• 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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• 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.

• 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.

• 공업화학
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• 제5권3호
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• pp.413-418
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• 1994

(2-(2, 6-디클로로페닐)아미노)페닐 아세트산나트륨의 합성단계를 줄이고 각 단계별 합성수율을 향상시켰다. 합성은 4단계로 하였으며 출발물질은 2,6-디클로로아닐린과 모노브로모벤젠을 사용하였다. 첫단계인 Ullmann반응은 구리촉매를 3회 분할 첨가하여 80%의 수율로 진행시켰고, 아실화와 프리델-크라프트 반응도 효율적으로 단순화하였다. 최종 반응생성물인 디클로페낙은 클라이젠 용액을 사용하여 제3단계에서 얻은 1-(2, 6-디클로로페닐)-2-인돌리논을 가수분해함으로써 97%의 수율로 얻었다.