• Journal of the Korean Society of Tobacco Science
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• v.25 no.2
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• pp.160-166
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• 2003

The majority of ι-menthol is still obtained by freezing the oil of Mentha arvensis to crystallize the menthol present. This 'natural' menthol is then physically seperated by centrifuging the supernatant liquid away from the menthol crystal. But the price of natural ι-menthol has fluctuated widely so effort has been devoted to the production of ι-menthol by synthetic more readily available raw materials. In the 1970's, many researcher synthesised a new compounds with the menthol cooling effect. During this period many molecular structure designed and synthesised on concepts of correlation between structure and biological activity and the various types of molecule which give rise to cooling effect more than ι-menthol. Specially, N-alkyl-carboxamide group is substituted for the hydroxyl group in ι-menthol. Recently, the most active compounds synthesised is 4-methyl-3-(1-pyrrolidinyl)-2-[5H]-furanone. This compound is 35 times more powerful in the mouth and 512 times more powerful on the skin than ι-menthol. The cooling effect also lasts twice as long. While not yet commercially available, it is expected that these types of materials will be subjected to toxicological studies and will soon be sell on the market.

• Archives of Pharmacal Research
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• v.21 no.4
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• pp.452-457
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• 1998

Three compounds, 5-(acetoxymethyl)-5-(hydroxymethyl)-3-tetradecyl-2,5-dihydro-2-furanone (3), 5-(acetoxymethyl)-5-(hydroxymethyl)-3,3-dihexyltetrahydro-2-furanone (4) and 5-(acetoxymethyl)-5-(hydroxymethyl)-3,3-dioctyltetrahydro-2-furanone (5), were designed and synthesized as surrogates of the ultrapotent DAG analogue, 5-(acetoxymethyl)-5-(hydroxymethyl) 3-[(Z)-tetradecylideneltetrahydro-2-furanone (1), a compound that showed high affinity for PKC-$\alpha$ ($K_1$=35 nM) in a competition binding assay with [$^3H$-20]phorbol-12,13-dibutyrate (PDBU). In an attempt to overcome the problem of generating geometrical E- and Z- isomers, as encountered with 1, the double bond was moved to an endocyclic location as in 3, or an additional alkyl chain was appended to C3 to give the corresponding 3,3-dialkyl saturated lactones (4 and 5). The lactone was constructed from glycidyl-4-methoxyphenyl ether in 5 steps. The target compounds showed reduced binding affinities for PKC-.alpha. with $K_{i}$ values of 192 nM (3), 4,829 nM (4), and 2,812 nM (5), respectively. These results indicate that constrained DAG analogues having a tetrahydro-2-furanone template are effectively discriminated by PKC-(X in terms of the direction of the long alkyl chain connected to the 3-position.n.

• Bulletin of the Korean Chemical Society
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• v.18 no.9
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• pp.939-945
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• 1997

Several types of 4-substituted-quinoline-2-carboxylic acid derivatives possessing different substituents at C4-position such as sulfonyl, phosphonyl, carbonyl groups, or a flexible alkyl chain have been synthesized and evaluated for their in vitro antagonistic activity at the glycine site on the N-methyl-D-aspartate (NMDA) receptor. Of them, 5,7-dichloro-4-(tolylsulfonylamino)-quinoline-2-carboxylic acid 9 was found to have the best in vitro binding affinity with IC50 of 0.57 μM. On the other hand, in compounds 21 and 22 the introduction of flexible alkyl chains on C4 of the quinoline mother nuclei caused a significant decrease of the in vitro binding affinity. In addition, replacement of polar carboxylic acid group on C2 by neutral bioisosteres in compounds 23a-d also seems to be disadvantageous to in vitro activity. In the structure-activity relationship (SAR) study of the 4-substituted quinoline-2-carboxylic acid acid derivatives, it was realized that the substitution pattern on C4 significantly influences on the binding affinity for the glycine site of NMDA receptor and the binding affinity might be increased by the introduction of a suitable electron rich substituent at C4 which has the ability of H-bonding donor.

• Archives of Pharmacal Research
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• v.20 no.1
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• pp.53-57
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• 1997

For the purpose of defining the effects of the N-substituted alkyl groups on the anticonvulsant activities of N-Cbz-.alpha.-aminosuccinimides, various (R)- and (S)-N-alkyl substituted N-Cbz-.alpha.-aminosuccinimides (1 and 2) were prepared from the corresponding (R)- and (S)-N-Cbz-aspartic acid by using known reaction and were evaluated the anticonvulsant activies in the MES and PTZ tests, including their neurotoxicities. The most active compound in the MES test was (R)N-Cbz-.alpha.-amino-N-methylsuccinimide (1b) $(ED_{50}=52.5 mg/kg, Pl=3.2)$. And in case of the PTZ test, (R)-N-Cbz-.alpha.-amino-N-ethylsuccinimide (1c) was the most active compound $(ED_{50}/=32.5mg/kg, Pl=3.1)$. The order of anticonvulsant activities of these compounds against the MES test, as judged from the ED_50values for the R series (1), was N-methyl > N-isobutyl > non-substituted > N-ethyl, N-allyl > N-benzyl compound; for the S series (2) N-methyl > N-altyl > non-substituted > N-isobutyl > N-ethyl > N-benzyl compound. The anticonvulsant activities in the PTZ tests of these compounds exhibited somewhat different pattern ; for the R series (1) Nethyl > N-methyl > N-isobutyl> non-substituted > N-allyl > N-benzyl compound in order of decreasing activity; for S series (2) N-ethyl > N-allyl, non-substituted > N-isobutyl > N-methyl > N-benzyl compound in order of decreasing activity.

