• Bulletin of the Korean Chemical Society
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• 제30권10호
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• pp.2381-2386
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• 2009

The tetrakis(thio)-substituted-1,4-benzoquinone products 4a-e, 6, 7, and the mono(alkoxy)-tris(thio)-substituted-1,4- benzoquinone products 5a-e and 8a-e were synthesized from the reactions of p-chloranil with some thiols and mixture of two different thiol compounds in alcohol in the presence of $Na_2CO_3$ at room temperature. The structures of the novel S,S,S,S- and S,S,S,O- substituted products, which were obtained by the reactions of p-chloranil as a starting compound with n-propanethiol, n-pentanethiol, n-decanethiol, n-dodecanethiol, 2-methyl-2-propanethiol, and mixture of n-decanethiol and n-cyclohexanethiol as S-nucleophiles, were characterized by spectroscopic methods.

• Preventive Nutrition and Food Science
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• 제4권2호
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• pp.122-124
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• 1999

Induction of NAD(P)H : (quinone-acceptor) oxidoreductase (QR) which obligatory two electron reduction of quinones and prevents their participation in oxidative cycling and thereby the depletion of intracellular glutathione, has been used as a marker for chemopreventive agents. We postulated that vitamin E, an antioxidant, which induces QR as the gene of QR was reported to contain antioxidant reponsive element in the 5'-flanking region. Vitamin E resulted in significant induction of QR in both hepalclc7 cells and mouse tissues. QR induction was observed; to be maximal at 25uM vitamin E for hepalclc7 cells while it was maximal in the level of 2.5∼5 μmoles vitamin E/㎏ BW for mouse tissues. Thus the cancer-preventive effect of vitamin E may be exerted by it induction of intracellular detoxifying enzymes.

• 한국식품영양과학회지
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• 제24권3호
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• pp.459-465
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• 1995

The ether extract of Salviae miltiorrhizae Radix(SMR) was fractioned to give five subfractions, so that two subfractions of them were recrystallized to yield each pure diterpene quinone pigment. On the basis of spectral evidence, these two compounds were identified as tanshinone II and crytotanshinone. Cryptotanshinone exhibited both of a potent platelet anti-aggregating activity in vitro and a potent antimicrobial activity. GC-MS analysis of the other extract showed that tanshinone II was contained in the largest proportion of all the diterpene quinones. In addition, GC-MS analysis gave other valuable analytical informations.

• 대한화학회지
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• 제47권1호
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• pp.47-58
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• 2003

알킬화제로 작용할 수 있는 naphthoquinones인 fibrostatin이 Streptomyces catanulae subsp. griseospora 배양액으로부터 추출되었다. 이들 quinone 화합물의 합성은 이 화합물들의 생물학적 반응성 연구에 매우 중요하다. 본 논문에서는 효과적으로 치환체들의 위치를 조절할 수 있는 방법인 Hooker oxidation을 이용하여 fibrostatin B를 합성하였다.

• Bulletin of the Korean Chemical Society
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• 제12권6호
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• pp.612-617
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• 1991

The approximate rates and stoichiometry of the reaction of excess 1,3,2-biphenyldioxaborepin [2,2'-biphenoxyborane (BPB)] with selected organic compounds containing representative functional groups under the standardized conditions (tetrahydrofuran, hydride to compound being 4 : 1, room temperature) was examined in order to define the characteristics of the reagent for selective reductions and compare its reducing power with those of other substituted boranes. The results indicate that BPB is unique and the reducing power is much stronger than that of other dialkoxyboranes, such as catecholborane and di-s-butoxyborane. BPB reduces aldehydes, ketones, quinones, lactones, tertiary amides, and sulfoxides readily. Carboxylic acids, anhydrides, esters, and nitriles are also reduced slowly. However, the reactions of acid chlorides, epoxides, primary amides, nitro compounds, and disulfides with this reagent proceed only sluggishly.

• Bulletin of the Korean Chemical Society
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• 제12권6호
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• pp.644-649
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• 1991

The approximate rates and stoichiometry of the reaction of excess lithium tris(dibutylamino)aluminum hydride (LT-DBA) with selected organic compounds containing representative functional groups under standardized conditions (tetrahydrofuran, $0^{\circ}C$) were studied in order to characterize the reducing characteristics of the reagent for selective reductions. The reducing ability of LTDBA was also compared with those of the parent lithium aluminum hydride and the alkoxy derivatives. The reagent appears to be much milder than the parent reagent, but stronger than lithium tri-t-butoxyaluminohydride in reducing strength. LTDBA shows a unique reducing characteristics. Thus, the reagent reduces aldehydes, ketones, esters, acid chlorides, epoxides, and amides readily. In addition to that, ${\alpha},{\beta}$-unsaturated aldehyde is reduced to ${\alpha},{\beta}$-unsaturated alcohol. Quinones are reduced to the corresponding diols without evolution of hydrogen. Tertiary amides and aromatic nitriles are converted to aldehydes with a limiting amount of LTDBA. Finally, disulfides and sulfoxides are readily reduced to thiols and sulfides, respectively, without hydrogen evolution.

