• Macromolecular Research
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• v.17 no.8
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• pp.557-562
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• 2009

The free radical polymerization of styrene was initiated with azobis(isobutyronitrile) in the presence of benzene sulfonyl chloride. Analysis of the terminal structures of the obtained polystyrene with $^1H$ NMR spectroscopy revealed the presence of a phenyl sulfonyl group at the ${\alpha}$-end and a chlorine atom at the ${\omega}$-end of each polystyrene chain. The terminal chlorine atom in the polystyrene chains was further confirmed through atom transfer radical polymerization (ATRP) of styrene and methyl acrylate using the obtained polystyrenes as macroinitiators and CuCl/2,2'-bipyridine as the catalyst system. GPC traces of the products obtained in ATRP at different reaction times were clearly shifted to higher molecular weight direction, indicating that nearly all the macroinitiator chains initiated ATRP of the second monomers. In addition, the number-average molecular weights of the polystyrenes increased directly proportional to the monomer conversions, and agreed well with the theoretical ones.

• Journal of the Korean Chemical Society
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• v.29 no.4
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• pp.426-436
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• 1985

Preparative and kinetic photochemical reactions of several benzanilides were studied. Several substituted benzanilides were synthesized by acylation of substituted anilines with substituted benzoyl chlorides. While benzanilide gave a photo-Fries type reaction product, 2-chlorobenzaniline, 2-bromobenzanilide, and 2-methoxybenzanilide gave a photocyclization reaction product, phenanthridone. Since 8-chlorophenanthridone was obtained from 2,2'-dichlorobenzanilide, the carbonyl phenyl is the excited site. Quantum yield of photocyclization of 2-chlorobenzanilide, 2'-chlorobenzanilide, and 2-methoxybenzanilide were obtained. 2-Chlorobenzanilide was photocyclized effectively and 2'-chlorobenzanilide ineffectively. Since the oxygen present in the reaction medium retarded the photocyclization reaction of 2-chlorobenzanilide, the triplet state of 2-chlorobenzanilide is involved. The mechanism of the photocyclization of 2-chlorobenzanilide is suggested: $\pi-complex$ between carbonyl phenyl and N-phenyl was formed from the triplet state of 2-chlorobenzanilide; neighbour phenyl (N-phenyl) assists for leaving of chlorine from carbonyl phenyl to make an intermediate, cyclized conjugated radical, because electron donating group on the N-phenyl ring accelerated the reaction; hydrogen detachment from the intermediate is obviously not a rate determined step because there was no isotope effect on the rate of photocyclization. The photocyclization reaction rate of 2-methoxybenzanilide was faster in the presence of oxygen than in the absence of oxygen. Thus, the singlet excited state of 2-methoxybenzanilide is involved in the reaction. Probably, the intermediate, methoxyhydro-phenanthridone is oxidized by oxygen in the medium to give phenanthridone.

• Natural Product Sciences
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• v.6 no.3
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• pp.135-138
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• 2000

MeOH extract of Cuscuta chinensis seeds was fractionated with n-hexane, EtOAc and BuOH successively, and antioxidant activities were tested for all fractions using DPPH free radical scavenging method. In the tested fractions, EtOAc fraction showed high antioxidant activity$(EC_{50},\;50\;{\mu}g)$ From the EtOAc fraction, five compounds have been isolated. On the basis of spectral data, these compounds were identified as ${\beta}-sitosterol$, methyl 4-hydroxy-3,5-dimethoxycinnamate, ${\beta}-sitosterol-3-O-{\beta}-D-glucopyranoside$, caffeic acid, quercetin, kaempferol and calycopteretin. Among these compounds, ${\beta}-sitosterol$ and ${\beta}-sitosterol-3-O-{\beta}-D-glucopyranoside$ showed no antioxidant activity. $EC_{50}$ values of methyl 4-hydroxy-3,5-dimethoxycinnamate, caffeic acid, quercetin, kaempferol and calycopteretin were 0.6, 8, 19, 17 and $12\;{\mu}g$, respectively.

