50551-57-0

Basic information

• Product Name: ethyl 6-methoxybenzofuran-2-carboxylate
• Synonyms: ethyl 6-methoxybenzofuran-2-carboxylate;2-Benzofurancarboxylic acid, 6-Methoxy-, ethyl ester;ethyl 6-Methoxy-1-benzofuran-2-carboxylate;ETHYL 6-METHOXYBENZOFURAN-2-CARBOXYLATE(WXC06043)
• CAS NO: 50551-57-0
• Molecular Formula: C12H12O4
• Molecular Weight: 220
• Mol File: 50551-57-0.mol

Chemical Properties

• Melting Point: 87 °C
• Boiling Point: 316.2±22.0 °C(Predicted)
• Appearance: /
• Density: 1.192±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: ethyl 6-methoxybenzofuran-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 6-methoxybenzofuran-2-carboxylate(50551-57-0)
• EPA Substance Registry System: ethyl 6-methoxybenzofuran-2-carboxylate(50551-57-0)

Safety Data

• Hazardous Substances Data: 50551-57-0(Hazardous Substances Data)

Upstream product

• 76322-06-0 2-ethoxycarbonylmethoxy-4-methoxybenzaldehyde 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 685-87-0 Diethyl 2-bromomalonate 
• 150-19-6 O-methylresorcine 
• 4504-12-5 ethyl 5-oxo-2-phenyl-2,5-dihydroisoxazole-4-carboxaldehyde 
• 105-36-2 ethyl bromoacetate 
• 105-39-5 chloroacetic acid ethyl ester 

Downstream Products

• 50551-61-6 6-methoxybenzofuran-2-carboxylic acid 
• 41910-91-2 2,3-dihydro-2-carboxy-6-methoxybenzofuran 
• 53860-74-5 6-methoxy-1-benzofuran-2-carbaldehyde 
• 1254572-50-3 C₁₉H₁₈N₂O₂ 
• 1462470-22-9 ((6-methoxybenzofuran-2-yl)methyl)triphenylphosphonium bromide 
• 1089681-42-4 (E)-6-methoxy 2-(4-dimethylaminostyryl)benzofuran 
• 1089681-44-6 (E)-6-hydroxy 2-(4-dimethylaminostyryl)benzofuran 
• 1462469-84-6 (E)-6-(2-(3-oxazolidinyl)ethoxy)-2-(4-dimethylaminostyryl)benzofuran 
• 1462470-44-5 (E)-6-(methoxy)-2-(4,4′-methyl(2-fluoroethyl)aminostyryl)benzofuran 
• 1089682-48-3 (E)-tert-butyl (4-(2-(6-methoxybenzofuran-2-yl)vinyl)phenyl)(methyl)carbamate 
• 1089681-69-5 (E)-4-(2-(6-methoxybenzofuran-2-yl)vinyl)-N-methylaniline 
• 1462470-08-1 (E)-6-(2-(3-oxazolidinyl)ethoxy)-2-(4-dimethylaminostyryl)benzofuran hydrochloride 

Relevant articles and documents

Synthesis and biological evaluation of novel shikonin-benzo[b]furan derivatives as tubulin polymerization inhibitors targeting the colchicine binding site

A novel series of shikonin-benzo[b]furan derivatives were designed and synthesized as tubulin polymerization inhibitors, and their biological activities were evaluated. Most compounds revealed the comparable anti-proliferation activities against the cancer cell lines to that of shikonin and simultaneously low cytotoxicity to non-cancer cells. Among them, compound 6c displayed powerful anti-cancer activity with the IC50 value of 0.18 μM against HT29 cells, which was significantly better than that of the reference drugs shikonin and CA-4. What's more, 6c could inhibit tubulin polymerization and compete with [3H] colchicine in binding to tubulin. Further biological studies depicted that 6c can induce cell apoptosis and cell mitochondria depolarize, regulate the expression of apoptosis related proteins in HT29 cells. Besides, 6c actuated the HT29 cell cycle arrest at G2/M phase, and influenced the expression of the cell-cycle related protein. Moreover, 6c displayed potent inhibition on cell migration and tube formation that contributes to the antiangiogenesis. These results prompt us to consider 6c as a potential tubulin polymerization inhibitor and is worthy for further study.

Synthesis and AChE inhibitory activity of N-glycosyl benzofuran derivatives

Six N-glycosyl benzofuran derivatives were synthesized by the catalysis of organic bases and condensation agents. The benzofuran derivatives were obtained by the reaction of various salicylaldehydes in acetone, and then hydrolyzed to the corresponding carboxylic acids. Finally, the target compounds were synthesized by acylation and the reaction conditions were optimized. The acetylcholinesterase (AChE) inhibitory activity of the desired compounds was tested using Ellman's method. Most of the compounds showed acetylcholinesterase-inhibition activity; N-(2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)benzofuran-2-carbxamide (5a) showed the best acetylcholinesterase inhibition, with an inhibitory rate of 84%.

Efficient synthesis of chiral benzofuryl β-amino alcohols via a catalytic asymmetric Henry reaction

Chiral β-amino alcohol ligands were found effective for the copper(ii)-catalyzed asymmetric Henry reaction of benzofuran-2-carbaldehydes with nitromethane, which led to the formation of (S)-enriched benzofuryl β-nitro alcohols with satisfactory enantioselectivities (up to 98% ee). Using this catalytic protocol, bioactive (S)-benzofuryl β-amino alcohols could be conveniently prepared in short steps.

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Human rhinoviruses (hRVs) are the main causative pathogen for common colds and are associated with the exacerbation of asthma. The wide variety in hRV serotypes has complicated the development of rhinovirus replication inhibitors. In the current investigation, we developed a novel series of benzothiophene derivatives and their analogues (6-8) that potently inhibit the replication of both hRV-A and hRV-B strains. Compound 6g inhibited the replication of hRV-B14, A21, and A71, with respective EC50 values of 0.083, 0.078, and 0.015 μM. The results of a time-of-addition study against hRV-B14 and hRV-A16 and resistant mutation analysis on hRV-B14 implied that 6g acts at the early stage of the viral replication process, interacting with viral capsid protein. A molecular docking study suggested that 6g has a capsid-binding mode similar to that of pleconaril. Finally, derivatives of 6 also displayed significant inhibition against poliovirus 3 (PV3) replication, implying their potential inhibitory activities against other enterovirus species.

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