• Bulletin of the Korean Chemical Society
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• v.34 no.8
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• pp.2297-2304
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• 2013

A series of novel benzimidazole derivatives bearing a heterocyclic ring as oxadiazole (21-32), thiadiazole (33-34), triazole (35-36) were synthesized and evaluated for their activities against Coxsackie virus B3 and B6 in Vero cells. Compounds 21-26, 31-36 with moieties of 2'-pyridyl, 3'-pyridyl and 4'-pyridyl at the 2-position and oxadiazoles, thiadiazole, or triazole substituent at the 4- or 5-position generally displayed activities against CVB3 and CVB6. Especially compound 24 ($IC_{50}=1.08{\mu}g/mL$, SI = 61.7 against CVB3) was the promising candidate as lead compound for anti-enteroviral drug. It was observed in the incorporation of heterocyclic rings in benzimidazole at the 5-position could enhance their biological activities.

• Journal of Photoscience
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• v.3 no.2
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• pp.91-93
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• 1996

In connection with our interest on the photochemical properties of heteroaryl halides, which are currently the subject of heterocyclic ring formation and haloarene degradation, we have studied the photochemistry of the haloarene linked to N-heteroarene compounds. Imidazo[5,1-a]isoindole was synthesized from N-(ochlorobenzyl)imidazole or N-(o-bromobenzyl) imidazole in acidic aqueous solution or acetonitrile via the intramolgcular photocyclization (Table 1). This type of reaction provides the synthetic methods for 5- and 6-membered polyheteroatomic heterocyclic ring compounds. However, the reaction mechanism for the intramolecular photocyclization of haloarene tethered heteroarenes has not yet been established. Grimshaw et al. suggested a mechanism for homolyric carbonhalogen bond fission assisted by radical complexation to explain their results in the photocyclization of 5-(2-chlorophenyl)-1,3-diphenylpyrazole. They also reported the detection of acyclohexadienyl intermediate involved in the above reaction. Park et al. reported several transient 'intermediates involved in the laser flash photolysis of N-(o-halobenzyl) pyridinium and N-benzyl-2-halopyridinium salts. Thus we performed the laser flash photolysis study on the photocyclization reaction of N-(o-chlorobenzyl) imidazole to identify the intermediate species involved in the reaction. Here, we report on the preliminary results in the photocyclization reaction of N-(o-halobenzyl)imidazole through the detection of reaction intermediates.

• Journal of the Korean Society of Food Science and Nutrition
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• v.25 no.4
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• pp.617-626
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• 1996

Nitrogenous compounds in hydrolysate of skipjack processing by-product(SPB) was increased 6.4 times in amount comparing that of raw SPB. The major compounds in hydrolysate were anserine, histidine, leucine, hydroxyproline, arginine, phenylalanine and taurine, and composed 56.25% of total nitrogenous compounds. In fatty acid composition, the highest amount was saturated fatty acids in both samples. Polyunsaturated fatty acids such as $C_{20:5}$ and $C_{22:6}$ were increased after hydrolysis. A total of 99 volatile compounds was detected in raw and hydrolysate of SPB by vacuum simultaneous steam distillation-solvent extraction/gas chromatography/mass chromatorgraphy. Of these, 75 compounds were identified in raw SPB, while 72 compounds were identified in hydorlysate of SPB. There compounds were composed mainly of 28 aldehydes, 20 ketones, 19 alcohols, 5 nitrogen containing compounds, 5 aromatic hydrocarbons, 4 furans and 12 miscellaneous compounds. Levels of aldehydes and aromatic hydrocarbons decreased after hydrolysis, whereas heterocyclic compounds such as pyrazies, furans increased.

• Bulletin of the Korean Chemical Society
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• v.31 no.5
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• pp.1305-1308
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• 2010

Regioselective perfluorinated isoxazolidine (5 and 7), isoxazoline (9) and 1,2-addition products (6 and 8) having a long alkyl chain functionality have been prepared by 1,3-dipolar cycloaddition between a 1,3-dipole (NH-nitrone or nitrile oxide) and dipolarophile (perfluoro-2-methyl-2-pentene or styrene), respectively. Interestingly, unusual extended conjugated form of isoxazoline adduct (10) was obtained by dehydrofluorinated reaction from the corresponding perfluorinated isoxazoline adduct (9) which was derived from cycloadition between the perfluorinated long alkyl nitrile oxide 1,3-diplole and styrene olefin. This synthetic methodology of heterocyclic compound having a long alkyl chain functionality is useful for the designing of synthetic strategy and potential self-assembled monolayers (SAM) application. These derivatives were characterized by IR, $^1H$ and $^{19}F$ NMR, and MASS analysis.

• Elastomers and Composites
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• v.12 no.1
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• pp.27-32
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• 1977

The kinetics of azo-coupling reaction of N-acetyl-H-acid (1-acetamino-8-hydroxynaphthalene-3, 6-disulfonic acid) with several heterocyclic diasonium compounds such as diazotiged 3-aminopyridine, 3-aminoquinoline, 8-aminoauinoline and aniline was studied. It was found that reactions proceeded at remarkably different rate. Reaction rate was in increasing order; 3-aminopyridine, 3-aminoquinoline, 8-aminoauinoline and aniline. And the activation energies were 9.62, 10.10, 10.39, 10.70 Kcal/mole, respectively. Especially, the rate constant of 3-aminopyridine was 100 times larger than that of benzene diasonium compound even in strong acidity. Hammett plot was also made of the rate constants obtained against the heterocyclic substituent constants reported in the literature. A good linear relationship was obtained and the reaction constant of N-acetyl H-acid was calculated to be 3.14.

