• Archives of Pharmacal Research
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• 제22권4호
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• pp.384-390
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• 1999

Thirty-four glutathione conjugates of 5,8-dimethoxy-1,4-naphthoquinones (DMNQ) were synthesized and their structure was determined. The yield of GSH conjugate was dependent on size of alkyl group; the longer the size of alkyl group was, the lower was the yield. It was also found that the length of alkyl side chain influenced the chemical shift of quinonoid protons; the quinonoid protons of 2-glutathionyl DMNQ derivatives with R=H to propyl, 6.51-6.59 ppm vs. other ones with R=butyl to heptyl, 6.64-6.68 ppm. this was explained to be due to a folding effect of longer alkyl group. Glutathione (GSH) reacted with DMNQ derivative first to form a 1,4-adduct (2- or 3-glutathionyl-1,4-dihydroxy-5,8-dimethoxynaphthalenes) and then the adduct was autooxidized to 2- or 3-glutathionyl-DMNQ derivatives. Moreover, GSH reduced DMNQ derivatives to their hydrogenated products. It was suggested that such an organic reaction might play an important role for a study of metabolism or toxicity of DMNQ derivative sin the living cells.

• Macromolecular Research
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• 제16권1호
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• pp.36-44
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• 2008

A series of polysiloxanes containing alkylsulfonyl side groups were synthesized using a polymer analogous reaction beginning from poly(methylhydrosiloxane) and the corresponding olefins. These polymers showed a mesomorphic behavior with smectic liquid crystalline phases. The chemical and physical properties of these polymers were examined using nuclear magnetic resonance spectroscopy, gel permeation chromatography, differential scanning calorimetry, optical polarizing microscopy, and X-ray diffraction.

• 대한화학회지
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• 제36권2호
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• pp.293-300
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• 1992

신규 cephalosporin계 항생제로서, 7-[(Z)-2-(2-aminothiazol-4-yl)-2-oxyiminoacetamido]-3-(4,6-diamino-1-alkyl-1,3,5-triazinium-2-yl)thiomethyl-3-cephem-4-carboxylate의 유도체들을 합성하였다. 7-위치의 side chain에 있는 oxyimino 부위를 변화시켜서, 구조 변화에 따른 항균 활성의 변화를 측정하였다. 그 결과, 3-위치에서 4,6-diamino-1-methyl-1,3,5-triazinium-2-yl group을 가지며, 또한 7-$\alpha$-methoxyimino기를 가진, C-1유도체가 가장 강력하고도 광범위한 항균활성을 그람 양성과 그람 음성 bacteria에 대하여 나타내었다.

• Bulletin of the Korean Chemical Society
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• 제21권11호
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• pp.1119-1124
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• 2000

$\beta-Cyclodextrin$ derivatives connected with diaza-18-crown-6 through flexible bridges (R) at the secondary face 1a-c (1a: R = $-(CH_2)4-;$ 1b: R = $-CH_2CH_2OCH_2CH2-;$ 1c: R = $-(CH_2)8-)$ have been prepared. The associa tion constants of 1 with (2-naphthoxy)alkylammonium ions (2a: alkyl = butyl; 2b: alkyl = octyl) were determined by induced circular dichroism (ICD) spectroscopy and it was found that the derivatization of $\beta-CD$ with the diazacrown resulted in enhanced binding with 2, compared to the native $\beta-CD.$ ICD Characteristics of the host-guest complexes indicate that a part of the alkylammonium moiety of 2 is protruded from the secondary side of the $\beta-CD$ cavity, and the guest molecules 2a and 2b move to the secondary and primary side, respectively, to make the binding of the ammonium group with the diaza-18-crown-6 moiety more feasible. The energy accompanied by the relocation of the guest molecules inside $\beta-CD$ moiety is compensated by the interaction energy between the ammonium ion and diazacrown ether.

• 공업화학
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• 제9권1호
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• pp.1-5
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• 1998

올리고머형 음이온성 계면활성제로서 소수성인 측쇄알킬기의 탄소수와 중합도가 다른 말레인산디에틸에스테르계(CmD-Na계) 또는 무수말레인산계(CmM-Na계)와 탄소수가 $C_4{\sim}C_{16}$인 알킬비닐에테르 공중합물을 분산제로 사용하여 분산이 잘 안되는 ${\alpha}-$나 ${\beta}-$형 copper phthalocyanine과 카본블랙의 미립자에 대하여 수용액중에서의 분산성을 비교검토 하였다. 그 결과 CmD-Na계의 측쇄알킬기의 탄소수가 $C_4{\sim}C_{10}$인 경우에는 0.01~0.1% 농도범위에서 우수한 분산효과를 나타내었고, 특히 측쇄알킬기가 안료입자 표면으로의 배향흡착에 중요한 역할을 하며, 중합도가 낮은 것이 효과적으로 나타났다. 그러나 카본블랙인 경우에는 이와 무관한 결과를 나타내었다.

