• 한국응용약물학회:학술대회논문집
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• 한국응용약물학회 1994년도 춘계학술대회 and 제3회 신약개발 연구발표회
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• pp.220-220
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• 1994

출발물질로 L-tyrosine을 사용하여 요오드화, 에스테르화, N-BOC 및 0-Bn보호기화 및 N 탈보호기화를 행하여 5단계에 걸쳐 41%의 수율로 methyl 0-Bn-3-iodotyrosinate를 합성하였다. 또한 Ullmann coupling의 반응성 향상을 위해 5위치에 nilro기가 도입된 methyl 0-Bn-3-iodo-5-nitrotyrosinate를 좋은 수율로 합성하였다. 이들에 N-BOC-tyrosine을 결합시켜 대응하는 dipeptide를44% 및 39%의 수율로 각각 얻었다. 일단 dipeptide에 대해 Ullmann coupling을 행하였으나 원하는 cyclic product는 얻을수 없었다. 전년도에 이어 methyl N-BOC-0-Bn-3-hydroxytyrosinate를 합성하였다. 이로 부터 4-iodobenzaldehyde에 Ullmann coupling을 행하여 원하는 페놀성 biaryl ether를 합성하고자 하였다. 또한 $\beta$-hydroxyhomoserine의 합성을 위해 출발물질로 cis-1,4-buterdiol을 사용하여 12단계의 합성반응을 행하여 좋은수율로 원하는 화합물을 합성하였다.

• Bulletin of the Korean Chemical Society
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• 제34권12호
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• pp.3915-3918
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• 2013

• 약학회지
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• 제55권6호
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• pp.441-445
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• 2011

A series of 8-(substituted)aryloxy- and 8-alkyloxy-caffenines were prepared from 8-bromocaffeine and (substituted) phenols as well as alkanols by Ullmann reaction and their inhibitory activities on topoisomerase II were evaluated. A compound, 8-(quinolin-2-yl)oxycaffeine showed the strongest inhibitory activity against topoisomerase II.

• Bulletin of the Korean Chemical Society
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• 제26권10호
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• pp.1614-1616
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• 2005

• Bulletin of the Korean Chemical Society
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• 제24권8호
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• pp.1049-1050
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• 2003

• Bulletin of the Korean Chemical Society
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• 제35권11호
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• pp.3219-3223
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• 2014

Ochnaflavone, a naturally occurring biflavonoid composed of two units of apigenin (5,7,4'-trihydroxyflavone) joined via a C-O-C linkage, was first synthesized and evaluated its inhibitory activity on $PGE_2$ production. Total synthesis was accomplished through modified Ullmann diaryl ether formation as a key step. Coupling reactions of 4'-halogenoflavones and 3'-hydroxy-5,7,4'-trimethoxyflavone were explored in diverse reaction conditions. The reaction of 4'-fluoro-5,7-dimethoxyflavone (2c) and 3'-hydroxy-5,7,4'-trimethoxyflavone (2d) in N,N-dimethylacetamide gave the coupled compound 3 in 58% yield. Synthetic ochnaflavone strongly inhibited PGE2 production ($IC_{50}=1.08{\mu}M$) from LPS-activated RAW 264.7 cells, which was due to reduced expression of COX-2. On the contrary, the inhibition mechanism of wogonin was somewhat different from that of ochnaflavone although wogonin, a natural occurring anti-inflammatory flavonoid, showed strong inhibitory activity of $PGE_2$ production ($IC_{50}=0.52{\mu}M$), and seems to be COX-2 enzyme inhibition. Our concise total synthesis of ochnaflavone enable us to provide sufficient quantities of material for advanced biological studies as well as to efficiently prepare derivatives for structure-activity relationship study.

• 한국인쇄학회지
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• 제16권3호
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• pp.133-146
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• 1998

The conversion of 1-Amino-4-(3'-Acetaminoanilino) Anthraquinone-2-Sulfonic Acid prepared by the Ullmann condensation have been investigated as a function of the reaction conditions such as catalysts, initial concentration of reactants, reaction temperature, pH, condensation agents and neutralizing agents. The experimental results showed that the Cu(I)-type catalysts had higher activity than the Cu(II)-type catalysts in this study. The conversion increased with increasing initial concentration of reactants but decreased at above critical concentration owing to agglomeration of reactants. It was also observed that the maximum conversion obtained at 7$0^{\circ}C$ and pH=7~8.

• 한국응용약물학회:학술대회논문집
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• 한국응용약물학회 1993년도 제2회 신약개발 연구발표회 초록집
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• pp.117-117
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• 1993

3. 연구결과 출발물질로 L-tyrosine을 사용하여 요오드화, 에스테르화, N-CBZ 및 0-Bn보호기화 및 N-methyl화를 행하여 5단계에 걸쳐 41%의 수율로 N-CBZ-N-methyl-0-Bn-3-iodo-tyrosine을 합성하였다. Ullmann coupling의 반응성 검토를 위해 t-bromophenylala-nine에 반응시킬 3-hydroxytyrosine 유도체를 합성하고자 L-tyrosine에 Friedel-Craft acyl화, 에스테르화, 아민의 보호기화 및 Baeyer-Villiger 반응들을 행하였다. 또한 특이한 아미노산인 $\beta$-hydroxytyrosine의 합성을 위해 출발물질로 p-hydroxybenzalde-hyde를 사용하여 6단계에 28%의 수율로 oxazolidinoe acid를 합성하였다. 이로부터 4단계 반응을 행하여 보호된 $\beta$-hydroxy-tyrosine을 52%의 수율로 합성하였다.

• 한국재료학회지
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• 제15권7호
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• pp.448-452
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• 2005

This study was based on organic electroluminescence display. Especially, TPD and $\alpha-NPD$ for the hole transport materials were synthesized by Ullmann reaction. This reaction was conducted between 3­methylphenylamine, 1-naphthylamine and 4,4'-diiodobiphenyl in toluene containing CuCl catalyst and KOH base. The structural property of reaction products were analyzed by FT-IR, $^1H-NMR$ spectroscopy, and thermal stability, reactivity and PL property were analyzed by melting point, yield and emission spectrum, respectively. The photoluminescence spectra of a pure TPD and $\alpha-NPD$ were observed at approximately 416nm and 438nm respectively. In this study, it was known that the melting point, yield, PL properties of TPD and $\alpha-NPD$ were changed by substituent group of amines.

• Journal of Industrial and Engineering Chemistry
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• 제68권
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• pp.99-108
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• 2018

An oil-tolerant and salt-resistant aqueous foam system was screened out as a possible lubricant to enable cold heavy oil transportation. The microstructures and viscoelasticity and effects of heavy oil, salt and temperature on the foam stability were investigated and new rheological and drainage models were established. The results indicate the foam with multilayered shells belongs to a special microcellular foam. The viscoelasticity could be neglected due to its low relaxation time. The drainage process can be divided into three stages. The foam with quality of 67.9% maintains great stability at high oil and salt concentrations and appropriate elevated temperature.