6563-47-9

Usage

Molecular structure

Xanthenes family

Functionality

Fluorescent whitening agent

Application

Textile and paper industry

Mechanism

Absorbs UV light and re-emits it as visible light

Additional uses

Inks, coatings, and plastics

Environmental impact

Toxic and harmful if not properly managed

Safety precautions

Handle with caution

Appearance

Brightening and fluorescent properties

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 877-22-5 3-methoxysalicylic acid 
• 1521-38-6 2,3-dimethoxybenzoic acid 
• 197508-40-0 N,N-Diethyl-2,4-diisopropoxy-6-(2-methoxy-phenoxy)-benzamide 
• 13052-77-2 sodium 2-methoxyphenolate 
• 197508-41-1 1,3-Diisopropoxy-5-methoxy-xanthen-9-one 

Downstream Products

• 74045-97-9 psorospermin 
• 667885-50-9 (3,5-bis-benzyloxy-1-methoxy-9-oxo-9H-xanthen-4-yl)-acetaldehyde 
• 667885-48-5 4-allyl-3,5-bis-benzyloxy-1-hydroxy-xanthen-9-one 
• 667885-49-6 4-allyl-3,5-bis-benzyloxy-1-methoxy-xanthen-9-one 
• 667885-53-2 3,5-Bis-benzyloxy-4-((2S,3R)-3-hydroxymethyl-3-methyl-oxiranylmethyl)-1-methoxy-xanthen-9-one 
• 667885-52-1 3,5-Bis-benzyloxy-4-((Z)-4-hydroxy-3-methyl-but-2-enyl)-1-methoxy-xanthen-9-one 
• 667885-51-0 4-(3,5-bis-benzyloxy-1-methoxy-9-oxo-9H-xanthen-4-yl)-2-methyl-but-2-enoic acid methyl ester 
• 667885-54-3 Methanesulfonic acid (2R,3S)-3-(3,5-bis-benzyloxy-1-methoxy-9-oxo-9H-xanthen-4-ylmethyl)-2-methyl-oxiranylmethyl ester 
• 26486-92-0 6-deoxyisojacareubin 
• 1448599-59-4 5-methoxy-3-(2-methylbut-3-yn-2-yloxy)-9-oxo-9H-xanthen-1-yl 4-methylbenzenesulfonate 
• 441004-78-0 11-methoxy-3,3-dimethyl-7-oxo-3,7-dihydropyrano[2,3-c]-xanthen-6-yl 4-methylbenzenesulfonate 

Relevant academic research and scientific papers

Sulfonated xanthones from Hypericum sampsonii

Two xanthones 1 and 2, together with nine known compounds were obtained from the whole plant of Hypericum sampsonii. This is the first report of sulfonated xanthonoids. Compounds 1 and 2 exhibited significant cytotoxicity to P388 cancer cell line. Xanthones, 1,3-dihydroxy-5-methoxyxanthone-4-sulfonate and 1,3-dihydroxy-5-O-β-d-glycopyranosylxanthone-4-sulfonate, together with nine known compounds were obtained from H. sampsonii. This is the first report of sulfonated xanthonoids. Furthermore, compounds 1 and 2 exhibited significant cytotoxicity against the P388 cancer cell line.

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 and biological evaluation of C1-O-substituted-3-(3-butylamino-2-hydroxy-propoxy)-xanthen-9-one as topoisomerase IIα catalytic inhibitors

Topoisomerase II poison blocks the transitorily generated DNA double-strand breaks (DSBs) from religation, thereby causes severe DNA damage and gene toxicity. While topoisomerase II catalytic inhibitor does not form cleavable DNA-enzyme complex because its function attributes to inhibition of the catalytic steps of the enzyme such as before generating DNA DSBs or in the last step of the catalytic cycle after religation. It has been reported that the stabilizing effect of etoposide on transient cleavable DNA-topoisomerase IIβ complex attributes to its secondary malignancy. Therefore, topoisomerase IIα has been considered as more attractive target than topoisomerase IIβ for the development of chemotherapeutic agents. In the previous work, we reported compounds I and II as novel topoisomerase IIα catalytic inhibitors targeting for ATP binding site of human topoisomerase IIα ATP-binding domain. As a continuous work, we have designed and synthesized 43 compounds of C1-O-alkyl and arylalkyl substitiuted compounds with or without methoxy group on ring A. In the topoisomerase IIα inhibitory test, among the tested C1-O-4-chlorophenethyl substituted compounds 37 and 47 were more active than others, and compound 37 showed strongest topoisomerase IIα inhibitory activity with 94.4% and 23.0% inhibition, respectively, at 100 and 20?μM. Compounds 37 and 47 have also showed much enhanced cytotoxic activity against T47D cells; IC50(μM): 0.63?±?0.01 and 0.19?±?0.02, respectively, which are stronger than reference drugs. Band depletion assay and cleavage complex assay results showed compounds 37 and 47 were potential topoisomerase IIα catalytic inhibitor with low DNA damage.

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.

Efficient total synthesis and biological activities of 6-deoxyisojacareubin

6-Deoxyisojacareubin was directly synthesized in a six-step route with an overall yield of about 20%. In this route, the excellent site selectivity of this Claisen rearrangement-cyclization reaction cascade was achieved by inserting a bulky p-tosyl group

NOVEL ANTICANCER-AIDING COMPOUND, METHOD FOR PREPARING THE SAME, ANTICANCER-AIDING COMPOSITION CONTAINING THE SAME AND METHOD FOR REDUCING ANTICANCER DRUG RESISTANCE USING THE SAME

The present invention provides a novel xanthone derivative compound or a pharmaceutically acceptable salt thereof. The compound is useful as a chemosensitizer that reduces anticancer drug resistance.

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

Synthesis of new xanthone analogues and their biological activity test-Cytotoxicity, topoisomerase II inhibition, and DNA cross-linking study

In this report, we prepared some 3-(2′,3′-epoxypropoxy)xanthones and their epoxide ring opened halohydrin analogues, and evaluated their cytotoxicity and topoisomerase II inhibition activity using doxorubicin and etoposide as references, respectively. Another xanthone compound 9, 1,3-di(2′,3′-epoxypropoxy)xanthone, was also synthesized and its DNA cross-linking property including other two biological activities investigated. The biological test results showed compound 9 possessed excellent cytotoxic and topoisomerase II inhibitory activity than other compounds tested. It also exhibited significant DNA cross-linking activities.

Total synthesis of psorospermin

The xanthone natural product psorospermin was synthesized in 13 steps with an overall yield of 1.7%. This compound shows potent antineoplastic activity in a variety of cancer cell lines.