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

研究成果: 雜誌貢獻文章

7 引文 (Scopus)

摘要

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.

原文英語
頁(從 - 到)306-314
頁數9
期刊European Journal of Medicinal Chemistry
77
DOIs
出版狀態已發佈 - 四月 22 2014

指紋

Benzophenones
Antimitotic Agents
KB Cells
Endothelial cells
Human Umbilical Vein Endothelial Cells
Hydrogen Bonding
Tubulin
Blood Vessels
Hydrogen bonds
(3-hydroxy-4-methoxyphenyl)(2-hydroxy-3,4,5-trimethoxyphenyl)methanone
fosbretabulin

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Pharmacology
  • Medicine(all)

引用此文

Antimitotic and vascular disrupting agents : 2-Hydroxy-3,4,5- trimethoxybenzophenones. / Chang, Chih Yi; Chuang, Hsun Yueh; Lee, Hsueh Yun; Yeh, Teng Kuang; Kuo, Ching Chuan; Chang, Chi Yen; Chang, Jang Yang; Liou, Jing Ping.

於: European Journal of Medicinal Chemistry, 卷 77, 22.04.2014, p. 306-314.

研究成果: 雜誌貢獻文章

Chang, Chih Yi ; Chuang, Hsun Yueh ; Lee, Hsueh Yun ; Yeh, Teng Kuang ; Kuo, Ching Chuan ; Chang, Chi Yen ; Chang, Jang Yang ; Liou, Jing Ping. / Antimitotic and vascular disrupting agents : 2-Hydroxy-3,4,5- trimethoxybenzophenones. 於: European Journal of Medicinal Chemistry. 2014 ; 卷 77. 頁 306-314.
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AB - 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.

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