophenone derivatives. The chiral selectors comprising one, two, three, or four chiral moieties were covalently bonded to a chromatographic support and further packed into LC stainless-steel columns (150?×?2.1?mm I.D.). The enantioselective performance of the new CSPs was evaluated by LC using different classes of chiral compounds. Specificity for enantioseparation of some CDXs was observed in the evaluation of the new CSPs. Besides, assessment of chiral recognition mechanisms was performed by computational studies using molecular docking approach, which are in accordance with the chromatographic parameters. X-Ray analysis was used to establish a chiral selector 3D structure.

Imidazole-sulfonic-acid ionic liquid composition as well as preparation method and application thereof

The invention discloses an imidazole-sulfonic-acid ionic liquid composition as well as a preparation method and application thereof. The imidazole-sulfonic-acid ionic liquid composition is prepared through the following method comprising the following steps of heating imidazole-sulfonic-acid ionic liquid to 70 to 80 DEG C; adding phosphorus pentoxide into the ionic liquid prepared in the previousstep, sufficiently reacting at 80 to 100 DEG C, and removing a low-boiling-point substance under decompression, so as to obtain the transparent imidazole-sulfonic-acid ionic liquid composition. The ionic liquid composition prepared by the preparation method is applied to the synthesis of xanthone; reaction by-products are reduced; the ionic liquid can be recovered and recycled and the imidazole-sulfonic-acid ionic liquid composition has certain application value.

Synthesis and antitumor, antityrosinase, and antioxidant activities of xanthone

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.

The design and synthesis of n-xanthone benzenesulfonamides as novel phosphoglycerate mutase 1 (PGAM1) inhibitors

Upregulation of phosphoglycerate mutase 1 (PGAM1) has been identified as one common phenomenon in a variety of cancers. Inhibition of PGAM1 provides a new promising therapeutic strategy for cancer treatment. Herein, based on our previous work, a series of new N-xanthone benzenesulfonamides were discovered as novel PGAM1 inhibitors. The representative molecule 15h, with an IC50 of 2.1 μM, showed an enhanced PGAM1 inhibitory activity and higher enzyme inhibitory specificity compared to PGMI-004A, as well as a slightly improved antiproliferative activity.

Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them

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.

A bellidifodin preparing method

A bellidifodin preparing method is disclosed. The method includes preparing methanesulfonic acid and phosphorus pentoxide according to a ratio into a composite medium, adding 2,6-dihydroxybenzoic acid and phloroglucinol into the medium, performing a reaction to obtain 1,3,8-trihydroxy xanthenone, performing selective oxidation under alkaline conditions through using potassium persulfate to obtain 1,3,5,8-tetrahydroxy xanthenone, and subjecting the 1,3,5,8-tetrahydroxy xanthenone and iodomethane to methylation to obtain the target compound that is the bellidifodin. According to the method, reaction steps are shortened, reaction operation is simplified, the yield is increased and the method has certain application value.

Xanthone and Flavone Derivatives as Dual Agents with Acetylcholinesterase Inhibition and Antioxidant Activity as Potential Anti-Alzheimer Agents

Alzheimer's disease (AD) is a multifactorial neurodegenerative disorder that is associated with the elderly. The current therapy that is used to treat AD is based mainly on the administration of acetylcholinesterase (AChE) inhibitors. Due to their low eff

Anti-AIDS agents 85. Design, synthesis, and evaluation of 1R,2R-dicamphanoyl-3,3-dimethyldihydropyrano-[2,3-c]xanthen-7(1H)-one (DCX) derivatives as novel anti-HIV agents

In this study, 1R,2R-dicamphanoyl-3,3-dimethydihydropyrano[2,3-c]xanthen- 7(1H)-one (DCX) derivatives were designed and synthesized as novel anti-HIV agents against both wild-type and non-nucleoside reverse transcriptase (RT) inhibitor-resistant HIV-1 (RTMDR-1) strains. Twenty-four DCX analogs (6-29) were synthesized and evaluated against the non-drug-resistant HIV-1 NL4-3 strain, and selected analogs were also screened for their ability to inhibit the RTMDR-1 strain. Compared with the control 2-ethyl-3′,4′-di-O-(-)- camphanoyl-2′,2′-dimethyldihydropyrano[2,3-f]chromone (2-EDCP, 2), one of the best anti-HIV coumarin derivatives in our prior study, three DCX compounds (7, 12, and 22) showed better activity against both HIV strains with an EC50 range of 0.062-0.081 μM, and five additional compounds (8, 11, 16, 18, and 21) exhibited comparable anti-HIV potency. Six DCX analogs (7, 11-12, 18, and 21-22) also showed enhanced selectivity index (SI) values in comparison to the control. Structure-activity relationship (SAR) information suggested that the extended conjugated system of the pyranoxanthone skeleton facilitates the interaction of the small DCX molecule within the viral binding pocket, consequently leading to enhanced anti-HIV activity and selectivity. Compared to DCP compounds, DCX analogs are a more promising new class of anti-HIV agents.

An efficient and convenient microwave-assisted chemical synthesis of (thio)xanthones with additional in vitro and in silico characterization

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

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.