83790-87-8

Usage

Uses

Used in Pharmaceutical Synthesis:
(2-butylbenzofuran-3-yl) (4-methoxyphenyl) ketone is used as a key intermediate in the synthesis of pharmaceuticals for its unique molecular configuration that can be further modified to create new drug candidates.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (2-butylbenzofuran-3-yl) (4-methoxyphenyl) ketone is utilized as a building block for the development of novel compounds with potential therapeutic properties, leveraging its versatile chemical structure.
Used in Drug Discovery:
(2-butylbenzofuran-3-yl) (4-methoxyphenyl) ketone serves as a valuable component in drug discovery processes, where its specific structural features can be exploited to design and optimize new molecules with desired biological activities.
Used in Organic Chemistry Research:
(2-butylbenzofuran-3-yl) (4-methoxyphenyl) ketone is also used in organic chemistry research to explore new synthetic pathways, reaction mechanisms, and the development of innovative chemical methodologies, given its complex structure and reactivity.
Used in Chemical Industry:
In the chemical industry, (2-butylbenzofuran-3-yl) (4-methoxyphenyl) ketone may be employed as a specialty chemical for the production of various organic compounds, taking advantage of its unique properties to create new materials or improve existing ones.

InChI:InChI=1/C20H20O3/c1-3-4-8-18-19(16-7-5-6-9-17(16)23-18)20(21)14-10-12-15(22-2)13-11-14/h5-7,9-13H,3-4,8H2,1-2H3

Upstream product

• 4265-27-4 2-n-butylbenzo[b]furan 
• 100-07-2 4-methoxy-benzoyl chloride 
• 90-02-8 salicylaldehyde 
• 5445-19-2 methyl 2-bromohexanoate 
• 138320-26-0 methyl 2-(2-formylphenoxy)hexanoate 
• 138320-27-1 2-(2-formyl-phenoxy)-hexanoic acid 
• 100-09-4 4-methoxybenzoic acid 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 624-24-8 methyl valerate 
• 693-02-7 hex-1-yne 
• 533-58-4 2-Iodophenol 
• 100-73-2 acrolein dimer 
• 1137261-90-5 1-(4-methoxyphenyl)-1,3-heptanedione 
• 75-44-5 phosgene 

Downstream Products

• 52490-15-0 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran 
• 1951-26-4 2-n-butyl-3-(3',5'-diiodo-4'-hydroxybenzoyl)benzofuran 
• 1951-25-3 Amiodarone 
• 19774-82-4 amiodarone hydrochloride 

Relevant academic research and scientific papers

Preparation method of amiodarone hydrochloride key intermediate

The invention discloses a preparation method of an amiodarone hydrochloride key intermediate. The method comprises the following steps: reacting benzofuranone with p-methoxybenzoyl chloride and valeryl chloride, and heating and reacting the product under an acidic condition to obtain the amiodarone hydrochloride key intermediate. According to the method, the key intermediate of amiodarone hydrochloride is prepared through a two-step simple reaction, the reaction condition is mild, byproducts are few, and aftertreatment is easy; due to the fact that aluminum trichloride is not used, no solid waste is generated; and the method has the advantages of simple route operation, high yield and lower cost than the existing route, and is very suitable for industrial production.

Discovery of dronedarone and its analogues as NLRP3 inflammasome inhibitors with potent anti-inflammation activity

Inhibiting NLRP3 inflammasome activation is a prospective therapeutic strategy for uncontrolled inflammatory diseases. It is the first time that dronedarone, a multiply ion channel blocker, was identified as a NLRP3-inflammasome inhibitor with an IC50 value of 6.84 μM against IL-1β release. A series of novel 5-amide benzofuran derivatives were designed and synthesized as NLRP3-inflammasome inhibitors. Compound 8c showed slightly increased activity (IC50 = 3.85 μM) against IL-1β release. Notably, treatment with 8c could significantly inhibit NLRP3-mediated IL-1β release and ameliorate peritoneal inflammation in a mouse model of sepsis. Collectively, 8c is a promising lead compound for further chemical development as a NLRP3 inhibitor with anti-inflammation effects.

