• Archives of Pharmacal Research
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• 제25권6호
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• pp.786-789
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• 2002

The total synthesis of a norneolignan isolated from Ratanhia, 5-(3-hydroxypropyl)-2-(2'-methoxy-4'-hydroxyphenyl)benzofuran (8), is described. The key steps contain the one-pot reaction for a 2-arylbenzofuran 6 from methyl 3-(4-hydroxyphenyl)propionate with 2-chloro-2-methylthio-(2'-methoxy-4'-acetoxy)acetophenone (5) in the presence of $ZnCl_2$, and reductive desulfurization of the resulting product 6.

• Journal of Applied Biological Chemistry
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• 제58권4호
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• pp.295-301
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• 2015

Five phenylpropanoids (1-5), a benzofuran neolignan (6), two 8-O-4'-neolignans (7-8), and five tetrahydrofuran lignans (9-13) were isolated from a methanol extract of Myristica fragrans seeds. The structures of 1-13 were determined by $^1H$- and $^{13}C$-NMR spectroscopic data analyses and a comparison with the literature data. Compound 3 was isolated for the first time from this plant. All the isolated compounds were evaluated for their inhibitory activity against tyrosinase. Among them, safrole (1) showed significant inhibitions against both the monophenolase ($IC_{50}=32.11{\mu}M$) and diphenolase ($IC_{50}=27.32{\mu}M$) activities of tyrosinase. The kinetic analysis shows that safrole (1) is competitive inhibitors for both monophenolase and diphenolase. The apparent inhibition constant ($K_i$) for safrole (1) binding with free enzyme was determined to be 16.05 and $13.66{\mu}M$ for monophenolase and diphenolase, respectively.

• Bulletin of the Korean Chemical Society
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• 제35권7호
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• pp.1970-1972
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• 2014

A facile and efficient synthesis of dronedarone hydrochloride starting from commercially available 4-nitrophenol is described. This approach features a tandem-type synthesis of 3-carbonylated benzofuran involving cyclization of 2-ethynylphenol followed by $CO_2$ fixation at the 3-position of the benzofuran ring mediated by potassium carbonate without the addition of any transition metal catalyst.

• Journal of Photoscience
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• 제9권1호
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• pp.13-15
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• 2002

The structurally rigid $\alpha$-(o-alkylphenyl) acetophenone derivatives lacking $\beta$-hydrogens, 3,3-dimethyl-2-o-tolylibdan-1-one and 2-o-tolyl-benzofuran-3-one, were prepared and their photochemical behaviors were examined. The former did not give any photoproduct while the latter turned into its enol tautomer. The difference of reactivity of two ketones was attributed to aromatic character of the extol of the benzofuranone. It was concluded that the reaction occurred via photoinduced 1,3-H transfer.

• 한국작물학회지
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• 제51권4호
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• pp.295-297
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• 2006

Potassium (K) distribution in rice (Oryza sativa L.) root was studied by confocal laser microscopy, using potassium sensitive fluorescent dye potassium-binding benzofuran isophthalate (PBFI). Significantly high intensity of K-specific fluorescence was detected at the root cap region followed by meristematic and basal regions. A negligible or fainted fluorescence was observed at the root hairs area. These results suggest that K is heavily distributed in the apical area of rice root, which may be required in higher concentration for division and extension of cells, as it is the rapidly growing region of the root, moreover, may also be involved in water uptake by creating osmotic gradient across membranes.

• Archives of Pharmacal Research
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• 제23권5호
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• pp.438-440
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• 2000

The total synthesis of a demethoxy-egonol isolated from Styrax obassia, 5-(3-hydroxypropyl)-2-(3',4'-methylenedioxyphenyl)benzofuran (9), is described. The key steps involve the construction of a 2-arylbenzofuran skeleton 7 from methyl 3-(4-hydroxyphenyl)propionate with 2-chloro-2-methylthio-(3',4'-methylenedioxy) acetophenone (6) in the presence of ZnCl$_2$ and successive desulfurization of the resulting product 7.

• Archives of Pharmacal Research
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• 제27권1호
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• pp.19-24
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• 2004

The facile synthesis of a series of 2-(4-hydroxyphenyl)benzofurans (4a-e) is described. The one-pot reaction of 4-substituted phenols with the chloride 1 in the presence of zinc chloride afforded 3-methylthio-2-(4-acetoxyphenyl)benzofurans (2a-e). The compounds 4a-e were obtained from the hydrolysis of 2a-e followed by the desulfurization of the resulting 3-methylthio-2-(4-hydroxyphenyl)benzofurans (3a-e). 5-Methyl-3-p-toluoyl-2 -[4-(3-diethylaminopropoxy)phenyl]benzofuran (7), a $\beta$-amyloid aggregation inhibitor, was synthesized by three steps starting from 4a.

• 한국광과학회:학술대회논문집
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• 한국광과학회 2000년도 학술대회지
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• pp.26-26
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• 2000

• Bulletin of the Korean Chemical Society
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• 제17권3호
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• pp.295-299
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• 1996

• Natural Product Sciences
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• 제10권6호
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• pp.315-320
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• 2004

Alpha-viniferin was previously isolated as a cyclooxygenase (COX)-2 inhibitor from Carex humilis (Cyperaceae) and is an oligomeric stilbene compound with benzofuran (BF) moieties in its chemical structure. In the present study, a chemically synthetic BF compound, named as 3,3-dimethyl-2,3,4,6,7,8,9,10,11,12,13,14,15,16,17,18-hexadecahydro-1H-benzo[b] cyclopentadeca[d]furan-1-one, was discovered to inhibit bacterial lipo polysaccharide (LPS)-induced prostaglandin $E_2$ $(PGE_2)$ production in macrophages RAW 264.7. The BF compound exhibited a selectively preferred inhibitory effect on COX-2 activity over COX-1 activity. Furthermore, BF compound inhibited LPS-induced COX-2 expression at transcription level. As a down-regulatory mechanism of COX-2 expression shown by BF compound, suppression of nuclear factor $(NF)-{\kappa}B$ activation has been demonstrated. BF compound inhibited LPS-induced $NF-{\kappa}B$ transcriptional activity and nuclear translocation of $NF-{\kappa}B$ p65, in parallel, but did not affect LPS-induced degradation of inhibitory ${\kappa}B{\alpha}$ protein $(I{\kappa}B{\alpha})$. Taken together, anti-inflammatory effect of BF compound on $PGE_2$ production was ascribed by its down-regulatory action on LPS-induced COX-2 synthesis in addition to inhibitory action on enzyme activity of COX-2.