129-43-1

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 55, p. 350, 1990 DOI: 10.1021/jo00288a062

InChI:InChI=1/C14H8O3/c15-11-7-3-6-10-12(11)14(17)9-5-2-1-4-8(9)13(10)16/h1-7,15H

Upstream product

• 110-86-1 pyridine 
• 82-34-8 1-nitroanthraquinone 
• 56-23-5 tetrachloromethane 
• 70063-66-0 1-acetoxy-5-hydroxy-9,10-dioxo-1,4,4a,9,9a,10-hexahydroanthracene 
• 73794-49-7 1-acetoxy-8-hydroxy-9,10-dioxo-1,4,4a,9,9a,10-hexahydroanthracene 
• 85-44-9 phthalic anhydride 
• 108-95-2 phenol 
• 35694-36-1 1c,4t-diacetoxy-buta-1,3-diene 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 15910-11-9 1,4-diacetoxy 1,3-butadiene 
• 632-83-7 1-Bromoanthraquinone 
• 54016-87-4 4-hydroxy-anthrone 
• 6079-73-8 2-hydroxybenzoylbenzoic acid 
• 116-85-8 4-hydroxy-1-aminoanthraquinone 

Downstream Products

• 1629-56-7 1-acetoxy-9,10-anthraquinone 
• 873991-74-3 9,10-diphenyl-9,10-dihydro-anthracene-1,9,10-triol 
• 123412-37-3 1-<<(4-fluorophenyl)sulfonyl>oxy>-9,10-anthraquinone 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 56670-83-8 1-hydroxyanthraquinone-2-sulfonic acid 
• 36287-93-1 sodium 1-hydroxyanthraquinone-2-sulphonate 
• 76187-49-0 sodium 1-hydroxyanthraquinone-4-sulphonate 
• 76187-50-3 disodium 1-hydroxyanthraquinone-2,4-disulphonate 
• 54454-84-1 2-benzyl-1-hydroxy-9,10-anthraquinone 
• 79207-95-7 1-hydroxy-4-butylantraquinone 
• 63768-01-4 1-(butylamino)-4-hydroxyanthracene-9,10-dione 
• 79207-96-8 1-hydroxy-2,4-bis(butylamino)antraquinone 
• 107035-89-2 1-<<(4-methylphenyl)sulfonyl>oxy>-9,10-anthraquinone 
• 82-39-3 1-methoxyanthracene-9,10-dione 

Relevant academic research and scientific papers

Substitution of Quinizarin and 5-Hydroxyquinizarin at C-2

Carbanions derived from ethyl acetoacetate, acetylacetone, and alkyl nitro-compounds add to C-2 of quinizarin and its 5-hydroxy-derivative.

Synthesis of functionalized 1,4-dihydro-9,10-anthraquinones and anthraquinones by ring closing metathesis using Grubbs' catalyst

A general and straightforward synthesis of anthraquinones was developed, in which diallylation of 1,4-naphthoquinones, followed by Ring Closing Metathesis (RCM) of the resulting diallylnaphthoquinones with Grubbs' catalyst and subsequent dehydrogenation using Pd/C afforded the desired anthraquinones with regiocontrol of substituents and in good yields.

Novel Oxidative Transformation: Regiospecific Preparation of Naturally Occurring 1-Hydroxyanthraquinones

A brief reaction sequence for synthesis of the naturally occurring anthraquinones 1-hydroxyanthraquinone (4a), 1-hydroxy-2-methylanthraquinone (4b), pachybasin (4c), chrysophanol (5a), and rhein (5c) has been developed.