• 대한약학회:학술대회논문집
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• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-2
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• pp.182.2-182.2
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• 2003

The abnormal proliferation and migration of vascular smooth muscle cell (SMC) play an important role in the pathology of coronary artery atherosclerosis and restenosis. Platelet-derived growth factor (PDGF) is one of the most potent promoters of the proliferation and migration of the SMC. The heterocyclic quinones represent an important class of biologically active molecules. However, the inhibitory activity of quinone classes on the proliferation of the SMC has not been reported. (omitted)

• 대한환경공학회지
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• 제33권6호
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• pp.396-404
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• 2011

본 연구에서는 PAHs 오염토양의 화학적 생물학적 처리과정에서 반응부산물로 흔히 발견되는 PAH-퀴논화합물을 대상으로 수용액 상에서의 망간산화물에 의한 산화-변환 제거 특성(제거율, 반응속도)을 조사하였다. 반응시간 경과에 따른 상등액의 HPLC 분석결과로부터 p-퀴논화합물인 Acenaphthenequinone (APQ)는 망간산화물 자체에 의한 산화-결합 반응을 통해 제거되며, o-퀴논화합물인 Anthraquinone (AQ)와 1,4-Naphthoquinone (1,4-NPQ)는 반응매개체(Catechol) 존재 하에서의 교차-결합반응을 통해 효과적으로 제거 가능함을 확인하였다. 망간산화물에 의한 PAH-퀴논화합물의 제거는 유사-일차 반응 속도식을 따랐으며, 본 실험조건(1,4-NPQ = 11.5 mg/L, CAT = 50 mg/L, $MnO_2$ = 1.0 g/L, pH 5, 반응시간 = 6~96 hr)에서의 1,4-NPQ의 교차-결합 반응속도상수(k, $hr^{-1}$)는 0.0426으로 APQ의 산화-결합 반응속도 상수(0.173)에 비교해 약 4배 정도의 차이를 보였다. 동일조건에서의 망간산화물 주입량별 속도상수를 망간산화물의 비표면적으로 표준화하여 얻은 1,4-NPQ의 교차-결합 반응에 대한 비표면적표준화속도상수($K_{surf}$)는 $8.5{\times}10^{-4}L/m^2{\cdot}hr$이었다. 망간산화물 주입량별 제거특성과 반응 속도상수의 비교 해석 결과로부터 1,4-NPQ의 교차-결합 반응은 반응시간 경과에 따라 서로 다른 반응기작을 거침을 확인하였으며, 이를 기존 문헌결과와 함께 해석하였다.

• 한국환경농학회지
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• 제35권3호
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• pp.216-222
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• 2016

Polychlorinated biphenyl은 잔류성 환경 오염물질로서, 다양한 생리 독성 때문에 인축에 대한 세부적 연구가 수행된 바 있다. 한편 포유동물을 대상으로 진행된 연구에서 hydroxy PCBs, PCB quinones, 및 methylsulfonyl PCBs 등의 대사물이 발견되었으며, 이들은 모화합물과는 상이한 독성을 나타낸다고 보고되었다. 그러나 이와 같은 동물에 대한 연구와 비교하여, 식물 및 토양 미생물에 대한 영향, 독성 등에 대한 연구는 매우 제한적이다. 일반적으로 식물의 경우, 농약 등과 같은 외래 물질 또는 자외선, 병원균 등의 외래 스트레스원의 작용을 받게되면, 특이 생물활성을 지닌 파이토알렉신 등의 이차 대사산물을 생합성하는 것이 알려져 있다. 본 연구에서는 수 종의 PCB 및 hydroxy PCB, phenol류 등을 화학적으로 합성하고, 이들의 처리에 따른 당근 중, 파이토알렉신인 6-메톡시멜레인 생합성에 미치는 영향을 검토하였다. 증류수를 처리한 대조구의 경우, 파이토알렉신의 농도는 처리 후 2일에 최대치까지 증가하였으며, 이후 지속적으로 감소하였다. 한편 2-hydroxy/4-hydroxybiphenyl의 경우, 처리 후 3일까지 증대한 반면, 비교적 지용성이 높은 PCB-126 및 3,5-dichloro-2-hydroxybiphenyl 처리구에서는 처리 1일 후, 최대치를 나타내어 화합물의 구조 또는 지용성 등에 따라 다른 유도효과를 나타내었다. 이상의 결과에 따라, 환경 오염물질의 성상에 따라, 토양 중, 재배 농작물의 생리 활성 2차 대사물질의 생합성이 다양하게 변화됨을 알 수 있었다.

• 대한화학회지
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• 제64권1호
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• pp.7-18
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• 2020

An efficient and facile procedure has been developed for the synthesis of novel bichalcone derivatives (4a, 4b). The key step contains the solvent-free aldol synthesis of bichalcones based on quinones. Bichalcones (4a, 4b) were used as precursors for the synthesis of some interesting heterocyclic compounds like, diazepines (5a, 5b), pyrazolo-pyrimidines (7a, 7b), and pyrazoline derivatives (8a, 8b). Moreover, new thioxopyrimidine derivatives (9a, 9b) were furnished and used as a functionalizing agent to produce the triazole-pyrimidines (11, 12) and the carbonitrile derivative (14). All the synthesized compounds were fully characterized using physical and spectral data like, FT-IR, ¹H NMR, ¹³C NMR, and MS. Bichalcones (4a, 4b) and diazepines (5a, 5b) were screened for their anticonvulsant activity, where compounds (4a, 5a, and 5b) revealed potent anticonvulsant activity compared to diazepam. On the other hand, some of the prepared compounds were screened for their antiproliferative activity and they showed significant cytotoxic effects on most of the cancer cell lines with regard to broad spectrum antitumor activity.