1915-98-6

Usage

InChI:InChI=1/C13H8O3/c14-8-5-6-12-10(7-8)13(15)9-3-1-2-4-11(9)16-12/h1-7,14H

Upstream product

• 108239-96-9 1-acetyl-2-hydroxy-xanthen-9-one 
• 89450-90-8 2-hydroxy-9-oxo-xanthene-1-carboxylic acid 
• 1214-20-6 2-methoxy-9H-xanthen-9-one 
• 1916-04-7 2-(4-methoxyphenoxy)benzoic acid 
• 150-76-5 4-methoxy-phenol 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 101597-66-4 2-(3-acetyl-4-hydroxy-phenoxy)-benzoic acid ethyl ester 
• 75-09-2 dichloromethane 
• 38731-89-4 2-methoxy-9H-xanthene 
• 61234-53-5 4a-methoxy-2H-xanthene-2,9(4aH)-dione 
• 1122-95-8 sodium 4-methoxyphenolate 
• 17264-74-3 sodium 2-chlorobenzoate 
• 123-31-9 hydroquinone 
• 118-61-6 2-hydroxy-benzoic acid ethyl ester 

Downstream Products

• 103573-60-0 2-Ethoxyxanthone 
• 274902-92-0 2-[2-(4-toluenesulfonyloxy)eth-1-yl]xanthone 
• 1445772-45-1 9-oxo-9H-xanthen-2-yl trifluoromethanesulfonate 
• 80553-15-7 O-phenyl O-(xanthen-9-one-2-yl) S-propyl phosphorothiolate 
• 111444-79-2 1-[(2,4-dinitro-phenylhydrazono)-methyl]-2-hydroxy-xanthen-9-one 
• 103036-11-9 1,2-bis-benzyloxy-xanthen-9-one 
• 102555-55-5 2-benzyloxy-1-hydroxy-xanthen-9-one 
• 152810-94-1 N-(2-Ethoxy-9H-xanthen-9-yl) benzyl carbamate 
• 164934-46-7 2-{2-[(3-hydroxy-benzyl)-methyl-amino]-ethoxy}-xanthen-9-one 
• 164934-41-2 2-{2-[(3-methoxy-benzyl)-methyl-amino]-ethoxy}-xanthen-9-one 
• 164934-31-0 2-[2-(benzyl-methyl-amino)-ethoxy]-xanthen-9-one 

Relevant academic research and scientific papers

Synthesis and solid-phase application of a 9-xanthenyl handle

The acid-labile 5-[(9-aminoxanthen-2-yl)oxy]valeric acid was prepared in a six-step route. The usefulness of the resulting handle was investigated with solid-phase peptide synthesis of cholecystokinin-8 sulfate and the phosphorylated fragment of the ζ-sub

The involvement of xanthone and (E)-cinnamoyl chromophores for the design and synthesis of novel sunscreening agents

Excessive UV exposure contributes to several pathological conditions like skin burns, er-ythema, premature skin aging, photodermatoses, immunosuppression, and skin carcinogenesis. Effective protection from UV radiation may be achieved with the use of sunscreens containing UV filters. Currently used UV filters are characterized by some limitations including systemic absorp-tion, endocrine disruption, skin allergy induction, and cytotoxicity. In the research centers all over the world new molecules are developed to improve the safety, photostability, solubility, and absorption profile of new derivatives. In our study, we designed and synthesized seventeen novel molecules by combining in the structures two chromophores: xanthone and (E)-cinnamoyl moiety. The ultraviolet spectroscopic properties of the tested compounds were confirmed in chloroform solutions. They acted as UVB or UVA/UVB absorbers. The most promising compound 9 (6-meth-oxy-9-oxo-9H-xanthen-2-yl)methyl (E)-3-(2,4-dimethoxyphenyl)acrylate) absorbed UV radiation in the range 290–369 nm. Its photoprotective activity and functional photostability were further evaluated after wet milling and incorporation in the cream base. This tested formulation with compound 9 possessed very beneficial UV protection parameters (SPFin vitro of 19.69 ± 0.46 and UVA PF of 12.64 ± 0.32) which were similar as broad-spectrum UV filter tris-biphenyl triazine. Additionally, compound 9 was characterized by high values of critical wavelength (381 nm) and UVA/UVB ratio (0.830) thus it was a good candidate for broad-spectrum UV filter and it might protect skin against UVA-induced photoaging. Compound 9 were also shown to be photostable, non-cytotoxic at con-centrations up to 50 μM when tested on five cell lines, and non-mutagenic in Ames test. It also possessed no estrogenic activity, according to the results of MCF-7 breast cancer model. Addition-ally, its favorable lipophilicity (miLogP = 5.62) does not predispose it to penetrate across the skin after topical application.