• Bulletin of the Korean Chemical Society
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• v.32 no.7
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• pp.2212-2216
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• 2011

An ionic liquid-based ultrasonic-assisted extraction method has been successfully applied to the effective extraction of phenolic compounds from Laminaria japonica Aresch. Three kinds of 1-alkyl-3-methyl-imidazolium with different cations and anions were evaluated for extraction efficiency. The results showed that both the characteristics of anions and cations have remarkable effects on the extraction efficiency. In addition, the ionic liquid-based ultrasonic-assisted extraction procedure was also optimized on some extraction parameters, such as ultrasonic power, extraction time and solid-liquid ratio. Compared with the conventional solvent, the optimum approach gained the highest extraction efficiency within the shortest extraction time. Average recoveries of phenolic compounds were from 75.5% to 88.3% at three concentration levels.

• Bulletin of the Korean Chemical Society
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• v.23 no.6
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• pp.856-861
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• 2002

The general reducing charagteristics of a newly synthesized reducing agent, lithium(2.3-dimethyl-2-butyl)-${\iota}$-butoxyborohydride (Li $Thx'BuOB_2$, 1), in tetrahydrofuran (THF) toward selected organic compounds containing representative fundtional groups under practical has been examined. The reagent revealed an interesting and unique reducing characteristics. Especially, the stereoselectivity in the reduction of cyclic ketones was extraordinary. Thus, the introduction of bulky alkyl and alkoxy groups into the parent borohydride affonds a high stereoselectivity. In general, the reducing power of the reagent is somewhere between the dialiylborohydride and the parent borohydride. This permits the reagent to be a reagent of choice for selecitive reduction of organic compounds with an improved selectivity.

• Transactions on Electrical and Electronic Materials
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• v.13 no.1
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• pp.2-5
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• 2012

We have designed, synthesized, and evaluated the physical properties of some high birefringence (${\Delta}n$) isothiocyanato biphenyl-bistolane liquid crystals. These compounds exhibit ${\Delta}n^-$ 0.4-0.7 at room temperature and wavelength $\lambda$=633 nm. Laterally substituted short alkyl chains and fluorine atom eliminate smectic phase and lower the melting temperature. The moderate melting temperature and very high clearing temperature make those compounds attractive for eutectic mixture formulation. Several mixtures based on those compounds were formulated and its physical properties evaluated.

• Applied Chemistry for Engineering
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• v.9 no.4
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• pp.548-553
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• 1998

The N-unsaturated alkylcarbazole derivatives were synthesized by the nucleophilic unimolucular substitution reaction ($S_N1$) of carbazole with unsaturated alkyl chloride. These reactions between carbazole and unsaturated alkyl chloride were conducted in dimethyl sulfoxide (DMSO) containing alkali (NaOH or KOH) at room temperature for 4 hrs under nitrogen atmosphere. The mole ratios of carbazole, alkali and unsaturated alkyl chloride were 1:6:1, respectively. All of the compounds of starting materials and reaction products were characterized by CHN analysis, $^1H$-NMR and FR-IR spectroscopy.

• Journal of the Korean Wood Science and Technology
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• v.12 no.2
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• pp.27-34
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• 1984

In order to investigate the acidic chlorinated compounds in pulp bleaching spent liquor, the lignin model compounds, coniferyl alcohol(mp $74^{\circ}C$), ${\omega}$-(2-methoxyphenoxy)-acetoguaiacone(mp $93^{\circ}C$) and dehydrodiisoeugenol(mp $133^{\circ}C$), were synthesized and chlorinated by chlorine in glacial acetic acid. From the chlorinated products, the following chlorine-containing aromatic compounds were identified by TLC. In coniferyl alcohol the chlorine-substituted compounds at 4-, 5-and 4,5-position of aromatic nucleus were identified and in ${\beta}$-0-4 type the compounds substituted chlorine for alkyl group and/or hydrogen at land 1,4-position of aromatic nucleus expected to be formed by electrophilic displacement from ${\omega}$-(2-methoxyphenoxy)-acetoguaiacone were not identified but the chlorine-substituted compounds at 4-, 5-, 6- and 5,6-position of aromatic nucleus were identified.

• Journal of the Korean Society of Tobacco Science
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• v.10 no.2
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• pp.123-130
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• 1988

The volitile compounds Produced from the Maillard reaction of D-glucose and DL-alanine or DL-$\alpha$-aminobutyric acid using water or propylene glycol as a reaction amdeum were analysed by gas chromatofiraphy and mass spectrometry. From two kinds of reaction products in water 18 compounds were identified. The major compounds in a reaction product of glucose with alanine were 5-hydroxy methyl-2-furfural, 2-acetyl pyrrole and 2-formyl-5-methyl pyrrole, and those in a reaction product of glucose with $\alpha$-aminobutyric acid were 2-ethyl crotonaldehyde and 2-methyl-3, 5-dihydroxy-4H-pyran-4-one including the above 3 compounds. From two kinds of reaction products in propylene glycol solution, 35 compounds were identified. The major compounds in a reaction product of glucose with alanine were alkyl pyraainef, 2-methyl furfuryl alcohol and 2-acetyl pyrrole, and those in a reaction product of glucose with $\alpha$-aminobutyric acid were propionaldehyde PGA, 2-ehtyl crotonaldehyde, 2-acetyl pyrrole and 2-acetyl-5-ethyl furan.