40547-32-8

Usage

Chemical structure

1,3-Dihydroxy-6-methyl-9H-xanthen-9-one

Type of compound

Synthetic organic compound

Classification

Xanthene dye

Fluorescence

Bright yellow-green color when excited by light

Applications

a. Fluorescent tracer in biological and medical imaging
b. Chemical and environmental analysis
c. Production of colorants and inks
d. pH indicator

Toxicity

Low-toxicity compound when used in regulated amounts

Potential hazards

Excessive exposure can cause irritation to eyes, skin, and respiratory system

Upstream product

• 50-85-1 2-hydroxy-p-toluic acid 
• 108-46-3 recorcinol 
• 108-73-6 3,5-dihydroxyphenol 

Downstream Products

• 959316-03-1 acetic acid 3-acetoxy-6-[(4-fluoro-phenyl)-hydrazonomethyl]-9-oxo-9H-xanthen-1-yl ester 

Relevant academic research and scientific papers

Synthesis and antiproliferative activity of aryl- and heteroaryl-hydrazones derived from xanthone carbaldehydes

In order to explore the antiproliferative effect associated with the xanthone framework, several arylhydrazonomethyl derivatives were synthesized from various isomeric 1,3-dihydroxyxanthone carbaldehydes. Variation in the position of the aldehydic functio

Donor compound as Xanthone-NO well as preparation method and application thereof in preparation of anti-tumor drugs (by machine translation)

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

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 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.

Xanthones compounds and its antidepressant

The invention discloses xanthone compounds and their use in depression resistance. The xanthone compounds are compounds shown in the structural formula (I) or their pharmaceutically acceptable salts. An experiment proves that the xanthone compounds have good depression-resistant activity and a part of the xanthone compounds have depression-resistant activity superior to that of venlafaxine. Therefore, the xanthone compounds and their pharmaceutically acceptable salts can be used for preparation of depression-resistant drugs.

Synthesis and bioactivity of novel xanthone and thioxanthone l-rhamnopyranosides

A series of xanthone and thioxanthone rhamnopyranosides were designed and synthesized. Their in vitro cytotoxicity and topoisomerase inhibitory activity were evaluated. The bioassay results indicated that the introduction of the 2,3-di-O-acetyl-α-l-rhamno

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.

Identification of Xanthones as Selective Killers of Cancer Cells Overexpressing the ABC Transporter MRP1

Multidrug-resistance protein1 (MRP1) belongs to the ATP-binding cassette (ABC) transporter family. MRP1 mediates MDR (multidrug resistance) by causing drug efflux either by conjugation to glutathione (GSH) or by co-transport with free GSH (without covalen

(2-Arylhydrazonomethyl)-substituted xanthones as antimycotics: Synthesis and fungistatic activity against Candida species

A series of arylhydrazones derived from various 6,8-diacetoxy- or 6,8-dihydroxy-9-oxo-9H-xanthene carboxaldehydes were synthesized and evaluated for their in vitro antifungal properties against two human pathogenic yeasts (Candida albicans and C. krusei) according to a diffusion method. The activity was strongly dependent from the position of the (1-arylhydrazinyl-2-ylidene)methyl chain in the xanthone molecular skeleton. Compounds having the nitrogen side chain in the 4-position, with a further halogen substitution on the terminal phenyl ring showed fungistatic effects. Within this series, the 4-fluorophenylhydrazinyl derivative 13g exhibited the highest activity, particularly against C. krusei, with a greater efficacy than that of econazole, used as reference.