• Bulletin of the Korean Chemical Society
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• 제27권6호
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• pp.933-935
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• 2006

• Bulletin of the Korean Chemical Society
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• 제25권5호
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• pp.668-672
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• 2004

This paper reports the stereoselective synthesis of a novel nucleoside, 4'-methyl branched and bicyclo [3.1.0] hexane locked-nucleoside 12, using a sequential [3,3]-sigmatropic rearrangement/carbene cycloaddition reaction/Curtius reaction strategy with a high stereoselectivity.

• 대한화학회지
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• 제48권4호
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• pp.385-393
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• 2004

Benzofuroxan과 ethyl acetoacetate를 반응시켜 2-ethoxycarbonyl-3-methylquinoxaline 1,4-dioxide (8)를 합성하고, 이것을 hydrazine hydrate 또는 selenium dioxide와 반응시켜 2-hydrazinocarbonyl-3-methylquinoxaline 1,4-dioxide (9) 또는 2-ethoxycarbonyl-3-formylquinoxaline 1,4-dioxide (10)를 합성하였다. 화합물 9를 alkanoyl chloride류, benzoyl chloride류, heteroacyl chloride류 및 benzenesulfonyl chloride류와 반응시켜 3-methyl-2-(substituted hydrazinocarbonyl)quinoxaline 1,4-dioxide류 (11-14)를 합성하였다. 화합물 9를 sodium nitrite와 반응시켜 2-azidocarbonyl- 3-methylquinoxaline 1,4-dioxide (15)를 합성한 다음, 이것을 디옥산/알코올류 용매하에서 환류시켜 Curtius 자리옮김반응에 의한 N-(3-methyl-1,4-dioxoquinoxalin-2-yl)-alkyl carbamate류 (16)를 합성하였다. 그리고 화합물 15를 치환 아닐린류와 반응시켜 2-(3-substituted phenylureido)-3-methylquinoxaline 1,4-dioxide류 (17)를 합성하였다. 한편 화합물 10을 benzoic hydrazide 또는 치환 아닐린류와 반응시켜 quinoxaline 1,4-dioxide류 (18, 19)를 각각 합성하였다. 그리고 합성한 화합물들에 대한 제초력과 살균력도 조사하였다.

• Bulletin of the Korean Chemical Society
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• 제31권3호
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• pp.746-748
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• 2010

• 약학회지
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• 제36권5호
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• pp.433-439
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• 1992

For the synthesis of tuberin derivatives, N-(disubstituted styryl) carboxamides, the series of cinnamic acids were transformed through chlorides, azides to isocyanates. And then isocyanates were reduced separately by Dibal and Grignard reagent. As a result of antimicrobial susceptibility test, N-(3,4-dichlorostyryl) formamide and N-(3,4-dichlorostyrl) acetamide showed comparatively large activity against some bacteria that is, MIC was respectively 50 ppm, $6.25{\sim}50\;ppm$. MIC of other derivatives was similiar to that of tuberin, about 100.

• BMB Reports
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• 제42권12호
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• pp.806-811
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• 2009

Recently, various phenolic acid phenethyl ureas (PAPUs) have been synthesized from phenolic acids by Curtius rearrangement for the development of more effective anti-oxidants. In this study, we examined the anti-tumor activity and cellular mechanism of the synthetic compound (E)-1-(3,4-dihydroxyphenethyl)-3-styrylurea (PAPU1) using melanoma B16/F10 and M-3 cells. Results showed that PAPU1 inhibited the cell proliferation and viability, but did not induce cytotoxic effects on primary cultured fibroblasts. PAPU1 induced apoptotic cell death rather than necrosis in melanoma cells, a result clearly proven by the shift of cells into sub-$G_1$ phase of the cell cycle and by the substantial increase in cells positively stained with TUNEL or Annexin V. Collectively, this study revealed that PAPU1 induced apoptosis in a caspase-dependent manner, suggesting a potential role as a cancer chemopreventive agent for melanoma cells.