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 journalArticle

17 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 languageEnglish
Pages (from-to)3154-3157
Number of pages4
JournalOrganic and Biomolecular Chemistry
Volume9
Issue number9
DOIs
Publication statusPublished - May 7 2011

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Tubulin Modulators
Antimitotic Agents
disrupting
Stilbenes
stilbene
musculoskeletal system
Skeleton
inhibitors
halides
Blood Vessels
Copper
polymerization
copper
synthesis
fosbretabulin

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

Cite this

Concise syntheses of N-aryl-5,6,7-trimethoxyindoles as antimitotic and vascular disrupting agents : Application of the copper-mediated Ullmann-type arylation. / Lee, Hsueh Yun; Chang, Jang-Yang; Chang, Ling-Yin; Lai, Wen-Yang; Lai, Mei-Jung; Shih, Kuang-Hsing; Kuo, Ching-Chuan; Chang, Chi-Yen; Liou, Jing Ping.

In: Organic and Biomolecular Chemistry, Vol. 9, No. 9, 07.05.2011, p. 3154-3157.

Research output: Contribution to journalArticle

Lee, Hsueh Yun ; Chang, Jang-Yang ; Chang, Ling-Yin ; Lai, Wen-Yang ; Lai, Mei-Jung ; Shih, Kuang-Hsing ; Kuo, Ching-Chuan ; Chang, Chi-Yen ; Liou, Jing Ping. / Concise syntheses of N-aryl-5,6,7-trimethoxyindoles as antimitotic and vascular disrupting agents : Application of the copper-mediated Ullmann-type arylation. In: Organic and Biomolecular Chemistry. 2011 ; Vol. 9, No. 9. pp. 3154-3157.
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