Preparation of 3,4-Dihydroanthracen-1(2H)-ones. A Synthetic Approach to Islandicin and Digitopurpone via Difluoro1,O9>boron Chelates

Three 9,10-dihydroxyanthracen-1(2H)-one derivatives (2a-c) have been obtained by the catalytic hydrogenation of quinizarin, 1-hydroxy-5-methoxyanthraquinone, and 1-hydroxy-8-methoxyanthraquinone, respectively; in the last two reactions, monohydroxyanthracen-1(2H)-ones (4a) and (4b) are formed as by-products.The anthracenone derivatives (2a-c) were O-methylated by methyl toluene-p-sulphonate and the selective demethylation of the dimethoxy derivative (2d) to the monomethoxy derivative (2e) was effected by AlCl3.The silyl enolate (5) was unreactive toward C-methylation but the lithium enolate of the anthracenone (2d) reacted with methyl iodide to give a mixture of C-mono (2f) and C-di (6a) alkylated derivatives; in contrast, the boron enolate of (2d) reacted with methyl iodide to give exclusively the C-monomethylated derivative (2f) and this procedure was extended to the synthesis of 5-methoxy (2g) and 8-methoxy (2h) analogues of (2f).Whereas the dimethoxyanthracenone derivative (2d) is brominated (Br2-CHCl3, 0 deg C) in separate reactions to give monobromo (2i) and dibromo (6b) derivatives, the difluoroboron chelate (9a) was converted by photochemical bromination into a product (9g) of benzylic substitution; the analogue (9h) was similarly obtained from the difluoroboron chelate (9b).The boron derivatives (9g) and (9h) were transformed by methanol into hydroxydimethoxyanthracenone derivatives (2l) and (2m), and (9g) was also converted by wet alumina into the dihydroxymethoxyanthracenone (2n).The hydroxydimethoxyanthracenone (2l) and (2m) were transformed by 2,3-dichloro-5,6-dicyanobenzoquinone and selenium dioxide into 1-hydroxy-4-methoxyanthraquinone and 1-hydroxy-4-methoxy-2-methylanthraquinone, respectively.

Copper-catalyzed one-pot relay synthesis of anthraquinone based pyrimidine derivative as a probe for antioxidant and antidiabetic activity

Synthetic compounds have modernized the globe due to its vast applicable fields. Anthraquinones, as well as pyrimidine derivatives, are used as essential pharmacophores in the field of medicine. Maintenance of a green disease-free environment by using these derivatives is being acknowledged in developed as well as developing countries of the world. Considering the use of active catalysts in the synthesis of anthraquinone based derivatives are the era of concern for researchers due to their distinctive properties. Owing to the remarkable activities of anthraquinone and pyrimidine derivative, we synthesize compounds having both functionalities with the utilization of novel synergically active copper catalysts. This study explores the application of synthesized compounds using fast, ecofriendly and cost-effective approaches.1H and 13C NMR, antioxidant, antidiabetic, molecular docking and QSAR studies were used for characterization and evaluation of newly synthesized anthraquinone based pyrimidine derivatives. The result of these techniques shows that our desired compounds were successfully synthesized and have potent applications. Among all synthesized compounds, G2 and G3 showed a remarkable antioxidant activity with IC50 of 15.09 and 21.88 μg/ml respectively. While the compound G2 and G4 showed a strong inhibitory antidiabetic activity with the IC50 value of 24.23 and 28.94 μg/ml respectively. Furthermore, molecular docking results for both of the proteins assist the experimental data and confirms the different interactions between binding domains and substituent moieties. SAR study also relates to the experimental facts by giving us positive results of synthesized compounds. According to the QSAR study, G4 and G2 emerged as the most stable and most reactive compound among other compounds respectively. While MEP shows moderate to good nucleophilic and electrophilic reactivity of all four compounds.

TARGETED BIFUNCTIONAL DEGRADERS

The present invention provides, in one aspect, bifunctional compounds that can be used to promote or enhance degradation of certain circulating proteins. In another aspect, the present invention provides bifunctional compounds that can be used to promote or enhance degradation of certain autoantibodies. In certain embodiments, treatment or management of a disease and/or disorder requires degradation, removal, or reduction in concentration of the circulating protein or the autoantibody in the subject. Thus, in certain embodiments, administration of a compound of the invention to the subject removes or reduces the circulation concentration of the circulating protein or the autoantibody, thus treating, ameliorating, or preventing the disease and/or disorder. In certain embodiments, the circulating protein is TNF.

