• Bulletin of the Korean Chemical Society
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• v.30 no.2
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• pp.459-463
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• 2009

Furoxanaldehydes possessing phenyl or alkenyl groups at the 3- or 4-position of the furoxan ring were designed for alkyne formation on a solid surface. Furoxans 2 and 3 were prepared from the corresponding alkenes 2a and 3a by the reaction with NaN$O_2$ in acetic acid. Furoxan 4, in which the furoxan ring is conjugated with a double bond, was prepared from bis(bromomethyl)benzene 4a in 5 steps using the Wittig reaction of aldehyde 1 as the key step. The electron beam-mediated fragmentation of furoxanaldehydes 1-4 in a mass spectrometer was exploited by focusing on alkyne formation on the solid surface. The fragmentation of furoxan 3 possessing diaryl groups afforded diarylacetylene at high efficiency, suggesting that the aryl group conjugated with the furoxan ring could facilitate alkyne formation with the evolution of NO.

• Bulletin of the Korean Chemical Society
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• v.19 no.5
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• pp.506-507
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• 1998

• Bulletin of the Korean Chemical Society
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• v.33 no.8
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• pp.2765-2768
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• 2012

• Bulletin of the Korean Chemical Society
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• v.32 no.10
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• pp.3802-3804
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• 2011

• Proceedings of the Korean Vacuum Society Conference
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• 2006.08a
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• pp.102-102
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• 2006

• Asian Pacific Journal of Cancer Prevention
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• v.15 no.15
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• pp.6343-6347
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• 2014

Multi-target drug design, in which drugs are designed as single molecules to simultaneously modulate multiple physiological targets, is an important strategy in the field of drug discovery. QT-011, a tamibarotene-furoxan derivative, was here prepared and proposed to exert synergistic effects on antileukemia by releasing nitric oxide and tamibarotene. Compared with tamibarotene itself, QT-011 displayed stronger antiproliferative effects on U937 and HL-60 cells and was more effective evaluated in a nude mice U937 xenograft model in vivo. In addition, QT-011 could release nitric oxide which might contribute to the antiproliferative activity. Autodocking assays showed that QT-011 fits well with the hydrophobic pocket of retinoic acid receptors. Taken together, these results suggest that QT-011 might be a highly effective derivative of tamibarotene and a potential candidate compound as antileukemia agent.

• Bulletin of the Korean Chemical Society
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• v.31 no.12
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• pp.3583-3587
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• 2010

Furoxanthiols PFT and BPFT possessing thiomethyl or thiobenzyl groups in the furoxan ring were designed and synthesized as potential light-sensitive alkyne precursors on a gold surface. The synthesis of thiofuroxans PFT and BPFT was performed from the corresponding halofuroxans 1b and 2c, respectively, by the substitution with potassium thioacetate in ethyl acetate/ethanol or DMF, followed by basic hydrolysis as the key reactions. Electron-beammediated fragmentation of furoxans 1c and 2d in a mass spectrometer afforded the corresponding aryl alkyne fragments, with the evolution of NO in high preference. In the cases of thiofuroxans PFT and BPFT, carbon-sulfur bond cleavage was observed as a representative fragmentation, producing M-SH and M-SAc peaks, which competed with the release of NO. In the fragmentation of mono-aryl furoxan 1c, the release of molecule of NO was predominately observed to produce an M-NO fragment as a base peak by the formation of trimembered thiiranium or azirine intermediate.

• Bulletin of the Korean Chemical Society
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• v.31 no.5
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• pp.1400-1402
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• 2010

• Bulletin of the Korean Chemical Society
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• v.34 no.6
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• pp.1864-1866
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• 2013

• Journal of the Korean Chemical Society
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• v.51 no.2
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• pp.160-164
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• 2007

Aminofuroxan derivatives 3 and 4 were prepared by the reaction of chlorofuroxan 2 with butyl and benzyl amines, respectively. E-beam mediated fragmentation of aminofuroxans 3, 4 in mass spectrometer was analyzed in a view of the corresponding alkyne formation.