17375-66-5

Usage

Uses

Used in Pharmaceutical Applications:
3-[2-(3,4-Dimethoxyphenyl)-7-methoxybenzofuran-5-yl]-1-propanol is used as a bioactive compound for its antibacterial and antifungal properties. The compound demonstrates potential in the development of new drugs to combat bacterial and fungal infections, particularly in cases where existing treatments may be less effective or have undesirable side effects.
Used in Agricultural Applications:
In the agricultural industry, 3-[2-(3,4-Dimethoxyphenyl)-7-methoxybenzofuran-5-yl]-1-propanol is used as a natural pesticide. Its antibacterial and antifungal properties make it a valuable tool for protecting crops from various diseases and pests, promoting healthier and more sustainable agricultural practices.
Used in Cosmetic Applications:
3-[2-(3,4-Dimethoxyphenyl)-7-methoxybenzofuran-5-yl]-1-propanol is also used as an active ingredient in the cosmetics industry. Its antimicrobial properties can be harnessed to create products with enhanced shelf life and improved safety profiles, particularly in formulations that are prone to microbial contamination.
Used in Research Applications:
In the field of scientific research, 3-[2-(3,4-Dimethoxyphenyl)-7-methoxybenzofuran-5-yl]-1-propanol serves as a valuable compound for studying the structure-activity relationships of benzofuran derivatives. Its unique chemical structure and biological activities make it an interesting subject for further investigation, potentially leading to the discovery of new therapeutic agents or applications in various industries.

InChI:InChI=1/C20H22O5/c1-22-16-7-6-14(11-18(16)23-2)17-12-15-9-13(5-4-8-21)10-19(24-3)20(15)25-17/h6-7,9-12,21H,4-5,8H2,1-3H3

Upstream product

• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 7359-14-0 2-hydroxy-5-iodo-3-methoxybenzaldehyde 
• 947232-07-7 2-(2,2-dibromovinyl)-6-methoxyphenol 
• 5034-74-2 5-bromo-3-methoxysalicylaldehyde 
• 35090-64-3 2-hydroxy-3-methoxy-5-bromobenzyl alcohol 
• 1218818-74-6 5-bromo-2-(3,4-dimethoxyphenyl)-7-methoxybenzofuran 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 93-07-2 Veratric acid 
• 5438-36-8 5-iodovaniline 
• 97-53-0 4-allylguaiacol 

Downstream Products

• 17375-67-6 3-[2-(3,4-dimethoxyphenyl)-7-methoxy-1-benzofuran-5-yl]propyl acetate 

Relevant academic research and scientific papers

Anti-complement activity of norlignans and terpenes from the stem bark of Styrax japonica

A new norlignan, styraxlignolide A (1), and two new terpenes, styraxosides A (2) and B (3), were isolated from the MeOH-soluble fraction of Styrax japonica Sieb. et Zucc. (Styracaceae) stem bark, together with two known compounds, egonol (4) and masutakeside I (5). The new compounds were determined as 5-(3″-hydroxypropyl)-7-methoxy-2-(3′,4′-dimethoxyphenyl) -benzofuran 3″-O-[β-D-xylopyranoside-(1→6)-β-D- glucopyranoside] (1), 3β,7β-dihydroxy-4α,4β,8β, 10β,14α-pentamethyl-5α-gon-16-en-2-one 3-O-[β-D- glucopyranoside-(1→2)-β-D-glucopyranoside] (2), and 3β,17β-dihydroxy-28-norolean-12-en-16-one 3-O-[α-L- rhamopyranoside-(1→2)-β-D-glucuronopyranoside] (3) by spectroscopic means including 2D-NMR. The five compounds were tested in vitro for anti-complement activity against the complement system. Compounds 1, 3, 4, and 5 displayed inhibitory activity in the anti-complement assay, with IC 50 values of 123, 65, 33, and 166 μM, respectively. Compound 1a and camellenodiol (3a), obtained from acid hydrolysis of 1 and 3, respectively, did not affect the hemolytic activity of human serum against sensitized erythrocytes. This shows that a sugar seems to play a role of enhancing significantly anti-complement activity.

