• YAKHAK HOEJI
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• v.48 no.2
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• pp.135-140
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• 2004

For the development of new COX-2 inhibitors, 1,5-diarylhydantoins 5a∼5c and 1,5-diaryl-2-thiohydantoin 6a∼6c were synthesized from commercially available phenylacetic acids through esterification, bromination, C-N bond formation and cyclization. Esters 2a∼c were efficiently synthesized from the starting materials 1a∼c by refluxing in absolute methanol for 3 hours with catalytic concentrated sulfuric acid. Bromination of 2a∼c was carried out with use of N-bomosuccinimide at rt in dichloromethane. The bromine of 3a∼c was substituted with aniline in ethanol or N,N-dimethylformamide to provide 4a∼c. Hydantoins and 2-thiohydantoins were synthesized from 4a∼c by treatment of potassium isocyanate or potassium thiocyanate in dil-ethanol with triethylamine.

• Bulletin of the Korean Chemical Society
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• v.28 no.5
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• pp.751-757
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• 2007

To develop new COX-2 inhibitors, 1,5-diarylhydantoins and 1,5-diaryl-2-thiohydantoins were synthesized from phenylacetic acids by esterification, bromination, C-N bond formation and cyclization. Esters 1-3 were efficiently synthesized from the starting materials by reflux in absolute methanol for 3 h containing concentrated sulfuric acid as catalyst. Bromination was carried out with N-bromosuccinimide at rt in dichloromethane. Bromides 4-6 were reacted with aniline, p-anisidine, sulfanilamide in ethanol (or N,N-dimethylformamide) to provide the amines 7-15. Hydantoins and 2-thiohydantoins 16-46 were synthesized from amines 7-15 by treating them with potassium isocyanate (or potassium thiocyanate) and triethylamine. The synthetic process from alkyl α-anilinophenylacetate 7-15 to 3-alkylhydantoins was carried out in a one-pot reaction using alkyl isocyanate (alkyl isothiocyanate).

• Korean Journal of Clinical Pharmacy
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• v.16 no.1
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• pp.52-56
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• 2006

Aceclofenac, a nonsteroidal antiinflammatory agent of a phenylacetic acid type, has been used for rheumatoid arthritis and osteoarthrits. Although the metabolic pathway of aceclofenc is relatively well-known in vitro, pharmacokinetic profiles of its three major or metabolites are still unclear in human. The present study was designed to investigate pharmacokinetic profiles of the metabolites of aceclofenac, and to evaluate the bioequivalence of the generic preparation of aceclofenac 100 mg tablet. Blood samples were serially collected for a period of 12 hours following a single oral administration of 100 mg aceclofenac in 20 healthy human volunteers. A simple protein precipitation with acetonitrile was employed to purify those substances from plasma. Aceclofenac, diclofenac, 4'-hydroxyaceclofenac and 4'-hydroxy-diclofenac in heparinized plasma were simultaneously measured with flufenamic acid, an internal standard, using HPLC coupled to a tandem mass spectrometer. Time courses of 4'-hydroxydiclofenac, diclofenac and aceclofenac plasma concentrations were clearly revealed, and the pharmacokinetic properties were analyzed. The 90% confidence intervals for the ratios of test/reference for log-transformed AUC and $C_{max}$ lie within 0.80-1.25.

• The Plant Pathology Journal
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• v.29 no.2
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• pp.174-181
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• 2013

The plant growth-promoting rhizobacterium Ochrobactrum lupini KUDC1013 elicited induced systemic resistance (ISR) in tobacco against soft rot disease caused by Pectobacterium carotovorum subsp. carotovorum. We investigated of its factors involved in ISR elicitation. To characterize the ISR determinants, KUDC1013 cell suspension, heat-treated cells, supernatant from a culture medium, crude bacterial lipopolysaccharide (LPS) and flagella were tested for their ISR activities. Both LPS and flagella from KUDC1013 were effective in ISR elicitation. Crude cell free supernatant elicited ISR and factors with the highest ISR activity were retained in the n-butanol fraction. Analysis of the ISR-active fraction revealed the metabolites, phenylacetic acid (PAA), 1-hexadecene and linoleic acid (LA), as elicitors of ISR. Treatment of tobacco with these compounds significantly decreased the soft rot disease symptoms. This is the first report on the ISR determinants by plant growth-promoting rhizobacteria (PGPR) KUDC1013 and identifying PAA, 1-hexadecene and LA as ISR-related compounds. This study shows that KUDC1013 has a great potential as biological control agent because of its multiple factors involved in induction of systemic resistance against phytopathogens.

