• Archives of Pharmacal Research
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• v.29 no.1
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• pp.16-25
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• 2006

A novel series of 1-(1-benzofuran-2-yl-ethylidene)-4-substituted thiosemicarbazides (2a-d) along with some derived ring systems: substituted-2,3-dihydro-thiazoles(3a-c, 4a-f) and thiazolidin-4-ones(5a-d and 6a-d), were synthesized. In addition, cyanoacetic acid-(1-benzofuran-2-yl-ethylidene) hydrazide(7) was used to prepare another new series of compounds consisting of substituted pyridin-2(1H)-ones(8a-c); 2-thioxo-2,3-dihydro-thiazoles(9a-d) and 2-thioxo-2,3-dihydro-6H-thiazolo[4,5-d]pyrimidin-7-ones (10a-c, 11a-c). The absolute configuration of compound 5c was determined by X-ray crystallography. The compounds prepared were evaluated for their in vitro anti-HIV, anticancer, antibacterial, and antifungal activities. Among the tested compounds, compounds 5c and 9a produced a significant reduction ㅐ ㄹ the viral cytopathic effect (93.19% and 59.55%) at concentrations $>2.0{\times}10^{-4}\;M\;and\;2.5{\times}10^{-5}\;M$respectively. Compound 9a was confirmed to have moderate anti-HIV activity. Compounds 2a, 2d, and 5c showed mild antifungal activity. However, none of the tested compounds showed any significant anticancer activity.

• Biomolecules & Therapeutics
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• v.23 no.3
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• pp.275-282
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• 2015

In the present study, we synthesized a series of novel 7-methoxy-N-(substituted phenyl)benzofuran-2-carboxamide derivatives in moderate to good yields and evaluated their neuroprotective and antioxidant activities using primary cultured rat cortical neuronal cells and in vitro cell-free bioassays. Based on our primary screening data with eighteen synthesized derivatives, nine compounds (1a, 1c, 1f, 1i, 1j, 1l, 1p, 1q and 1r) exhibiting considerable protection against the NMDA-induced excitotoxic neuronal cell damage at the concentration of $100{\mu}M$ were selected for further evaluation. Among the selected derivatives, compound 1f (with $-CH_3$ substitution at R2 position) exhibited the most potent and efficacious neuroprotective action against the NMDA-induced excitotoxicity. Its neuroprotective effect was almost comparable to that of memantine, a well-known NMDA antagonist, at $30{\mu}M$ concentration. In addition to 1f, compound 1j (with -OH substitution at R3 position) also showed marked anti-excitotoxic effects at both 100 and $300{\mu}M$ concentrations. These findings suggest that $-CH_3$ substitution at R2 position and, to a lesser degree, -OH substitution at R3 position may be important for exhibiting neuroprotective action against excitotoxic damage. Compound 1j was also found to scavenge 1,1-diphenyl-2-picrylhydrazyl radicals and inhibit in vitro lipid peroxidation in rat brain homogenate in moderate and appreciable degrees. Taken together, our structure-activity relationship studies suggest that the compound with $-CH_3$ substitution at R2 and -OH substitution at R3 positions of the benzofuran moiety might serve as the lead exhibiting potent anti-excitotoxic, ROS scavenging, and antioxidant activities. Further synthesis and evaluation will be necessary to confirm this possibility.

• Bulletin of the Korean Chemical Society
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• v.32 no.11
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• pp.4137-4140
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• 2011

• Journal of the Korean Chemical Society
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• v.42 no.6
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• pp.719-722
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• 1998

• Journal of the Korean Chemical Society
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• v.45 no.5
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• pp.500-504
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• 2001

• Journal of the Korean Chemical Society
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• v.44 no.5
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• pp.415-421
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• 2000

Volatile organic compounds(VOCs) emitted from PC/Monitor set and chemical parts com-prising of PC/Monitor set were analyzed aran, and xylene of VOCs based on qualitative analysis. As a result of these analyses, when the Wedge Rub-ber of rubber product was heated from 60$^{\circ}C$ to 80$^{\circ}C$, the emission rate(%) of xylene was increased about 2.5 times. But it was evaluated that the left of chemical parts were not affected by temperature except Wedge Rub-ber. The results of qualitative analyses between RGA and GC-MS were a little different respectively. With quantitative analysis, concentration of xylene emitted from cabinet was measured to be maximum as 6029.3 ug/ m$^3$(1.3ppm). The concentrations of toluene, xylene, and benzofuran derived from PC/Monitor set were 10.25${\mu}g/m^3$, 690${\mu}g/m^3$, and 180 ${\mu}g/m^3$, and these concentrations were relatively high levels which can bring on the risk to human health.