Synthesis and Cytotoxicity Studies of Bioactive Benzofurans from Lavandula agustifolia and Modified Synthesis of Ailanthoidol, Homoegonol, and Egonol

2-Aryl/alkylbenzofurans, which constitute an important subclass of naturally occurring lignans and neolignans, have attracted extensive synthetic efforts due to their useful biological activities and significant pharmacological potential. Herein, we report a general and efficient approach to divergent 2-arylbenzofurans through a one-pot synthesis of versatile 2-bromobenzofurans as key intermediates. Using this approach, the first total synthesis of a series of trisubstituted and tetrasubstituted benzofurans bearing the hydroxyethyl unit, including the natural compounds isolated from Lavandula agustifolia (1-3) and their non-natural derivatives (4-8), was accomplished. We also report a modified synthesis of ailanthoidol, homoegonol, and egonol that enables the divergent synthesis of their derivatives for future exploration. Among these, the representative phenolic natural compound 2 and its derivatives 7 and 5 induced apoptotic cell death related poly(ADP-ribose) polymerase (PARP) cleavage in MCF74, A549, PC3, HepG2, and Hep3B cancer cell lines. Additionally, the tumor suppressor protein p53 was also induced in p53 wild type cancer cells.

A Convergent Total Synthesis of the Biologically Active Benzofurans Ailanthoidol, Egonol and Homoegonol from Biomass-Derived Eugenol

An efficient, general synthetic protocol for the synthesis of the biologically active benzofurans ailanthoidol, egonol and homoegonol was developed. The key starting material, eugenol, is a naturally occurring and abundant precursor. The protocol, involving sequential acylation and intramolecular Wittig reaction, provides a convenient method for building the benzofuran moiety in good yield.

NOVEL 2-PHENYLBENZOFURAN DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, PRODUCTION METHOD FOR SAME AND PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING INFLAMMATORY DISEASE COMPRISING SAME AS ACTIVE INGREDIENT

The present invention relates to a novel 2-phenylbenzofuran derivative or a pharmaceutically acceptable salt thereof, a production method for the same, and a pharmaceutical composition for preventing or treating an inflammatory disease comprising the same

An alternate method for the synthesis of 2-aryl/alkyl-5-bromo-7-methoxy benzofurans; application to the synthesis of Egonol, Homoegonol, and analogs via Heck reaction

We herein report the general, versatile, and convenient method for the synthesis of 2-arly/alkyl-5-bromo-7-methoxy benzofurans from easily available o-Vanillin in five steps. These benzofurans was successfully converted into biological active natural products Egonol, Homoegonol, and analogous on applying Heck reaction using ethyl/methyl acrylate in the presence of palladium catalyst.

Rapid Access to Benzofuran-Based Natural Products through a Concise Synthetic Strategy

A concise strategy is described for the synthesis of ailanthoidol (1), egonol (2), homoegonol (3), demethoxyegonol (4), demethoxyhomoegonol (5), and stemofuran A (6). This approach involves a Pd-catalysed domino cyclization/coupling process using triarylbismuth reagents for the generation of the benzofuran core. Subsequent structural modifications then give the final targets. The high yielding synthesis of the recently isolated natural products egonol-9(Z)-12(Z)-linoleate (2a), 7-demethoxyegonol-9(Z)-12(Z)-linoleate (4a), and 7-demethoxy-egonol-9(Z)-oleate (4b) are also reported.

Composition Containing Styraxlignolide A or the Aglycone Thereof as an Active Ingredient for Preventing or Treating Asthma

The present invention relates to a pharmaceutical composition for preventing or treating asthma, the composition containing styraxlignolide A or an aglycone thereof as an active ingredient. More particularly, styraxlignolide A compound is one separated fr

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.

Total synthesis of ailanthoidol, egonol, and related analogues

Efficient and general synthetic protocols were developed for the total synthesis of ailanthoidol, egonol, and some related analogues. The key transformations describe here involve a two-step construction of the benzofuran and a Sonogashira coupling, and proved to be convenient and effective, starting from readily available reagents.

Synthesis of Naturally Occuring 5-Allyl-2-aryl-7-methoxybenzofurans and 2-Aryl-5-(3-hydroxypropyl)-7-methoxybenzofurans

A convenient and general procedure is described for the synthesis of 5-allyl-2-aryl-7-methoxybenzofurans (8a-e) from 2-allyloxy-3-methoxybenzaldehyde (3).The compounds 8a and 8b on hydraboration followed by oxidation provide the naturally occuring benzofurans (1a and 1b)