• Bulletin of the Korean Chemical Society
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• v.27 no.6
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• pp.933-935
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• 2006

• Bulletin of the Korean Chemical Society
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• v.25 no.5
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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.

• Journal of the Korean Chemical Society
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• v.48 no.4
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• pp.385-393
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• 2004

2-Ethoxycarbonyl-3-methylquinoxaline 1,4-dioxide (8) was synthesized from benzofuroxan and ethyl acetoacetate. The reaction of compound 8 with hydrazine hydrate or selenium dioxide gave 2-hydrazinocarbonyl-3-methylquinoxaline 1,4-dioxide (9) or 2-ethoxycarbonyl-3-formylquinoxaline 1,4-dioxide (10), respectively. The reaction of compound 9 with alkanoyl chlorides, benzoyl chlorides, heteroacyl chlorides, and benzenesulfonyl chlorides afforded 3-methyl-2-(substituted hydrazinocarbonyl)quinoxaline 1,4-dioxides (11-14), respectively. The reaction of compound 9 with sodium azide gave 2-azidocarbonyl-3-methylquinoxaline 1,4-dioxide (15), and then its refluxing in dioxane/alcohols resulted in the Curtius rearrangement to give N-(3-methyl-1,4-dioxoquinoxalin-2-yl)-alkyl carbamates (16). The reaction of compound 15 with substituted anilines afforded 2-(3-substituted phenylureido)-3-methylquinoxaline 1,4-dioxides (17). The reaction of compound 10 with benzoic hydrazide or substituted anilines provided quinoxaline 1,4-di-oxides (18, 19), respectively. The herbicidal and fungicidal activities of the synthesized compounds were investigated.

• Bulletin of the Korean Chemical Society
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• v.31 no.3
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• pp.746-748
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• 2010

• YAKHAK HOEJI
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• v.36 no.5
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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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• v.42 no.12
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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.