Concise syntheses of N-aryl-5,6,7-trimethoxyindoles as antimitotic and vascular disrupting agents: Application of the copper-mediated Ullmann-type arylation

Hsueh Yun Lee; Jang Yang Chang; Ling Yin Chang; Wen Yang Lai; Mei Jung Lai; Kuang Hsing Shih; Ching Chuan Kuo; Chi Yen Chang; Jing Ping Liou

doi:10.1039/c0ob01038c

Concise syntheses of N-aryl-5,6,7-trimethoxyindoles as antimitotic and vascular disrupting agents: Application of the copper-mediated Ullmann-type arylation

Hsueh Yun Lee, Jang Yang Chang, Ling Yin Chang, Wen Yang Lai, Mei Jung Lai, Kuang Hsing Shih, Ching Chuan Kuo, Chi Yen Chang, Jing Ping Liou

Research output: Contribution to journal › Article › peer-review

22 Citations (Scopus)

Abstract

In an attempt to mimic the 3,4,5-trimethoxyphenyl-Z-stilbene moiety of combretastatin A-4, a series of N-aryl-5,6,7-trimethoxyindoles were synthesized via copper-catalyzed Ullmann-type N-arylation through the corresponding 5,6,7-trimethoxyindole and aryl halides. These synthesized compounds demonstrated potent antiproliferative activity providing a novel skeleton for potent tubulin polymerization inhibitors.

Original language	English
Pages (from-to)	3154-3157
Number of pages	4
Journal	Organic and Biomolecular Chemistry
Volume	9
Issue number	9
DOIs	https://doi.org/10.1039/c0ob01038c
Publication status	Published - 2011 May 7

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Lee, H. Y., Chang, J. Y., Chang, L. Y., Lai, W. Y., Lai, M. J., Shih, K. H., Kuo, C. C., Chang, C. Y., & Liou, J. P. (2011). Concise syntheses of N-aryl-5,6,7-trimethoxyindoles as antimitotic and vascular disrupting agents: Application of the copper-mediated Ullmann-type arylation. Organic and Biomolecular Chemistry, 9(9), 3154-3157. https://doi.org/10.1039/c0ob01038c

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abstract = "In an attempt to mimic the 3,4,5-trimethoxyphenyl-Z-stilbene moiety of combretastatin A-4, a series of N-aryl-5,6,7-trimethoxyindoles were synthesized via copper-catalyzed Ullmann-type N-arylation through the corresponding 5,6,7-trimethoxyindole and aryl halides. These synthesized compounds demonstrated potent antiproliferative activity providing a novel skeleton for potent tubulin polymerization inhibitors.",

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T1 - Concise syntheses of N-aryl-5,6,7-trimethoxyindoles as antimitotic and vascular disrupting agents

T2 - Application of the copper-mediated Ullmann-type arylation

AU - Lee, Hsueh Yun

AU - Chang, Jang Yang

AU - Chang, Ling Yin

AU - Lai, Wen Yang

AU - Lai, Mei Jung

AU - Shih, Kuang Hsing

AU - Kuo, Ching Chuan

AU - Chang, Chi Yen

AU - Liou, Jing Ping

PY - 2011/5/7

Y1 - 2011/5/7

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AB - In an attempt to mimic the 3,4,5-trimethoxyphenyl-Z-stilbene moiety of combretastatin A-4, a series of N-aryl-5,6,7-trimethoxyindoles were synthesized via copper-catalyzed Ullmann-type N-arylation through the corresponding 5,6,7-trimethoxyindole and aryl halides. These synthesized compounds demonstrated potent antiproliferative activity providing a novel skeleton for potent tubulin polymerization inhibitors.

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Concise syntheses of N-aryl-5,6,7-trimethoxyindoles as antimitotic and vascular disrupting agents: Application of the copper-mediated Ullmann-type arylation

Abstract

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