• Journal of the Korean Chemical Society
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• v.18 no.5
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• pp.341-353
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• 1974

The electrochemical reduction of triphenylphosphine penylimide in nonaqueous media has been examined by polarography, cyclic voltammetry, controlled-potential coulometry and electron spin resonance spectroscopy. The reduction of triphenylphosphine phenylimide proceeds by a one-electron transfer to form anion radical which undergoes both protonation and a second one-electron reduction followed by cleavage of the phosphorus-nitrogen double bond. Aniline is a major product. The cleavage of a phosphorus-phenyl bond was also observed after reduction of triphenylphosphine oxide which is one of the major products of the chemical reaction which follow the primary process.

• Archives of Pharmacal Research
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• v.28 no.5
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• pp.518-528
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• 2005

In the present study, the antioxidative and inhibitory activity of Zingiber officinale Rosc. Rhizomes-derived materials (on mushroom tyrosinase) were evaluated. The bioactive co mponents of Z. officinale rhizomes were characterized by spectroscopic analysis as zingerone and dehydrozingerone, which exhibited potent antioxidant and tyrosinase inhibition activities. A series of substituted dehydrozingerones [(E)-4-phenyl-3-buten-2-ones] were prepared in admirable yields by the reaction of appropriate benzaldehydes with acetone and the products were evaluated in terms of variation in the dehydrozingerone structure. The synthetic analogues were examined for their antioxidant and antityrosinase activities to probe the most potent analogue. Compound 26 inhibited Fe$^{2+}$-induced lipid peroxidation in rat brain homogenate with an IC$_{50}$ = 6.3${\pm}$0.4 ${\mu}$M. In the 1,1-diphenyl- 2-picrylhydrazyl (DPPH) radical quencher assay, compounds 2, 7, 17, 26, 28, and 29 showed radical scavenging activity equal to or higher than those of the standard antioxidants, like ${\alpha}$-tocopherol and ascorbic acid. Compound 27 displayed superior inhibition of tyrosinase activity relative to other examined analogues. Compounds 2, 17, and 26 exhibited non-competitive inhibition against oxidation of 3,4- dihydroxyphenylalanine (L-DOPA). From the present study, it was observed that both number and position of hydroxyl groups on aromatic ring and a double bond between C-3 and C-4 played a critical role in exerting the antioxidant and antityrosinase activity.

• Journal of the Korean Chemical Society
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• v.25 no.6
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• pp.383-389
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• 1981

Thianthrene cation radical perchlorate reacts with N-arylsulfonamides such as p-toluenesulfonanilide, benzenesulfonanilide, N-(2-methylphenyl)benzenesulfonamide, and N-phenyl-p-toluenesulfonanilide to give 5-(p-N-p-toluenesulfonamidophenyl)-(1a), 5-(p-N-benzenesulfonamidophenyl)-(1b), 5-(4-N-benzenesulfonamido-3-methylphenyl)-(1c), and 5-(p-N-phenyl-N-p-toluenesulfonamidophenyl thianthrenium perchlorate (1d), respectively. In the meantime, 1d reacts further with thiathrene cation ratical to form diperchlorate(1e). The structure of 1a~1e is very similar to 5-(p-acetamidophenyl) thianthrenium perchlorate which has been obtained from the reaction with acetanilide. However, the discrepancy in the stoichiometry between two reactions indicates that the reaction with sulfonamide appears not to proceed with a single mechanism.

