(3-fluoro-4-methoxyphenyl)(2-hydroxy-3,4,5-trimethoxyphenyl)methanone | 1601474-86-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3-fluoro-4-methoxyphenyl)(2-hydroxy-3,4,5-trimethoxyphenyl)methanone
• 英文别名: (3-Fluoro-4-methoxyphenyl)-(2-hydroxy-3,4,5-trimethoxyphenyl)methanone；(3-fluoro-4-methoxyphenyl)-(2-hydroxy-3,4,5-trimethoxyphenyl)methanone
• CAS: 1601474-86-5
• 化学式: C₁₇H₁₇FO₆
• 分子量: 336.317
• InChiKey: JBEYBCKPCQJZCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-bromo-3,4,5-trimethoxy-2-(methoxymethoxy)benzene 在 盐酸 、 重铬酸吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (3-fluoro-4-methoxyphenyl)(2-hydroxy-3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

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

  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 IC50 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. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.061

文献信息

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

  DOI：10.1016/j.ejmech.2014.02.061

  日期：2014.4

  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 IC50 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. (C) 2014 Elsevier Masson SAS. All rights reserved.