3343-80-4

Usage

Uses

Used in Pharmaceutical Industry:
2-Ethylbenzofuran-3-yl p-methoxyphenyl ketone is used as a precursor for the synthesis of 2-ethylbenzofuran derivatives, which are potential human uric acid transporter 1 (hURAT1) inhibitors. These derivatives have the potential to be developed into treatments for conditions such as hyperuricemia and gout, as they can help regulate uric acid levels in the body by inhibiting the reabsorption of uric acid in the kidneys.

InChI:InChI=1/C18H16O3/c1-3-15-17(14-6-4-5-7-16(14)21-15)18(19)12-8-10-13(20-2)11-9-12/h4-11H,3H2,1-2H3

Upstream product

• 3131-63-3 2-ethylbenzofuran 
• 100-07-2 4-methoxy-benzoyl chloride 
• 1646-26-0 1-(benzo[b]furan-2-yl)ethanone 
• 100-73-2 acrolein dimer 
• 54103-36-5 1-(4-methoxyphenyl)-1,3-pentanedione 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 100-52-7 benzaldehyde 
• 90-02-8 salicylaldehyde 

Downstream Products

• 68-90-6 benziodarone 
• 51073-13-3 benzbromarone methyl ether 
• 3562-84-3 benzbromarone 
• 27432-39-9 1-(2-methoxyphenyl)butan-2-one 
• 65200-70-6 2-(2-methoxyphenyl)-1-(4-methoxyphenyl)ethan-1-one 
• 1477-19-6 benzarone 

Relevant academic research and scientific papers

Preparation method of benzbromarone

The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of benzbromarone. According to the method disclosed by the invention, polystyrene-loaded aluminum trichloride is used as a catalyst to carry out Friedel-Crafts acylation reaction, so that the catalytic effect is good, and the catalyst can be recycled, in the demethylation reaction process, aluminum trichloride is adopted to replace common pyridine hydrochloride, so that the reaction temperature can be reduced, and the yield can be increased, in the bromination reaction, sodium sulfide and hydrogen peroxide are adopted to replace bromine, so that the technical problems of strong corrosivity of bromine, great harm to human bodies and environmental pollution are solved, and meanwhile, the yield can be further improved.

Synthesis method of benzbromarone key intermediate

The invention relates to the technical field of biological medicines, in particular to a synthesis method of a benzbromarone key intermediate, which comprises the following steps: carrying out Friedel-Crafts acylation reaction on 2-ethyl benzofuran and p-methoxybenzoyl chloride under the catalysis of aluminum trichloride by taking methylbenzene as a solvent to generate 2-ethyl-3-p-methoxybenzoyl-benzofuran; and carrying out a demethylation reaction on 2-ethyl-3-p-methoxybenzoyl-benzofuran and aluminum trichloride by taking toluene as a solvent to obtain the key intermediate 2-ethyl-3-p-hydroxybenzoyl-benzofuran of benzbromarone. The synthesis method of the benzbromarone key intermediate, provided by the invention, is mild in reaction condition, the obtained product is relatively high in purity and yield, and the synthesis method has a good industrial production prospect.

Lewis Acid-Catalyzed Synthesis of Benzofurans and 4,5,6,7-Tetrahydrobenzofurans from Acrolein Dimer and 1,3-Dicarbonyl Compounds

2,3-Disubstituted benzofurans were synthesized from acrolein dimer and 1,3-dicarbonyl compounds by using N-bromosuccinimide as an oxidizing agent. The method was used to synthesize two commercial drug molecules, benzbromarone and amiodarone. The proposed mechanism of the reaction involves a N-bromosuccinimide (NBS)-assisted autotandem catalysis with Lewis acid catalyst. To proof the proposed mechanism, an intermediate was isolated successfully, which can be converted to 4,5,6,7-tetrahydrobenzofurans.

Preparation method of 2-ethyl-3-(4-hydroxylbenzoyl) benzofuran

The invention discloses a preparation method of 2-ethyl-3-(4-hydroxylbenzoyl) benzofuran. According to the preparation method, at first, 1-(4-methoxyphenyl)-1,3-pentanedione and acrolein dimer are taken as raw materials to carry out reactions in the presence of an acid catalyst and a halogenation reagent to prepare 2-ethyl-3-(4-methoxyphenyl) benzofuran; then 2-ethyl-3-(4-methoxyphenyl) benzofuranis processed in an organic solvent containing an acid catalyst, and after de-methylation reactions, 2-ethyl-3-(4-hydroxylbenzoyl) benzofuran is obtained. The whole process of key preparation technologies and parameters of each reaction step are optimized; and compared with a conventional synthesis method, the provided preparation method has the advantages of good economy, high selectivity, littleenvironmental pollution, and large industrial application value.