• 한국생물공학회:학술대회논문집
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• 2003.04a
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• pp.668-672
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• 2003

An antioxidative activity of Portulaca oleracea was tested by in vitro experimental models. The antioxidative activities were determined by evaluation the DPPH radical scavenging activity and by measuring lipid peroxide using 2-thiobarbituric acid (TBA). The crude extract was sequentially partitioned with n-hexane, 15% aq. MeOH, EtOAc, n-BuOH, $H_2O$. Among them, a remarkable antioxidative effect was observed in the fractions of EtOAc and n-BuOH. The DPPH radical scavenging effect $(IC_{50}=17.90{\mu}g/ml)$ of the n-BuOH soluble fraction was comparable with that of natural antioxidant, ${\alpha}-tocopherol(IC_{50}=\;6.99{\mu}g/ml)$ and the inhibitory effect of lipid peroxidation in mouse liver homogenate was similar to that of natural antioxidant, L-ascorbic acid at a concentration of 0.1mg/ml to 5mg/ml. From the BuOH soluble fraction yielded two biophenolic glycosides, 3-hydroxy-1-(2-hydroxyethyl)phenyl-4-O-${\beta}$-D-glucopyranoside(1) and 2-(3,4-dihydroxyphenyl)ethyl-O-${\beta}$-D-glucopyranoside(2) using column chromatography and revered-phase HPLC. In particular, the DPPH radical scavenging activity of 2 was comparable to that tocopherol$(IC_{50}=6.59{\mu}g/ml)$.

• YAKHAK HOEJI
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• v.47 no.4
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• pp.224-229
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• 2003

We have investigated the transport characteristics of synthetic antioxidant and free radical scavenger, $\alpha$-phenyl-n-tert-butyl nitrone (PBN) at the blood-brain barrier (BBB) by in vitro uptake study in conditionally immortalized rat brain capillary endothelial cell line (TR-BBB). Also, the efflux of PBN from brain to blood is estimated using the brain efflux index (BEI) method. Choline is a charged organic cation, including nitrogen-methyl group and shows the carrier-mediated distribution to the brain. [$^3$H]Choline uptake by TR-BBB cells was significantly inhibited by PBN with $IC_{50}$/ of 1.2 mM, which appears to be due to similar structures between choline and PBN. And, PBN was microinjected into Par2 of the rat brain by BEI method, and was eliminated from the brain with an apparent elimination half-life of about 2 min. Also, [$^3$H]choline efflux was significantly inhibited by PBN using BEI method. In conclusion, the efflux transport of PBN takes place across the BBB and PBN may be transported into the brain and eliminated from the brain by BBB choline transporter.

• Food Science and Biotechnology
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• v.17 no.6
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• pp.1376-1378
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• 2008

Tachioside (4-hydroxy-3-methoxy-phenyl-1-O-glucoside), a known phenolic glycoside, was isolated from various bamboo species. The 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity and Trolox equivalent antioxidant capacity determined a significant antioxidant activity of tachioside which was comparable to L-ascorbic acid. Each culm and leaf extracts were tested and the culm of Phyllostachys bambusoides appeared to contain the highest amount of tachioside.

• Journal of the Korean Chemical Society
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• v.43 no.1
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• pp.74-84
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• 1999

Most of the reactions involving benzotriazoles as a synthetic auxiliary have been explained by ionic mechanisms, whereas benzotriazole-mediated radical reactions have received little attention. The reaction of 1-[(aryl)(phenylseleno)methyl]benzotriazole with $Bu_3$SnH in the presence of AIBN in benzene at reflux gave 2-aminodiphenyl selenide (16-29%), 2-aminobiphenyl (9-15%), diphenyl diselenide (30-93%), 1-(arylmethyl) benzotriazole (9-39%) and tributyltin-phenyl selenide (10-36%), whereas the compounds were treated with excess molar amount of $Bu_3$SnH in the absence of AIBN to afford N-(arylmethyl)anilines (44-66%) along with diphenyl diselenide (53-100%), benzotriazole (27-35%) and 1-(arylmethyl)benzotriazole (16-33%). Similarly, treatment of 6-aryl-6-(benzotriazol-1-yl)-1-hexenyl phenyl selenides with $Bu_3$SnH in the presence of AIBN gave 6-aryl-6-phenylamino-1-hexene (9-31%) and 1-aryl-1-oxo-5-pentene (15-44%). A mechanism for the formation of the products is proposed.