• YAKHAK HOEJI
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• v.36 no.1
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• pp.1-6
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• 1992

Irradiation of phenolbetaine in a stream of nitrogen produced 8,14-cycioberbine[1]. Compound[1] was treated with 10% HCl solution to give the 8-hydroxycycloberbine[2] in 67.7% yield. Subsequently addition of ethylchloroformate to the compound[2] gave rise to the 8-hydroxy-7-ethylcarboxy-9, 10-dimethoxy-2, 3-methylenelioxy-13-oxo-norochotensane[3] in 78% yield. Treatment of the compound[3] with bis-(2-chloroethyl)amine then lead to the 7-bis(2-chloroethyl)carbamyl-norochoteneare[4]. On the other hand the compound[5], which is the 8-methoxynorochotensane, was derived when compound[1] was treated with methanol in a few drops of BF. Treatment of the compound[6], and the compound[7], 7-bis(2-chloroethyl)-carbanyl-8-methoxy-norocheyensane, was then synthesized by reaction of the compound[6] with bis(2-chloroethyl) amine. In the other synthetic pathway when compound[5] was treated with $POCl_3$ in dried benzene, 13-chloro-6-ene-norochetensane[8] with 42% yield was formed. Finally the 13-bis-(2-chloroethyl) amino-8-methoxy-norochotensane[9] was produced when we treated the compound[8] with bis-(2-chloroethyl) amine. In another pathway, reaction between phenolbetaine which is the precursor of the compound[1] and benzoylchloride in dried chloroform gave us the 5,6,7 trihydro-2, 3-methylene-dioxy-9-chloromethyl-10, 11-dimethoxyphenylisoquinoline-8-benzoate[10] in 73% yield. The results of biological activities for these compounds are also presented in Table I and II.

• Applied Biological Chemistry
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• v.31 no.3
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• pp.234-240
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• 1988

Some chloroacetamide derivatives were synthesized from 2,6-dialkyl, aniline 4-chloroaniline, or 3,4-dichloroaniline with alkyl 2-bromopropionate and chloroacetyl chloride and identified by elemental analyses, NMR, and GC/MS spectra as N-(1'-methoxycarbonylethyl)-N-chloroacetyl-2,6-dimethylaniline(ACRI-S-8609), etc. These compounds synthesized were subjected to the test for pre-emergence herbicidal effecs on some grass weeds(Digitaria adscendens, Setaria viridis, Echinochloa crus-galli) and broad leaf weeds(Portulaca oleracea, Amaranthus lividus, Chenopodium album) in pots applied as wettable powder formulations. It was found that N-(1'-ethoxycarbonylethyl)-N-chloroacetyl-2,6-dimethylaniline(ACRI-S-8701) has the highest herbicidal effect on grass weeds, which corresponds to a 95% control effect at an application of 200g a.i/10a. Whereas, some chloroacetamide derivatives derived from 4-chloroaniline or 3,4-dichloroaniline had very weak herbicidal effects on grass and broad leaf weeds.

• Journal of the Korean Chemical Society
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• v.38 no.2
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• pp.108-121
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• 1994

The retention indices of branched-chain alkane, benzene ring, alcohol, amine, ketone, aldehyde and cyclic compounds were measured at 150, 180 and $210^{\circ}C$ on OV-1701 and OV-1 capillary columns. The group retention factors (GRF) of the substituents and the st` ructure retention factors (SRF) of the molecular structure change are derived from the retention indices of reference compounds and series of homologues. The $GRF_f$ equation of `f'th substituent is $GRF_f\;=\;I_{obs}-(100Z + \sum\limits_{i{\neq}f}GRF_i$ + {\sum}$SRF_i$)and the SRFf equation of `f'th molecular structure group is $SRF_f\;=\;I_{obs}-(100Z + {\sum}GRFi + \sum\limits_{i{\neq}f}SRF_i$). The predicted retention indices for those compound were in agreement, within the error of $\pm2$ and $\pm3%$, with the observed values that were obtained using the OV-1701 and OV-1 capillary column, respectively. The $\Delta$ xi of the substituents and $\Delta$ yi of the molecular structure change according to temperature change are derived from the $\Delta'/^{\circ}C$ of reference compounds and series of homologues. The $\Delta$ xi equation of the `f'th substituent is ${\Delta}x_f = {$\Delta}'/^{\circ}C+ \sum\limits_{i{\neq}f}\Delta$ xi + {\sum}{\Delta}yi\;and\;{\Delta}yi$ equation of the `f'th molecular structure group is ${\Delta}y_f$ = {\Delta}'/^{\circ}C+{\sum}{\Delta}xi +\sum\limits_{i{\neq}f}{\Delta}yi$. The predicted $\Delta'/^{\circ}C$ for these compounds were in agreement, within the error of ${\pm}18%$ and 17%, with the observed values that were obtained using the OV-1701 and OV-1 capillary column, respectively.

