• Korean Chemical Engineering Research
• /
• v.43 no.6
• /
• pp.662-667
• /
• 2005

2,3-Dihydrobenzofuran derivatives, important intermediates of medicines and agricultural chemicals, were prepared from aryl methallyl ethers over MCM-41 mesoporous material catalysts. Two mesoporous materials with Si/Al mole ratios of 40 and 50 were prepared to investigate the effect of acid site concentration on their catalytic activities. Aryl methallyl ethers with various substituents on their benzene rings were used to investigate the effect of electron density on benzene ring on the conversion of the ethers and the yield of 2,3-dihydorbenzofuran derivatives. The catalyst with a high acid site concentration showed high conversions, but it is difficult to correlate the yield of the derivatives with the acid site concentration. The increase in the electron density of the benzene ring by introducing electron-donating groups accelerated Claisen rearrangement reaction, resulting in the enhanced yield of the derivatives. On the other hand, the decrease in the electron density by introducing electron-attracting groups accelerated the cracking reaction of aryl methallyl ether by acid catalysts, producing phenol derivatives rather than 2,3-dihydrobenzofuran derivatives.

• Archives of Pharmacal Research
• /
• v.22 no.3
• /
• pp.306-308
• /
• 1999

The oxidative dimerization of ferulic acid has been carried out using horse-radish peroxidase as catalyst to give a dihydrobenzofuran neolignan (1), the structure of which was elucidated as (2SR, 3RS)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3n-butoxycarbonyl-5-(2E-carboxyethenyl)-7methoxybenzofuran by spectroscopic analyses. This compound showed more potent cytotoxicity against several tumor cell lines than the starting material.

• Bulletin of the Korean Chemical Society
• /
• v.32 no.3
• /
• pp.1083-1086
• /
• 2011

• Archives of Pharmacal Research
• /
• v.16 no.4
• /
• pp.343-346
• /
• 1993

A new method was described for the preparation of 7-[p-(methylthio)benzoyl]-5-benzofuranacetic acid 6, which is an analgestic agent. Methyl 5-(2, 3-di-hydobenzofuran)acetate 3 was obtained by Friedel-Crafts reaction of 2, 3-dihydrobenzofuran with methyl .alpha.-chloro-.alpha.(methylthio)actate 1 and desulfurization of 2. Tifurac 6 was synthesized from acylation of 3 with p-(methythio)benzoyl chioride followed by bromination of 4, dehydrohalogenation, and hydrolysis of 5.

• Bulletin of the Korean Chemical Society
• /
• v.22 no.2
• /
• pp.139-140
• /
• 2001

• Bulletin of the Korean Chemical Society
• /
• v.26 no.9
• /
• pp.1440-1442
• /
• 2005

• Bulletin of the Korean Chemical Society
• /
• v.25 no.11
• /
• pp.1726-1728
• /
• 2004

• Natural Product Sciences
• /
• v.22 no.1
• /
• pp.53-59
• /
• 2016

Anti-inflammatory effects of dihydrobenzofuran neolignans isolated from Euonymus alatus leaves and twigs were evaluated in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells. Six neolignans, (+)-simulanol (1), (+)-dehydrodiconiferyl alcohol (2), (-)-simulanol (3), (-)-dehydrodiconiferyl alcohol (4), (+)-dihydrodehyrodiconiferyl alcohol (5), threo-buddlenol B (6) effectively inhibited the production of nitric oxide (NO) induced by LPS, and the activity of iNOS. (-)-dehydrodiconiferyl alcohol (4), which showed the most potent inhibitory activity, attenuated the activity of iNOS enzyme and also the expression of iNOS and COX-2 proteins. The subsequent production of pro-inflammatory cytokines, interleukin-$1{\beta}$, interleukin-6, tumor necrosis factor-${\alpha}$ and prostaglandin E2 were also inhibited by the pretreatment of RAW264.7 cells with (-)-dehydrodiconiferyl alcohol (4). These neolignans are thought to contribute to anti-inflammatory effects of E. alatus, and expected to be potential candidates to prevent/treat inflammation-related diseases.

• Korean Journal of Food Science and Technology
• /
• v.22 no.5
• /
• pp.549-554
• /
• 1990

Glycosidically bound fraction was separated from apricot by Amberlite XAD-2 adsorption and eluted with methanol. Aglycones were liberated from the bound fraction by enzymatic hydrolysis, acid hydrolysis or by means of simultaneous distillation-extraction at pH 3.0. A total of 40 components were identified in three bound volatile fractions. Besides linalool oxide, linalool. ${\alpha}-terpineol$, nerol, geraniol, benzyl alcohol and 2-phenylethyl alcohol, previously reported as glycosidically bound volatiles, the following components were identified for the first time as glycosidically bound volatiles in apricot: 2,6-dimethyl-3,7-octadiene-2,6-diol , 3.7-dimethyl-1,5-octadiene-3,7-diol, (E)- and (Z)-2.6-dimethyl-2,7-octadiene-1,6-diol, $3,4-didehydro-{\beta}-ionol,\;3-oxo-{\alpha}-ionol$, $3-hydroxy-7,8-dihydro-{\beta}-ionol,\;3-oxo-7,8-dihydro-{\alpha}-ionol ,\;3-hydroxy-{\beta}-ionone$, eugenol, 4-hydroxyethylphenyl acetate and 2,3-dihydrobenzofuran.

• The Korean Journal of Pesticide Science
• /
• v.12 no.1
• /
• pp.9-17
• /
• 2008

QSARs (Quantitative structure-activity relationships) between a series of new cyclohexanedione derivatives (5-benzofuryl-2-[1-(alkoxyimino)-alkyl]-3-hydroxycyclohex-2-en-1-ones) and their herbicidal activity against Rice plant (Oryza sativa L.) and Barnyard grass (Echinochloa crus-galli.) were discussed quantitatively using 2D-QSAR and holographic (H) QSAR methods. Generally, the HQSAR models have better predictability and fitness than the 2D-QSAR models. The herbicidal activities against Barnyard grass with 2D-QSAR II model were dependent upon Balaban indice (BI) of molecule and hydrophobicity of $R_1$ and $R_3$ group. And also, the $R_3=ethyl$ group, according to the information of the optimized HQSAR IV model, was more contribute to the herbicidal activities against Rice plant, while the 5-(cyclohex-3-enyl)-2,3-dihydrobenzofuran ring part was not contribute to the herbicidal activities against two plants.