Antimitotic and antivascular activity of heteroaroyl-2-hydroxy-3,4,5-trimethoxybenzenes

Hsueh Yun Lee, Chih-Yi Chang, Mei-Jung Lai, Hsun-Yueh Chuang, Ching-Chuan Kuo, Chi-Yen Chang, Jang-Yang Chang, Jing Ping Liou

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

This study reports the synthesis of a series of heteroaroyl-2-hydroxy-3,4,5-trimethoxybenzenes, which are potent antitubulin agents. Compound 13, (2-hydroxy-3,4,5-trimethoxyphenyl)-(6-methoxy-1H-indol-3-yl)-methanone exhibits marked antiproliferative activity against KB and MKN45 cells with IC50 values of 8.8 and 10.5 nM, respectively, binds strongly to the colchicine binding site and leads to inhibition of tubulin polymerization. It also behaves as a vascular disrupting agent which suppresses the formation of capillaries. The C2-OH group in the A-ring of this compound not only retains the biological activity but has valuable physicochemical properties.

Original languageEnglish
Pages (from-to)4230-4236
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume23
Issue number15
DOIs
Publication statusPublished - Jul 23 2015

Keywords

  • Antiproliferative
  • CA-4
  • Vascular-disrupting agents

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Molecular Biology
  • Molecular Medicine
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

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