• The Journal of Korean Medicine
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• v.24 no.3
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• pp.23-34
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• 2003

Objective : In 2001, the rate of obesity in Korea reached 30.6%. There are many therapeutic ways to reduce body weight, such as low and very low calorie diet, exercise therapy, behavior modification therapy, etc. However, in many cases the patients feel stress under obesity treatment because of starvation. This study was aimed to evaluate the anti-starvation stress effect of Coicis Semen on mice. Methods : First, the mice were divided into 6 groups : Normal (group with no starvation), Control (administrated normal saline 6 times before starting 36 hours starvation), and Samples A, B, C, and D (administrated 0.25, 0.5, 1.0, 3.0 g/kg Coicis Semen respectively 6 times before starting 36 hours starvation). Then the plasma corticosterone level and rectal temperature were measured. The norepinephrine, dopamine, DOPAC (dihydroxy-phenylacetic acid), 5-HT (5-hydroxytryptamine) and 5- HIAA (5-hydroxy-indole-acetic acid) in the hypothalamus were measured by the HPLC method. Result : I. The rectal temperature in Sample group D showed a significant difference (P<0.05) compared with the Control group. 2. The DOPAC in Sample groups A, C and D showed the significant difference (P<0.05) compared with the Control group. Conclusion : It might be recognized that Coicis Semen has an anti-starvation stress effect.

• Archives of Pharmacal Research
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• v.21 no.1
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• pp.17-23
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• 1998

Flavonoid glycosides were metabolized to phenolic acids via aglycones by human intestinal microflora producing ${\alpha}$-rhamnosidase, exo-${\beta}$-glucosidase, endo- ${\beta}$-glucosidase and/or ${\beta}$-glucuronidase. Rutin, hesperidin, naringin and poncirin were transformed to their aglycones by the bacteria producing ${\alpha}$-rhamnosidase and ${\beta}$-glucosidase or endo- ${\beta}$-glucosidase, and baicatin, puerarin and daidzin were transformed to their aglycones by the bacteria producing ${\beta}$glucuronidase, C-glycosidase and ${\beta}$-glycosidase, respectively. Anti-platelet activity and cytotoxicity of the metabolites of flavonoid glycosides by human intestinal bacteria were more effective than those of the parental compounds. 3,4-Dihydroxyphenylacetic acid and 4-hydroxyl-phenylacetic acid were more effective than rutin and quercetin on anti-platelet aggregation activity. 2,4,6-Trihydroxybenzaidehyde, quercetin and ponciretin were more effective than rutin and ponciretin on the cytotoxicity for tumor cell lines. We insist that these flavonoid glycosides should be natural prodrugs.

• Journal of the Korean Society of Tobacco Science
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• v.25 no.2
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• pp.144-153
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• 2003

This study was carried out to determine the relationship between smoke components and sensory evaluation by changes tobacco leaf blending. Seven different cigarettes were made by adding different types of oriental, reconstituted and expanded tobacco leaves. 62 kinds of smoke components which were 6 of general components, 34 of semi-volatile and volatile components, 9 of acid components, and 13 of phenolic components were analyzed. Eight kinds of sensory item were evaluated and also electronic nose system data was collected. All smoke components and sensory characteristics of mainstream smoke were changed by the different blending. To determine the relationship between smoke components and sensory test, the correlation and regression analysis were carried out by using SPSS statistical program. Tar, pH, and CO showed a high correlation with sensory evaluation item. As tar related to hotness, CO have a high correlation with offensive aroma. Semi-volatile and volatile components of smoke related to sensory characteristics such as aroma, taste, irritation, hotness and smoothness. When propylene, l,3-butadiene, butane, isoprene, and 2-methylfuran showed a high correlation with aroma; methyl chloride, methanol, toluene, ethyl benzene showed a high correlation with irritation. Some acidic components and phenolic components of smoke also had a high relation to smoke volume. Especially the acidic components such as 2-furoic acid, 2-hydroxybutyric acid, phenylacetic acid and palmitic acid; the phenolic components such as 4-vinyl phenol, pyrocatechol, 3-methyl catechol, hydroquinone showed a high correlation with smoke volume. As using regression analysis, it was possible to estimate the results of sensory evaluation from the smoke analysis data. From the results of electronic nose system analysis, we can find the different pattern by adding expanded tobacco leaf.