Compound for treatment or prevention of hyperuricemia or gout

The invention discloses a compound for treatment or prevention of hyperuricemia or gout. The compound is the compound shown as formula (I) or formula (II) or pharmaceutical acceptable salts thereof. The compound or its pharmaceutical acceptable salts can be applied to urate excretion promotion so as to treat or prevent hyperuricemia or gout. (formula (1), formula (II)).

DEVELOPING POTENT URATE TRANSPORTER INHIBITORS: COMPOUNDS DESIGNED FOR THEIR URICOSURIC ACTION

A compound represented by the general Formula (I): a pharmaceutically acceptable salt or ester thereof, a solvate thereof, a chelate thereof, a non-covalent complex thereof, a pro-drug thereof, a deuterated radio-labeled analog thereof, and mixtures of any of the foregoing, wherein: A - K are individually selected from carbon or nitrogen; X = -O, -NR1,or -S; R1-11 are individually selected from the group consisting of-H, C1-C6 alkyl, C6-C aryl, substituted C6-C14 aryl, C1-C14-alkoxy, halogen, hydroxyl, carboxy, cyano, C1-C6-alkanoyloxy, C1-C6-alkylthio, C1-C6-alkylsulfonyl, trifluoromethyl, hydroxy, C2-C6-alkoxycarbonyl, C2-C6-alkanoylamino, -O-R12, S-R12,-SO2-Ri2, -NHSO2R12 and -NHCO2R12, wherein R12 is phenyl, naphthyl, or phenyl or naphthly substituted with one to three groups selected from C1-C6-alkyl, C6-C10 aryl,C1-C6-alkoxy and halogen, and C4-C20 hydroxyheteroaryl wherein the heteroatoms are selected from the group consisting of sulfur, nitrogen, and oxygen.

Human uric acid transporter 1 (hURAT1): An inhibitor structure-activity relationship (SAR) study

The current study describes the chemical synthesis of a series of (2-ethylbenzofuran-3-yl)(substituted-phenyl)methanone compounds and their subsequent in vitro testing via oocytes expressing hURAT1. The experimental data support the notion that a potent hURAT1 inhibitor requires an anion (i.e., a formal negative charge) to interact with the positively charged hURAT1 binding pocket. An anion appears to be a primary requirement in order to be a hURAT1 substrate (i.e., urate) or inhibitor. We discuss the inhibitor structure-activity relationship and how electronically donating or withdrawing groups attached to the B-ring can decrease or increase inhibitory potency, respectively. Copyright Taylor and Francis Group, LLC.

Developing potent human uric acid transporter 1 (hURAT1) inhibitors

The kidneys are a vital organ in the human body. They serve several purposes including homeostatic functions such as regulating extracellular fluid volume and maintaining acid-base and electrolyte balance and are essential regarding the excretion of metabolic waste. Furthermore, the kidneys play an important role in uric acid secretion/reabsorption. Abnormalities associated with kidney transporters have been associated with various diseases, such as gout. The current study utilized Xenopus oocytes expressing human uric acid transporter 1 (hURAT1; SLC22A12) as an in vitro method to investigate novel compounds and their ability to inhibit 14C-uric acid uptake via hURAT1. We have prepared and tested a series of 2-ethyl-benzofuran compounds and probed the hURAT1 in vitro inhibitor structure-activity relationship. As compared to dimethoxy analogues, monophenols formed on the C ring showed the best in vitro inhibitory potential. Compounds with submicromolar (i.e., IC 50 1000 nM) inhibitors were prepared by brominating the corresponding phenols to produce compounds with potent uricosuric activity.

Synthesis of 2,3-disubstituted benzofurans on solid-support

A library of 2,3-disubstituted benzofuran scaffold was developed by using intramolecular Wittig olefination and Friedel-Crafts acylation.

Preparation of 2-alkyl-3-(4-hydroxybenzoyl)benzofuran

The invention relates to new molecular complexes of general formula: STR1 in which R represents a straight- or branched-chain alkyl radical having from 1 to 4 carbon atoms and R1 represents one of the radicals: STR2 These molecular complexes are especially useful for the preparation of 2-alkyl-3-(4-hydroxybenzoyl)benzofurans.