• Food Science and Preservation
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• v.22 no.6
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• pp.886-892
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• 2015

The antimicrobial effects of ten isothiocyanates (ITCs) present in cruciferous vegetables and radish root hydrolysate were investigated against pathogenic bacteria from olive flounder. Minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) were measured against two gram-positive bacterial strains (Streptococcus parauberis, S. iniae) and four gram-negative bacterial strains (Edwardsiella tarda, Vibrio ichthyoenteri, V. harveyi, Photobacterium damselae) by using a broth microdilution technique. The antibacterial activity of ITCs was in the order sulforaphane > sulforaphene > phenylethyl ITC > erucin > benzyl ITC > iberin > I3C > allyl ITC > phenyl ITC > hexyl ITC. The susceptibility of fish pathogens to ITCs was in the order of V. harveyi > E. tarda > P. damselae > S. parauberis > S. iniae > V. ichthyoenteri. Antimicrobial activity (MIC) of radish root hydrolysate was 0.250 mg/mL against S. iniae, 0.438 mg/mL against S. parauberis, and 0.500 mg/mL against both E. tarda and V. harveyi. The aliphatic ITCs were potent inhibitors of the growth of fish pathogens, followed by aromatic ITCs and indolyl ITC. The presence of a double bond in the chemical structure of ITCs decreased antibacterial activity, while ITCs with a thiol (-S-) group and a longer carbon chain increased antibacterial activity. These results suggest that ITCs have strong antibacterial activities and may be useful in the prevention of fish pathogens.

• Journal of the Korean Chemical Society
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• v.37 no.1
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• pp.119-130
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• 1993

The stereochemistry of 1,3-thiazolidine sulfoxides 1 in which 3 chiral centres are present in a molecule was elucidated by deuterium exchange and trapping reactions. 3-Acetoxy-1,3-thiazolidines 5 was oxidized to 6 and 8, corresponding $\alpha$-cis 10, $\alpha$-trans 11, $\beta$ -cis 12, and $\beta$ -trans 13 isomers were separated from their diasteromeric mixtures. Sulfoxide 10 was isomerized to more thermodynamically stable isomer 13 under neutral conditions in refluxing benzene or toluene. The methyl hydrogens of 2-methyl group in the sulfoxide 13 and those of the sulfoxide 11 were deuterated by the deuterium incorporation reactions. The intermediate sulfenic acids 25 and 26 derived from the sulfoxides 10 and 12 via sigmatropic rearrangement were trapped by 2-mercaptobenzothiazole (2-MBT) to give disufides 27 and 28 respectively. However, the sulfoxides 11 and 13 were transformed to ring expansion product dihydro-1,4-thiazine 29 under the same reaction conditions. In the presence of acid catalyst, the sulfoxides 10, 11, and 12 were converted to dihydro-1,4-thiazine 29 through the sulfoxide 13 quantitatively. The mechanisms of isomerization of sulfoxides and the formation of 29 were also discussed.