Benzofuran compound and application thereof

The invention provides a benzofuran compound as shown in a formula (I) or pharmaceutically acceptable salt thereof, and application thereof. The compound can selectively inhibit activation of NLRP3 inflammasomes and inhibit maturation and secretion of inflammation activation signal molecules Caspase-1 and P20 and inflammatory cytokines IL-1beta, has a good prevention and treatment effect on NLRP3 inflammasome related diseases, and particularly has a remarkable prevention and treatment effect on peritonitis and gouty arthritis. Therefore, the compound can be used for preparing drugs for treating NLRP3 inflammasome-related diseases, such as anti-inflammatory drugs or auxiliary anti-inflammatory drugs.

Preparation method of amiodarone hydrochloride

The invention relates to a preparation method of amiodarone hydrochloride. According to the preparation method, synthesis of intermediate 2-butylbenzofuran is realized under effect of a catalyst, a cocatalyst, and an acid binding agent, through Sonogashira coupling cyclization reaction of 2-iodo phenol and 1-acetylene in an organic solvent at a 2-iodo phenol to 1-acetylene molar ratio of 1:09-1.3,wherein reaction temperature ranges from 30 to 60 DEG C, and reaction time ranges from 12 to 38h. Compared with the prior art, the advantages are that: operation is simplified; operation convenienceand product stability are improved; controlling of the ratio of the catalyst to the materials is capable of increasing the purities and yields of intermediates; no column chromatography purifying is needed; cost is reduced; production efficiency is increased at the same time; and convenience is provided for industrial large scale production.

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 amiodarone hydrochloride intermittent

The invention belongs to the field of medicine synthesis, and relates to a preparation method of an amiodarone hydrochloride intermittent. The method is characterized by including the following stepsthat 1, under an alkaline condition, in the presence of a phase transfer catalyst, a compound 1 and a compound 2 are subjected to nucleophilic substitution reaction to obtain a compound 3; 2, under analkaline condition, the compound 3 is hydrolyzed to generate a compound 4; 3, the compound 4 is subjected to intramolecular aldol condensation, decarboxylation and dehydration to obtain a compound 5;4, a compound 6 and thionyl chloride are subjected to heating reaction to obtain a compound 7; 5, under the presence of lewis acid, the compound 5 and the compound 7 are subjected to friede-crafts acylation reaction to obtain a compound 8; 6, under the presence of lewis acid, the compound 8 is subjected to demethylation to generate a compound 9, namely the amiodarone hydrochloride intermittent 2-butyl-3-(4-hydroxybenzoyl)benzofuran. The preparation method of the amiodarone hydrochloride intermittent has the advantages of being short in reaction time, high in product purity and high in yield,and the amiodarone hydrochloride intermittent is suitable for large-scale industrial production.

A 2 - butyl - 3 - (4 - hydroxy benzoyl) benzofuran preparation method (by machine translation)

The invention discloses a 2 - butyl - 3 - (4 - hydroxy benzoyl) benzofuran of the preparation method, the preparation method comprises the following steps: (1) the 1 - (4 - methoxyphenyl) - 1, 3 - heptyl diketone, acrolein dimer, halogenated reagent and acid catalyst in organic solvent for 25 - 100 °C stirring reaction for 1 - 8 hours, to obtain the 2 - butyl - 3 - (4 - anisoyl) benzofuran; (2) the 2 - butyl - 3 - (4 - anisoyl) benzofuran is dispersed in the organic solvent containing the acid catalyst used in the 0 - 100 °C stirring for 1 - 8 hours, to obtain the 2 - butyl - 3 - (4 - hydroxy benzoyl) benzofuran. The invention through the key process for the preparation of the overall process, and each reaction step of optimizing the parameter condition and the like, with the traditional 2 - butyl - 3 - (4 - hydroxy benzoyl) benzofuran existing synthesis method, with a route good economic performance, high reaction selectivity, industrial application value is large and the like. (by machine translation)

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.

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.

Process for the preparation of 3-benzoyl benzofuran derivatives

The invention relates to a process for the preparation of 3-benzoyl benzofuran derivatives of general formula: STR1 wherein a benzofuran derivative of general formula: STR2 is reacted in situ in the presence of aluminium chloride successively with phosgene or oxalyl chloride, and then with a phenolic derivative of general formula: STR3 to produce a complex which is hydrolysed to form the desired compound of 3-benzoyl benzofuran.