6155-37-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-methyl ester is used as an intermediate in the synthesis of Rhein 8-Glucoside (R318520), a compound with demonstrated cytotoxic and DNA-damaging properties towards tumor and normal human cells. Its ability to inhibit PTP1B (Human Protein Tyrosine Kinase 1B) in vitro makes it a promising candidate for the development of new therapeutic agents in the fight against cancer.
Used in Antioxidant Applications:
As an analog of Rhein (318500), which is found in the free state and as glucoside in Rheum spp, Polygonaceae (rhubarb), and in Senna leaves, 2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-methyl ester has the potential to be utilized as an antioxidant resource. Antioxidants are essential in various industries, including pharmaceuticals, cosmetics, and the food industry, to protect against oxidative stress and maintain the stability and shelf life of products.
Used in Research and Development:
Due to its unique chemical structure, 2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-methyl ester can be employed in research and development for the synthesis of novel compounds with potential applications in various fields, such as pharmaceuticals, materials science, and chemical engineering. Its reactivity and structural features make it a valuable starting material for the development of new molecules with specific properties and functions.

Upstream product

• 478-43-3 1,8-dihydroxy-3-carboxy-anthraquinone 
• 74-88-4 methyl iodide 
• 61350-19-4 4,5,7-triacetoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid 
• 6030-60-0 1,6,8-triacetoxy-3-methyl-9,10-anthraquinone 
• 518-82-1 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone 
• 80301-52-6 9,10-Dihydroxy-5-methoxy-4-oxo-1,2,3,4-tetrahydro-anthracene-2-carboxylic acid methyl ester 
• 65131-09-1 7-methoxy-3-(phenylsulfonyl)-1(3H)-isobenzofuranone 
• 80301-53-7 4-Hydroxy-5-methoxy-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid methyl ester 
• 67-56-1 methanol 

Downstream Products

• 481-72-1 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione 
• 478-43-3 1,8-dihydroxy-3-carboxy-anthraquinone 

Relevant academic research and scientific papers

Upregulation of p53 through induction of MDM2 degradation: Amino acid prodrugs of anthraquinone analogs

Previously, we reported a class of MDM2-MDM4 dimerization inhibitors that upregulate p53 and showed potent anticancer activity in animal models. However, water solubility hinders their further development. Herein we describe our effort to develop a prodru

A biocatalytic approach towards the preparation of natural deoxyanthraquinones and their impact on cellular viability

Herein, a two-step chemoenzymatic process for the synthesis of medicinally important 3-deoxygenated anthra-9,10-quinones is developed. It involves a regio- and stereoselective reduction of hydroanthraquinones to (R)-configured dihydroanthracenones using an anthrol reductase of T. islandicus, followed by oxidation and dehydration to obtain deoxyanthraquinones in 65-80% yield. Comparison of the cell viability of normal human kidney HEK293 cells between anthraquinones and their deoxy derivatives revealed less toxicity for the latter.

Preparation method of parietic acid-amino acid conjugate

The invention belongs to the technical field of organic compound synthesis, and particularly relates to a preparation method of a parietic acid-amino acid conjugate. The preparation method comprises the following steps of weighing 1 to 2g of methyl methacrylate; putting the methyl methacrylate into a reaction container; then adding 35 to 45ml of DMAP, 0.3 to 0.8g of strong base sodium hydride and1 to 3g of halohydrocarbon at the reaction temperature of 100 to 120 DEG C for the reaction time of 10 to 25min; then, adding 40 to 60 ml of hydrochloric acid solution; performing constant temperaturereaction for 5 to 10min; after the reaction is completed, performing extraction by dichloromethane; adding the extracted products into 35 to 38ml of sodium hydroxide solution; performing reaction atthe temperature of 50 to 60 DEG C for 15 to 30min; performing high-speed stirring; then regulating the pH into a weak acid state; adding 1 to 3g of amino-acid ester; performing room temperature stirring reaction for 5 to 10min; adding 40 to 60ml of hydrochloric acid solutions; performing constant temperature reaction for 5 to 10min; after the reaction is completed, performing extraction for 2 to 4times by dichloromethane; after the solid is separated, performing filtering; performing drying by anhydrous sodium sulfate; obtaining a finished product. The preparation method has the advantages that the dissolution is easy; the bioavailability is high; the process equipment requirement conditions are low; the process steps are simple; the synthesis rate is high, and the like.

ANTHRAQUINONE ANALOGS AND METHODS OF MAKING AND USING THEREOF

Rhein analogues that exhibit anti-proliferative activity, particular against cancer cells, are described herein. In some embodiments, the compounds contain a flat or planar ring system. Such rings system by facilitate non-covalent binding of the compounds to the DNA complex, such as by intercalation. In some embodiment, the compounds contain a flat or planar ring system as described above and one or more substituents which are alkylating moieties, electrophilic groups or Michael acceptors or groups which contain one or more alkylating moieties, electrophilic groups and/or Michael acceptors. The compounds described herein can also contain one more functional groups to improve the solubility of the compounds.

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.