• YAKHAK HOEJI
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• v.51 no.2
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• pp.150-156
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• 2007

Some flavonoids have spasmolytic activities in various smooth muscles, but structure-activity relationships on their spasmolytic activity and its mechanism are unclear. In this study, effects of flavones (flavone and apigenin) and flavonols (quercetin and rutin) on the rat ileal smooth muscle contraction were studied in vitro and in vitro. In the electric stimulation-induced contraction, all of four flavonoids inhibited concentration-dependently the rat ileal smooth muscle contraction induced by electric stimulation (10 mV, 0.1 cps, 0.1 msec duration), IC$_{50}$ of quercetin, apigenin, flavone and rutin were 0.98${\times}$10$^{-5}$, 1.20${\times}$10$^{-5}$, 1.55${\times}$10$^{-5}$ and 1.85${\times}$10$^{-5}$ M, respectively. Flavonoids at a concentration of 2${\times}$10$^{-5}$ M also significantly inhibited the anaphylactic contraction and decreased concentration-dependently the mast cell degranulation by anaphylactic reaction, IC$_{50}$ of quercetin, apigenin, flavone and rutin were 4.0${\times}$10$^{-5}$, 7.5${\times}$10$^{-5}$, 8.0${\times}$10$^{-5}$ and 9.5${\times}$10$^{-5}$ M, respectively. These results indicated that flavones and flavonols inhibited the rat ileal smooth muscle contraction induced by electric stimulation because of their antagonism against acetylcholine and have spasmolytic activities on anaphylactic contraction which may be due to their mast cell-stabilizing activities. Furthermore, double bond of C$_{2,3}$ in benzene ring of flavonoids may be important in the their antispasmodic activities on the rat ileal smooth muscle contraction induced by electric stimulation and anaphylactic reaction.

• Polymer(Korea)
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• v.35 no.6
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• pp.505-512
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• 2011

Effects of structural features of 4 dinuclear constrained geometry catalysts having paraxylene derivative bridge (DCGC) on copolymerization of ethylene and 1-hexene were investigated. The bridges of three catalysts have para-xylene backbone with a different substituent at benzene ring. The substituents were hydrogen (Catalyst 1), isopropyl (Catalyst 2), n-hexyl (Catalyst 3) and 1-octyl (Catalyst 4). It was found that Catalyst 1 having hydrogen as a substituent exhibited the greatest activity among the four dinuclear CGCs. On the other hand, Catalyst 2 containing isopropyl as a substituent showed the smallest activity. Very interestingly, Catalyst 2 was able to produce about 6 times higher molecular weight polymer than Catalyst 3 and 4. Catalyst 3 and 4 having a long alkyl chain substituent revealed the biggest comonomer response to generate polyethylene copolymer containing more than 40% 1-hexene contents. These results suggest that the control of the substituent of para-xylene bridge of dinuclear CGC can provide a proper method to adjust the microstructure of polyethylene copolymers.

• Bulletin of the Korean Chemical Society
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• v.14 no.6
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• pp.687-691
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• 1993

Complexation of $Cd^{2+},\;Pb^{2+}\;and\;Hg^{2+}$ ions with four cryptands were studied by potentiometry and solution calorimetry in various weight percent methanol-aqueous solvent at 25${\circ}$C under $CO_2$free nitrogen atmosphere. The stabilities of the complexes were dependent on the cavity size of macrocycles. The $Hg^{2+}$ ion stability constants are higher than those of $Cd^{2+}\;and\;Pb^{2+}$ ion. All the cryptands formed complexes having 1 : 1 (metal to ligand) mole-ratio except for $Hg^{2+}-L_1$ (cryptand 1,2b: 3,5-benzo-9,14,17-trioxa-1,7-diazabicyclo-(8,5,5) heptadecane) and $Cd^{2+}-L_2$ (cryptand 2,2b: 3,5-benzo-10,13,18,21-tetraoxa-1,7-diazabicyclo (8,5,5) eicosane) complexes. $Hg^{2+}-L_1$ complex was a sandwitch type, and the $Cd^{2+}-L_2$ complex showed two stepwise reactions. Thermodynamic parameters of the $Cd^{2+}-L_2$ complex were $6.08(log\;K_1)$, -7.28 Kcal/mol $({\Delta}H_1)$, and $4.78\;(log\;K_2)$, -4.62 Kcal/mol $({\Delta}H_2)$, respectively, for 1 : 1 and 2: 1 mole-ratio. The sequences of the selectivity were increased in the order of $Hg^{2+}\;>Pb^{2+}\;>Cd^{2+}$ ion for $L_3\;and\;L_4$ macrocycles, and the $L_2$-macrocycle has a selectivity for $Cd^{2+}$ ion relative to $Zn^{2+},\;Ni^{2+},\;Pb^{2+}\;and\;Hg^{2+}$ ions. Thus, it is expected that the $L_2$ can be used as carrier for seperation of the post transition metals by macrocycles-mediated liquid membrane because $L_2$ is not soluble in water, and the difference of stability constants of the metal complexes with $L_2$ are large as compared with the other transition metal complexes. The $^1H\;and\;^{13}C-NMR studies indicated that the nitrogen atoms of cryptands have greater affinity to the post transition metal ions than the oxygen atoms, and that the planarities of the macrocycles were lost by complexation with the metal ions because of the perturbation of ring current of benzene molecule attached to macrocycles and counter-anions.