• YAKHAK HOEJI
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• v.18 no.1
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• pp.59-73
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• 1974

Fifteen derivatives of phthalide were synthesized from m-hemipinic, hydrastic and 4,5-benzophthalic anhydride with acetic, phenylacetic, p-methoxyphenylacetic, p-nitrophenylacetic, ${\alpha}$-nephthylacetic and succinic acid by the Gabriel condensation. In the same way, 13 derivatives of phthalimidine and 4 derivatives of ${\alpha,\beta}$ -benzisothiazoline-1, 1-dioxide were synthesized from diphenylmaleimide, phthalimide, saccharine and 4,5-benzo-phthalimide with previous 6 acids. 3-Substituted derivatives of m-hemipinic anhydride, hydrastic anhydride and 4,5-benzophthalic anhydride were treated with formamide and seven 3-substituted imidines could be synthesized. In case of 4,5-benzophtha lide, two isomers,4,5-benzophthalidene-3-acetic acid and 4,5-benzophthalidene-1-acetic acid, can be obtained theoretically, but only one product we got, and the chemical structure of it was identified by the following way. It was hydrolyzed and then decarboxylated, and this decomposed product was identical with 1-acetyl-2-naphthoic acid which was synthesized from .betha.-naphthylamine. This indicates that by the Gabriel condensatioin 4,5-benzophthalide only produces 4,5-benzophthlidene-3-acetic acid, that is ${\alpha}$-carbonyl substitute.

• The Korean Journal of Ecology
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• v.24 no.3
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• pp.125-130
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• 2001

The allelopathic effects of aqueous extracts from Trifolium repens were studied. Aqueous extracts of leaves, stems, roots and flowers of T. repens strongly inhibited the seed germination and seedling growth of Zoysia japonica. In general, the higher concentration of the extracts showed the more great inhibition effect. The phenolic compounds extracted from T repens were analysed and identified using gas chromatography. 14 phenolic compounds were isolated from the leaves, stems, roots and flowers: caffeic acid, p-hydroxy benzoic acid, ferulic acid, gallic acid, p-coumaric acid, vanillic acid, trans-cinnamic acid, 2,5 dihydroxy benzoic acid, syringic acid, 2-hydroxy cinnamic acid, benzoic acid, salicylic acid, phloroglucinol and phanylacetic acid. The seed germination and relative growth ratio of Z. japonica by 14 phenolic compounds were inhibited in whole treatment. Stronger growth inhibitor were benzoic acid, salicylic acid and trans-cinnamic acid. From these results it is suggested that the phenolic compounds from T. repens seemed to be responsible for the allelopathic potential.

• The Korean Journal of Pharmacology
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• v.28 no.1
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• pp.11-18
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• 1992

Rats were treated with physostigmine, using 0.75 mg/kg acutely, with 0.75 mg/kg daily for 7 dats, or with 0.15 mg/kg/h continuously for 7 days. Striatal dopamine (DA), dihydroxyphenylacetic acid (DOPAC) and homovanillic acid (HVA) levels and tyrosine hydroxylase (TH) activities were studied. After acute treatment striatal DOPAC and HVA concentrations were significantly increased without changes in DA level 1 h, but not 24 h. And also the ratios of DOPAC/DA and HVA/DA were increased, suggesting an increased turnover of DA. however TH activities were decreased 24h, but not 1h after acute administration. After both daily and continuous treatment with physostigmine for 7 days, neither DA nor its metabolites were changed. However their ratios were decreased, suggesting a decreased turnover of DA. The TH activities were only decreased in the daily treated group, but not in the continously treated one. These results indicate that dopamine metabolisms are changed after acute and subacute administration with physostigmine. Further it suggest that the subacute stimulation of cholinergic activity may induce the dopamine metablism and activity to be decreased.