BIFUNCTIONAL SMALL MOLECULES TO TARGET THE SELECTIVE DEGRADATION OF CIRCULATING PROTEINS

The present invention is directed to bifunctional small molecules which contain a circulating protein binding moiety (CPBM) linked through a linker group to a cellular receptor binding moiety (CRBM) which is a membrane receptor of degrading cell such as a hepatocyte or other degrading cell. In embodiments, the (CRBM) is a moiety which binds to asialoglycoprotein receptor (an asialoglycoprotein receptor binding moiety, or ASGPRBM) of a hepatocyte. In additional embodiments, the (CRBM) is a moiety which binds to a receptor of other cells which can degrade proteins, such as a LRP1, LDLR, FcyRI, FcRN, Transferrin or Macrophage Scavenger receptor. Pharmaceutical compositions based upon these bifunctional small molecules represent an additional aspect of the present invention. These compounds and/or compositions may be used to treat disease states and conditions by removing circulating proteins through degradation in the hepatocytes or macrophages of a patient or subject in need of therapy. Methods of treating disease states and/or conditions in which circulating proteins are associated with the disease state and/or condition are also described herein.

Efficient reductive Claisen rearrangement of prop-2’-enyloxyanthraquinones and 2’-chloroprop-2’-enyloxyanthraquinones with iron powder in ionic liquids

A rapid and selective iron-mediated reductive Claisen rearrangement of various prop-2’-enyloxyanthraquinones and 2’-chloroprop-2’-enyloxyanthraquinones to 1-hydroxy-2-(prop-2’-enyl)anthraquinones and anthrafurandiones is presented. All reactions are carried out in a mixture of ionic liquids, [Bzmim]Cl (1-benzyl-3-methylimidazolium chloride) and [Hmim]BF4 (1-methylimidazolium tetrafluoroborate), in short reaction times (5–35 min). Our study showed that 1-(prop-2’-enyloxy)anthraquinone is more active than 1-(2’-chloroprop-2’-enyloxy)anthraquinone to perform this rearrangement.

Preparation method of 4-hydroxyindole

The invention discloses a preparation method of 4-hydroxyindole, comprising the steps of (1) dissolving 3-methoxyphenylhydrazine hydrochloride in DMF (dimethylformamide), adding concentrated sulfuricacid and a catalyst, mixing well, adding acetaldehyde, allowing reflux reaction at controlled temperature of 60-80 DEG C for 90-120 min, filtering after reaction is over to obtain 4-methoxyindole; (2)dissolving 4-methoxyindole in dichloromethane, adding the obtained solution in a reactor, introducing nitrogen, controlling the temperature to 50-70 DEG C, and introducing HBr into the solution, allowing reflux reaction for 45-90 min, lowering the temperature to room temperature, performing reduced pressure removal of a solvent, and recrystallizing to obtain 4-hydroxyindole. The preparation method according to the application is simple to perform and has mild conditions and few byproducts, the product is high in purity, and the yield of the product is high.

Synthesis method of anthraquinone derivatives and tetracenedione derivatives through benzannulation reaction

The present invention relates to a method for synthesizing anthraquinone derivatives and tetracene dione derivatives through a benzannulation reaction, which presents a novel synthesis method, capable of processing synthesis easily, conveniently, and efficiently under mild conditions by an organic catalyst. The synthesis method uses an L-proline catalyst which is nontoxic, economical and easily available, compared to conventional production methods, thereby providing the anthraquinone derivatives and the tetracene dione derivatives through the one-pot benzannulation reaction of an α, β-unsaturated aldehyde compound, various 1,4-naphthoquinone compounds or 1,4-anthracenedione compounds. Various forms of anthraquinone derivatives or tetracene dione derivatives prepared by the synthesis method can be widely used for synthesis of natural products, dyes, and pharmaceutical products.COPYRIGHT KIPO 2017