503300-08-1

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 768-60-5 4-methoxyphenylacetylen 
• 610-71-9 2,5-dibromobenzoic acid 
• 136105-40-3 1,4-dibromo-2-(bromomethyl)benzene 
• 123-11-5 4-methoxy-benzaldehyde 
• 2316-64-5 5-bromo-2-hydroxybenzyl alcohol 
• 1761-61-1 5-bromosalicyclaldehyde 
• 100-07-2 4-methoxy-benzoyl chloride 
• 33397-21-6 tris(4-methoxyphenyl)bismuth 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 540520-73-8 2-(4-bromophenoxy)-1-(4-methoxyphenyl)ethan-1-one 
• 1060684-44-7 4-bromo-O-triisopropylsilyl-2-iodophenol 
• 696-62-8 para-iodoanisole 
• 78-27-3 1-Ethynylcyclohexan-1-ol 

Downstream Products

• 90178-96-4 5-Brom-2-(4-hydroxyphenyl)-1-benzofuran 

Relevant academic research and scientific papers

Strategy for Overcoming Full Reversibility of Intermolecular Radical Addition to Aldehydes: Tandem C-H and C-O Bonds Cleaving Cyclization of (Phenoxymethyl)arenes with Carbonyls to Benzofurans

An intermolecular addition of carbon radicals enabled by a cascade radical coupling strategy is developed. It includes an intermolecular alkyl radical addition to a carbonyl group followed by an intramolecular alkoxy radical addition to haloarenes and produces substituted benzofurans in high yields. The radical nature of this reaction is explored by radical trapping experiments and EPR analysis. The mechanism is investigated by KIE experiments and control experiments. This method could provide rapid and practical access to the key intermediate of TAM-16, a safe and potent antibacterial agent for treating tuberculosis, and, therefore, is of great importance for organic synthesis and the pharmaceutical industry.

2-Phenylbenzofuran derivatives as butyrylcholinesterase inhibitors: Synthesis, biological activity and molecular modeling

A series of 2-phenylbenzofurans compounds was designed, synthesized and evaluated as cholinesterase inhibitors. The biological assay experiments showed that most of the compounds displayed a clearly selective inhibition for butyrylcholinesterase (BChE), while a weak or no effect towards acetylcholinesterase (AChE) was detected. Among these benzofuran derivatives, compound 16 exhibited the highest BChE inhibition with an IC50 value of 30.3 μM. This compound was found to be a mixed-type inhibitor as determined by kinetic analysis. Moreover, molecular dynamics simulations revealed that compound 16 binds to both the catalytic anionic site (CAS) and peripheral anionic site (PAS) of BChE and it displayed the best interaction energy value, in agreement with our experimental data.

MAO Inhibitory Activity of 2-Arylbenzofurans versus 3-Arylcoumarins: Synthesis, invitro Study, and Docking Calculations

Monoamine oxidase (MAO) is an important drug target for the treatment of neurological disorders. Several 3-arylcoumarin derivatives were previously described as interesting selective MAO-B inhibitors. Preserving the trans-stilbene structure, a series of 2-arylbenzofuran and corresponding 3-arylcoumarin derivatives were synthesized and evaluated as inhibitors of both MAO isoforms, MAO-A and MAO-B. In general, both types of derivatives were found to be selective MAO-B inhibitors, with IC50 values in the nano- to micromolar range. 5-Nitro-2-(4-methoxyphenyl)benzofuran (8) is the most active compound of the benzofuran series, presenting MAO-B selectivity and reversible inhibition (IC50=140nM). 3-(4′-Methoxyphenyl)-6-nitrocoumarin (15), with the same substitution pattern as that of compound 8, was found to be the most active MAO-B inhibitor of the coumarin series (IC50=3nM). However, 3-phenylcoumarin 14 showed activity in the same range (IC50=6nM), is reversible, and also severalfold more selective than compound 15. Docking experiments for the most active compounds into the MAO-B and MAO-A binding pockets highlighted different interactions between the derivative classes (2-arylbenzofurans and 3-arylcoumarins), and provided new information about the enzyme-inhibitor interaction and the potential therapeutic application of these scaffolds.

Palladium-catalyzed cross-couplings of functionalized 2-bromobenzofurans for atom-economic synthesis of 2-arylbenzofurans using triarylbismuth reagents

The palladium catalyzed, atom-economic synthesis of various functionalized 2-arylbenzofurans was achieved through cross-coupling reaction of 2-bromobenzofurans with triarylbismuth reagents. The palladium catalytic protocol is very efficient to furnish various cross-coupled functionalized 2-arylbenzofurnas in high yields using triarylbismuth reagents with three aryl couplings as multi-coupling organometallic nucleophiles in one-pot operation. All the coupling reactions were completed in 1 h short reaction time involving three couplings from triarylbismuths under heating condition.

GLUCOPYRANOSIDE DERIVATIVES

Novel compounds of the formula (I), in which X has the meaning indicated in Patent Claim 1, are suitable as antidiabetics.

A convenient two-step synthesis of 2-arylbenzofurans

A novel and convenient two-step synthesis of 2-arylbenzofurans is described which proceeds via a selective cross-pinacol-type coupling between a salicylaldehyde and an aromatic aldehyde, followed by an acid-promoted cyclization. One advantage of this method is that separation of the three possible pinacol products that can form during the cross-coupling is not necessary. This method is also applied to the synthesis of the 2-arylbenzofuran-containing natural product, homoegonol.

PHARMACEUTICAL COMPOSITIONS AND METHODS OF PREVENTING, TREATING, OR INHIBITING INFLAMMATORY DISEASES, DISORDERS, OR CONDITIONS OF THE SKIN, AND DISEASES, DISORDERS, OR CONDITIONS ASSOCIATED WITH COLLAGEN DEPLETION

The present invention provides compositions and methods for preventing, treating, or inhibiting inflammatory diseases, disorders, or conditions of the skin, and diseases, disorders, or conditions associated with collagen depletion using one or more estrogenic agents.

Development of a one-pot sequential Sonogashira coupling for the synthesis of benzofurans

An efficient one-pot protocol was developed for the construction of the benzofuran system from aryl halides and protected iodophenols using carbinol-based acetylene sources. The sequence includes alternating palladium-catalyzed Sonogashira couplings and deprotection steps concluded by a ring closure. The developed one-pot procedure was compared with the stepwise approach and its efficiency was also demonstrated by the total synthesis of vignafuran, a benzofuran natural product.

Substituted 2-phenyl benzofurans as estrogenic agents

This invention provides estrogen receptor modulators of formula I, having the structure wherein R, R′, A, A′, X, Y, and Y are as defined in the specification, or a pharmaceutically acceptable salt thereof.

2,3-Disubstituted 2,3,5-trisubstituted benzofurans by regioselective Pd-catalyzed cross-coupling reactions; a short synthesis of eupomatenoid-15

2,3-Dibromobenzofuran (1) 2,3,5-tribromobenzofuran (2) undergo regioselective Sonogashira- Negishi-type cross-coupling reactions at the 2-position. Subsequent substitution reactions at C-3 are possible for the cross-coupling products obtained from compoun