• Journal of Soil and Groundwater Environment
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• v.19 no.6
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• pp.59-71
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• 2014

We investigated soil contamination depending on the land use by examining the contamination levels and distribution characteristics of 16 polycyclic aromatic hydrocarbons (PAHs) in the national soil. Total PAHs (the sum of 16 PAH concentrations) and carcinogenic PAHs (the sum of seven carcinogenic PAH concentrations) were $8.50{\sim}3,437.16{\mu}g/kg$ and $2.94{\sim}2,136.96{\mu}g/kg$, respectively. The concentration of benzo(a)pyrene, one of the contaminants regulated by the soil quality standard in the nation, was $ND{\sim}924.73{\mu}g/kg$. Its maximum value of $924.73{\mu}g/kg$ was detected in railroad (Region 3) and is approximately 13% of the standard value for Region 3 (i.e., 7 mg/kg). We also investigated the characteristics of contamination sources of PAHs in soil of the upland, forests, roads, and railroads, examining the fraction distribution of PAHs concentration by the number of benzene rings against the total PAHs concentration. The results demonstrate that the mean fraction of 4~6-ring PAHs against total PAHs concentration in soil was in the range of 51.8~80.7% with relative abundance of high-molecular PAHs, showing that the origin of contamination is under the category of combustion sources. When the molecular indices (Flu/(Flu/Pyr), Ant/(Ant+Phe), InP/(InP+BP), and BaA/(BaA+Chr)) were applied, they were also categorized as petroleum-based combustion sources. The individual PAH concentrations in soil by the land use were grouped into Regions 1, 2, and 3, which are statistically treated and are the parts of the national category system of soil quality standard. As a result, the concentration level of 16 PAHs was $0.02{\sim}2.63{\mu}g/kg$ in Region 1, $0.05{\sim}4.26{\mu}g/kg$ in Region 2, and $2.36{\sim}178.27{\mu}g/kg$ in Region 3. The concentration level of 6 carcinogenic PAHs was 14.2~320.4% against that of benzo(a)pyrene in Region 3 and sites of recycling waste sleepers. Considering that there were similarities among PAHs in terms of structures and toxicities, it would be recommended to review other types of carcinogenic PAHs together with benzo(a)pyrene when developing the soil quality standards in the nation.

• Journal of the Society of Cosmetic Scientists of Korea
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• v.48 no.2
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• pp.135-146
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• 2022

In order to prevent microbial contamination and safely use cosmetics, it is essential to possess preservative power. In this study, the antifungal effect was confirmed by improving the preservative system of the aqueous dispersion formulation, which has a weak preservative power against fungi, and various preservative systems were established to strengthen the preservative power against fungi. Five kinds of raw materials (sodium anisate, p-anisic acid, caprylhydroxamic acid, o-cymen-5-ol, hydroxyacetophenone) that have a benzene ring structure having a hydroxyl group and exist as protonated form in cosmetic formulations expected to improve antifungal activity in cosmetics were selected, and the minimum growth inhibitory concentration of the raw materials was determined through MIC assay. It was confirmed that the preservative power against mold was improved through the preservative efficacy test of 4 types of water dispersion formulations (cream, lotion, toner, and sun cream) in which 4 types of raw materials showing antimicrobial activity against mold were added to the preservative system. When p-anisic acid was used, it was confirmed that the preservative activity against mold was strengthened without the effect of inhibiting the preservative power against bacteria and yeast in all four formulations.