• Macromolecular Research
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• 제15권2호
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• pp.185-190
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• 2007

Poly(norbornene dimethyl dicarboxylate)s, (PNDMD)s, were prepared by addition polymerization with palladium(II) catalyst from pure exo-monomers, and their structure and properties were compared with those of poly(norbornene dicarboxylic acid dialkyl ester)s, (PNDADA)s. Both polymer series exhibited good solubility in general organic solvents and excellent thermal stability up to $330^{\circ}C$. Wide-angle X-ray scattering (WAXS) study indicated the presence of nano-scale layer-like order in amorphous PNDADAs, while PNDMDs showed random amorphous structure. The glass transition temperatures and dielectric constants of solid polymers were found to decrease as the alkyl side-chain length increases for both polymer series. However, PNDMDs showed lower glass transition temperatures and higher dielectric constants, as compared with those of PNDADAs containing the same alkyl substituents. This difference, caused by the higher side-group mobility of PNDMDs, may be closely related to the nano-scale order in amorphous PNDADAs and its absence in PNDMDs.

• 한국정보디스플레이학회:학술대회논문집
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• 한국정보디스플레이학회 2007년도 7th International Meeting on Information Display 제7권1호
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• pp.890-892
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• 2007

We report the syntheses and characterizations of a novel TTF derivative. To extend the mesogenic core, alkoxy naphthalenic group and short alkyl chains were introduced on either side of TTF unit, which results in asymmetric planar structure. TTF molecule is expected to show many interesting properties.

• 약학회지
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• 제44권2호
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• pp.141-148
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• 2000

A new synthetic method of 6-(1-oxyalkyl)-5,8-dimethoxy-1,4-naphthoquinones was developed, 2-formyl-1,4,5,8-tetramethoxynaphthalene was oxidized to form 6-formyl-5,8-dimethoxy-1,4-naphthoquinone(DMNQ). This was selectively reduced and benzylated to produce 6-formyl-5,8-dimethoxy-1,4-dibenzyloxynaphthalene, to which various alkylmagnesium halide were added, followed by debenzylation and oxidation in sequence, yielding 6-(1-hydroxyalkyl)-DMNQ derivatives. 6-(1-hydroxyalkyl)-5,8-diethoxy-1,4-naphthalene (DENQ) derivatives were synthesized by similar procedure. 1'-OH of the naphthoquinone derivatives was acylated with various alkanoic acids to give 6-(1-acyloxyalkyl)-DMNQ or DENQ derivatives. TOPO-I inhibitory activity and cytotoxicity of DENQs were less potent than that of DMNQs. Among the DMNQ and DENQ analogues, the ones with alkyl group being heptyl were most potent in TOPO-I inhibition $IC_{50}$/; 30.1, 36.4 $\mu$M). DUNQ derivatives with a longer side chain exhibited a weaker cytotoxicity. A correlation between size of the alkyl side chain and cytotoxicity was not observed for DENQ derivatives. Acylation of 1'-hydroxyl group, in general, decreased both TOPO-I inhibitory activity and cytotoxicity T/C (%) values of the DENQ derivatives on S-180 intraperitoneal tumor were larger than those of DMNQ derivatives. Among the compounds synthesized,6-(1-hydroxyheptyl)-DENQ and 6-(1-hex-anoyloxyoctyl)-DMNQ showed the highest T/C values of 183% and 182%, respectively.

• 공업화학
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• 제29권4호
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• pp.405-412
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• 2018

알칸디올로부터 유래된 주사슬의 탄소수가 6, 9, 11인 bis[3-(dialkyloxylphosphorothionyl)thio-2-methylpropanyloxy]alkane (BAPA)를 합성하였으며, 이를 zinc dialkyl dithiophosphates (ZDDP)와 비교하여 마모억제성능을 살펴보았다. 탄소 주사슬의 길이에 따른 BAPA의 내마모성능을 확인하기 위하여 4-ball 시험을 하였다. 기유무게의 1% 농도로 첨가제를 넣고 WSD (wear scar diameter)를 측정하였고, 각 0.472, 0.459, 0.480 mm로 나타났다. 또한 BAPA 화합물 중 bis[methacryloyloxy]nonane (BMOO9)의 곁사슬인 dialkyl dithiophosphoric acid (DDP)의 탄소수를 4, 8, 12로 변화시켜 합성하여, 4-ball 시험을 하였다. 그 결과로 WSD의 값은 각각 0.537, 0.459, 0.531 mm로 측정되었다. 곁사슬이 짧으면 필름이 얇게 형성되고, 길면 필름형성을 방해하여 탄소수가 8개일 때의 값이 제일 좋게 나타났다. ZDDP의 경우 동일한 조건에서 WSD의 값이 0.563 mm로 측정되었고, 합성한 BAPA의 화합물이 마모억제용 첨가제로 더 우수한 성능을 갖는다는 것을 확인하였다.

• Archives of Pharmacal Research
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• 제21권6호
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• pp.738-743
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• 1998

Thirty six 5,8-dimethoxy-1,4-naphthoquinone derivatives, which bear unsaturated alkyl side chain with ester bond, were synthesized and tested cytotoxic activity on L1210 cells a nd antitumor activity against ICR mice bearing S-180 cells. It could be recognized that the cytotoxicities of naphthoquinones with R1, being methyl and propyl (IV1~24) were not enhanced by replacing the alkanoyls with alkenoyls. In contrast, the introduction of the alkenoyl moieties on the compounds with $R_1$=hexyl (IV25~36) resulted in the enhancement of their cytotoxicities. Replacement of alkanoyl group with an alkenoyl group generally increased the T/C value of the mice bearing S-180 cells.