Antimitotic and vascular disrupting agents: 2-Hydroxy-3,4,5- trimethoxybenzophenones

Chih Yi Chang, Hsun Yueh Chuang, Hsueh Yun Lee, Teng Kuang Yeh, Ching Chuan Kuo, Chi Yen Chang, Jang Yang Chang, Jing Ping Liou

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)


2-Hydroxy-3,4,5-trimethoxybenzophenones (8-16) manifest pseudo-ring formation involving intramolecular hydrogen bonding of the 2-OH and the carbonyl group. Among the synthetic products described in this report, (3-hydroxy-4-methoxyphenyl)(2-hydroxy-3,4,5-trimethoxyphenyl)-methanone (14) and (3-amino-4-methoxyphenyl)(2-hydroxy-3,4,5-trimethoxy-phenyl)methanone (16) exhibit significant antiproliferative activity against KB cells with IC 50 values of 11.1 and 11.3 nM, respectively. These two compounds also displayed tubulin affinity comparable to that of combretastatin A-4. In studies with human umbilical vein endothelial cells, compounds 14 and 16 revealed concentration-dependent vascular-disrupting properties. The results support the rationale of the pseudo-ring concept and suggest further investigation of A-ring modification in these benzophenones.

Original languageEnglish
Pages (from-to)306-314
Number of pages9
JournalEuropean Journal of Medicinal Chemistry
Publication statusPublished - 2014 Apr 22

All Science Journal Classification (ASJC) codes

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry


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