• Bulletin of the Korean Chemical Society
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• v.28 no.10
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• pp.1874-1876
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• 2007

• Korean journal of food and cookery science
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• v.17 no.6
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• pp.565-570
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• 2001

Soibirhym(Portulace oleracea) was extracted by methanol and its antimicrobial activities against food spoilage or foodborne disease microorganisms were investigated by the paper disc method. The microorganisms used in this experiment included 5 species of bacteria(Escherichia coli, Pseudomonas aeruginosa, Salmonella typhimurium, Klebsiella Pneumoniae, Staphylococcus aureus) and 3 species of fungi(Fusarium solani, Aspergillus flavius, Penicillium citreonigrum). Soibirhym showed high antimicrobial activites against P. citreonigrum, P. aeruginosa and K. pneumoniae. Minimum inhibitory concentrations(MICs) on S. aureus, P. citreonigrum and K. pneumoniae were 200, 200 and 250 mg/㎖, respectively. In the methanol extracts from Soibirhym, 147 kinds of compound were separated by GC/MS. The extraction yields of phenolics, furans, alcohols, acids and esters, ketones, aldehydes, and miscellaneous compounds were 7.43%, 6.13%, 2.20%, 41.06%, 9.21%, 0.15% and 1.08%, respectively. Some antimicrobial compounds such as 2,3-dihydro-benzofuran, 4-hydroxy-3-methoxy-benzoic acid, 4-hydroxy benzeneethanol were detected in the methanol extract.

• Biomolecules & Therapeutics
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• v.28 no.4
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• pp.344-353
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• 2020

This study aims to develop new potential therapeutic moracin M prodrugs acting on lung inflammatory disorders. Potential moracin M prodrugs (KW01-KW07) were chemically synthesized to obtain potent orally active derivatives, and their pharmacological activities against lung inflammation were, for the first time, examined in vivo using lipopolysaccharide (LPS)-induced acute lung injury model. In addition, the metabolism of KW02 was also investigated using microsomal stability test and pharmacokinetic study in rats. When orally administered, some of these compounds (30 mg/kg) showed higher inhibitory action against LPS-induced lung inflammation in mice compared to moracin M. Of them, 2-(3,5-bis((dimethylcarbamoyl)oxy)phenyl)benzofuran-6-yl acetate (KW02) showed potent and dose-dependent inhibitory effect on the same animal model of lung inflammation at 1, 3, and 10 mg/kg. This compound at 10 mg/kg also significantly reduced IL-1β concentration in the bronchoalveolar lavage fluid of the inflamed-lungs. KW02 was rapidly metabolized to 5-(6-hydroxybenzofuran-2-yl)-1,3-phenylene bis(dimethylcarbamate) (KW06) and moracin M when it was incubated with rat serum and liver microsome as expected. When KW02 was administered to rats via intravenous or oral route, KW06 was detected in the serum as a metabolite. Thus, it is concluded that KW02 has potent inhibitory action against LPS-induced lung inflammation. It could behave as a potential prodrug of moracin M to effectively treat lung inflammatory disorders.

• Journal of Microbiology and Biotechnology
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• v.9 no.6
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• pp.798-803
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• 1999

Prolyl endopeptidase [PEP; EC 3.4.21.26], a serine protease which is known to cleave peptide bonds on the carboxy side of a proline residue, plays an important role in the degradation of proline-containing neuropeptides that have been suggested to participate in learning and memory processes. An abnormal increase in the level of PEP, which can lead to generation of $A{\beta}$, is also suggested to be involved in Alzheimer's type senile dementia. In the course of screening PEP inhibitors from Basidiomycetes, the mushroom Polyozellus multiplex exhibited a high inhibitory activity against PEP. Two active compounds were isolated from the ethyl acetate soluble fraction by consecutive purification, using silica gel, Sephadex LH-20, and Lobar RP-18 chromatography. The chemical structures of these compounds were identified as thelephoric acid and 12-acety1-2,3,7,8-tetrahydroxy-[12H]-12-hydroxymethylbenzobis[I.2b,3.4b'] benzofuran-11-one (kynapcin-9) by spectral data including UV, IR, MS, HR-MS, $^1H-,{\;}^{13}C-$, and 2D-NMR. The $IC_{50}$ values of the thelephoric acid and kynapcin-9 were 0.157 ppm (446nM) and 0.087 ppm (212nM) and their inhibitor constants ($K_i$) were 0.73ppm ($2.09{\;}\mu\textrm{m}$) and 0.060 ppm (146 nM), respectively. Furthermore, they were non-competitive with a substrate in Dixon plots.