Rational design of new multitarget histamine H3 receptor ligands as potential candidates for treatment of Alzheimer's disease

Design and development of multitarget-directed ligands (MTDLs) has become a very important approach in the search of new therapies for Alzheimer's disease (AD). In our present research, a number of xanthone derivatives were first designed using a pharmaco

REAGENTS AND PROCESS FOR DIRECT C-H FUNCTIONALIZATION

Thianthrene derivative of the Formula (I): wherein R1 to R8 may be the same or different and are selected from hydrogen, Cl, F, a partially or fully fluorinated C1 to C6 alkyl group, and wherein n is 0 or 1, with the proviso that at least one of R1 to R8 is not hydrogen and process for C-H functionalization of aromatic compounds using this compound.

Site-Selective C?H Oxygenation via Aryl Sulfonium Salts

Herein, we report a two-step process forming arene C?O bonds in excellent site-selectivity at a late-stage. The C?O bond formation is achieved by selective introduction of a thianthrenium group, which is then converted into C?O bonds using photoredox chemistry. Electron-rich, -poor and -neutral arenes as well as complex drug-like small molecules are successfully transformed into both phenols and various ethers. The sequence differs conceptually from all previous arene oxygenation reactions in that oxygen functionality can be incorporated into complex small molecules at a late stage site-selectively, which has not been shown via aryl halides.

Ceric Ammonium Sulfate (CAS) Mediated Oxidations of Benzophenones Possessing a Phenolic Substituent for the Synthesis of Xanthones and Related Products

Work previously published by our group described novel methodology for the synthesis of xanthones and related products from phenolic benzophenones in a reaction mediated by ceric ammonium sulfate (CAS). In this paper we further explore this novel reaction by subjecting an additional set of phenolic benzophenones to CAS to afford a range of compounds, including xanthones, 9H-xanthen-2,9(4aH)-diones, 3H-spiro[benzofuran-2,1′-cyclohexa[2,5]diene]-3,4′-diones, and biaryl compounds. A comparison of these reactions with the more commonly used oxidant ceric ammonium nitrate (CAN) was also conducted. Based on these results, greater insight into the reaction mechanism has been gained. In addition, the conversion of the synthesized xanthen-2,9(4aH)-diones to xanthones by treatment with sodium dithionite is described.

Design, synthesis, and anticonvulsant activity of some derivatives of xanthone with aminoalkanol moieties

A series of new xanthone derivatives have been synthesized and evaluated for their anticonvulsant properties in the maximal electroshock, subcutaneous metrazole tests and for neurotoxicity in the rotarod in mice, i.p. and rats, p.o. Compound 9: R,S-2-{2-[(1-hydroxybutan-2-yl]amino)ethoxy}-9H-xanthen-9-one and compound 12: R,S-2-{3-[(1-hydroxybutan-2-yl)amino]propoxy}-9H-xanthen-9-one exerted activity in rats, p.o. 2 and 4?h after administration, respectively. Therefore, metabolic stability of the compounds was evaluated with use of rat microsomes, resulting in half-life t1/2 136 and 108?min, respectively, indicating that either the metabolites are very active or the parent compounds exert ADME properties other than metabolism which influence the late onset of activity.

Synthesis and fluorescence of xanthone amino acids

Fmoc- and Boc-protected α-amino acids bearing xanthone as side chain are easily accessible by palladium-catalyzed cross-coupling of a xanthone triflate with appropriate amino acid residues. The xanthone triflate was obtained in three steps taking advantag

A comprehensive study on infrared spectra of 2-hydroxyxanthone

A study on the IR spectra of 2-hydroxyxanthone that was both experimental and theoretical was carried out in this work. The optimized structure and related spectral parameters were obtained by using the Becke-3-Lee-Yang-Parr (B3LYP) method with the 6-31G* and 6-311G** basis sets. The corresponding geometrical parameters were compared with each other. Detailed assignments of the vibration frequencies were performed. The agreement between the scaled theoretical frequencies and the observed frequencies was found to be quite good. Also, the calculation accuracies of the two basis sets are close. Copyright Taylor & Francis Group, LLC.

Rhodium-catalyzed xanthone formation from 2-aryloxybenzaldehydes via cross-dehydrogenative coupling (CDC)

A concise and straightforward strategy to construct a xanthone skeleton via an intramolecular cross-dehydrogenative coupling (CDC) of 2- aryloxybenzaldehydes has been developed. The reaction proceeded smoothly without any need of preactivation of the aldehyde group. It can tolerate various functional groups and provides an applicable protocol to construct a wide range of xanthone derivatives.