• Archives of Pharmacal Research
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• v.13 no.1
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• pp.24-27
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• 1990

Reaction of 2-formyl-4H-thieno [2, 3-b] benzothiopyran-4-one (1) with different heterocyclic amines afforded the corresponding Schiff's bases (2-4). Diethyl malonate, ethyl cyanoacetate and malononitrile were reached with 1 to afford compounds 5, 7 and 8, respectively. Compound 5 was cyclized to the pyrazolidin-3, 4-dione (6) by the action of hydrazine hydrate, whereas compound 7 was utilized for the synthesis of the thiazolin-4 one derivatives (9-13).

• The Korean Journal of Food And Nutrition
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• v.17 no.3
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• pp.313-321
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• 2004

Separation-concentration of sulfur containing heterocyclic compounds(SCHC) from many reaction meat flavors manufactured with Maillard reaction was carried out. Profile of SCHC was identified and analyzed by GC and GC-MSD. The results were as follows. 1. Profile of SCHC could be identified 7 kinds thiazole and 11 kinds thiophene, the major produced compounds were thiophene, thiazolidine, 4-methyl-5-thiazole ethanol. 2. In the case of SCHC, relationship between changes of reaction conditions and the kind of produced components were as same, but produced amounts appeared the difference. Producing amount of complexed SCHC and caramellike note as well as oxygen containing heterocyclic compounds were high level more than high reaction temperature and long time reaction period. 3. Producing ratio of comparative simple structural SCHC were the highest level at reaction conditions of moisture content 50%, reaction temperature 100$^{\circ}C$ and reaction time 2 hours. Reaction conditions for the revelation of reaction meat flavor were below 110$^{\circ}C$ and less than 2 hours. 4. Relationship between moisture content and reaction temperature as well as reaction time had very relative relation. From the change of moisture content and reaction conditions could be obtained the simultaneously profile. Signal presentation for production of reaction meat flavor could be from extraction-separation-concentration of SCHC through simplification of raw-materials in the flavor and seasoning food industry.

• Journal of the Korean Society of Food Science and Nutrition
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• v.30 no.6
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• pp.1033-1037
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• 2001

Garlic oleoresins were made by extracting with four solvents of methanol, methyl acetate hexane and acetone from chopped garlic, respectively, and the volatile compounds of each extract were separated by gas chromatography installed with polar (supelcowax-10$^{TM}$) and nonpolar (HP-5) capillary columns, respectively, and identified by matching mass data of mass selective detector and Kovat\`s retention index with references. The numbers of the volatile compounds identified the garlic oleoresin by polar and nonpolar columns from in garlic oleoresins were 41 and 32, respectively. In polar column, 13 pyrans, 11 sulfur-containing compounds 6 furans 2 alcohols and 2 heterocyclic compounds were identified. In nonpolar column, 11 sulfur-containing compounds 5 acids 3 furans and eugenol were identified. The major sulfur-containing compounds identified from the oleoresins were 3, 3'-thiobis-1-propene, methyl 2-propenyl disulfide, dimethyl trisulfide, di-2-prnpenyl-trisulfide, 2-thiophenecarboxylic acid. The amount of these sulfur-containing compounds isolated from the oleresins were more abundant in polar column than in nonpolar column. The most efficient solvent for extracting volatile compounds of garlic was methanol but the most useful solvent for extracting sulfur-containing compounds was methyl acetate of less polarity.y.

• KSBB Journal
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• v.26 no.2
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• pp.177-181
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• 2011

This study was conducted to investigate the effects of gamma irradiation on the change of volatile flavor compounds of raw oyster and its cooking drips using headspace methods. Major volatile flavor compounds of the raw oyster were identified as methylthiomethane and 1,5-hexadiene. When the raw oyster was irradiated at the dose of 5 kGy, 1-pentane was newly detected. On the other hand, 9 compounds including N-methoxyformaldehyde were identified as the major volatile compounds of cooking drips from oyster. Among them, N-methoxyformaldehyde contents in cooking drip was decreased by the gamma irradiation. By the gamma irradiation above 30 kGy, new heterocyclic compounds was found in oyster cooking drips. Therefore, the amount of volatile flavor compounds in the raw oyster and cooking drips were changed by gamma irradiation, and these results could be potentially used in the seasoning industry.

• The Korean Journal of Pesticide Science
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• v.9 no.2
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• pp.181-184
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• 2005

The heterocyclic PPO inhibitor compounds have been studied due to their potent herbicidal effects without toxic to human and animals. We have designed and synthesized 4,5,6,7-tetrahydroindazole, maleimide, and tetrahydrophthalimide compounds carrying diverse epoxide substituents at 5- position of the phenyl group. Their herbicidal activities were evaluated under submerged paddy conditions. These results showed that 4,5,6,7-tetrahydroindazole compounds gave potent herbicidal activities especially to ECHOR, MOOVA, and CYPSE at a relatively low rate of 16 g/ha and improved tolerance on rice compared to S-275 as a standard herbicide in this experiment.