2-(3-benzyloxy-4-methoxy-phenyl)-3,5,7-trimethoxy-chromen-4-one | 209982-72-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(3-benzyloxy-4-methoxy-phenyl)-3,5,7-trimethoxy-chromen-4-one
• 英文别名: 2-(3-Benzyloxy-4-methoxy-phenyl)-3,5,7-trimethoxy-chromen-4-on；3,5,7-Trimethoxy-2-(4-methoxy-3-phenylmethoxyphenyl)chromen-4-one
• CAS: 209982-72-9
• 化学式: C₂₆H₂₄O₇
• 分子量: 448.472
• InChiKey: UMPFZLBRHLSJFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(3-benzyloxy-4-methoxy-phenyl)-3,5,7-trimethoxy-chromen-4-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以80%的产率得到3'-hydroxy-3,5,7,4'-tetramethoxyflavone
  参考文献：
  名称：

  Structure−Activity Requirements for Flavone Cytotoxicity and Binding to Tubulin

  摘要：

  A series of 79 flavones related to centaureidin (3,6,4'-trimethoxy-5,7,3'-trihydroxyflavone 1) was screened for cytotoxicity in the NCI in vitro 60-cell line human tumor screen. The resulting cytotoxicity profiles of these flavones were compared for degree of similarity to the profile of 1. Selected compounds were further evaluated with in vitro assays of tubulin polymerization and [H-3]colchicine binding to tubulin. Maximum potencies for tubulin interaction and production of differential cytotoxicity profiles characteristic of 1 were observed only with compounds containing hydroxyl substituents at C-3' and C-5 and methoxyl groups at C-3 and C-4'.

  DOI：

  10.1021/jm970842h
• 作为产物：
  描述：

  3,5-二甲氧基苯酚 在 盐酸 、 potassium 3-(benzyloxy)-4-methoxybenzoate 、 zinc(II) chloride 作用下， 以 乙醚 为溶剂， 生成 2-(3-benzyloxy-4-methoxy-phenyl)-3,5,7-trimethoxy-chromen-4-one
  参考文献：
  名称：

  Structure−Activity Requirements for Flavone Cytotoxicity and Binding to Tubulin

  摘要：

  A series of 79 flavones related to centaureidin (3,6,4'-trimethoxy-5,7,3'-trihydroxyflavone 1) was screened for cytotoxicity in the NCI in vitro 60-cell line human tumor screen. The resulting cytotoxicity profiles of these flavones were compared for degree of similarity to the profile of 1. Selected compounds were further evaluated with in vitro assays of tubulin polymerization and [H-3]colchicine binding to tubulin. Maximum potencies for tubulin interaction and production of differential cytotoxicity profiles characteristic of 1 were observed only with compounds containing hydroxyl substituents at C-3' and C-5 and methoxyl groups at C-3 and C-4'.

  DOI：

  10.1021/jm970842h

文献信息

• King et al., Journal of the Chemical Society, 1952, p. 96,100
  作者：King et al.

  DOI：——

  日期：——
• Structure−Activity Requirements for Flavone Cytotoxicity and Binding to Tubulin
  作者：John A. Beutler、Ernest Hamel、Arnold J. Vlietinck、Achiel Haemers、Padinchare Rajan、James N. Roitman、John H. Cardellina、Michael R. Boyd

  DOI：10.1021/jm970842h

  日期：1998.6.1

  A series of 79 flavones related to centaureidin (3,6,4'-trimethoxy-5,7,3'-trihydroxyflavone 1) was screened for cytotoxicity in the NCI in vitro 60-cell line human tumor screen. The resulting cytotoxicity profiles of these flavones were compared for degree of similarity to the profile of 1. Selected compounds were further evaluated with in vitro assays of tubulin polymerization and [H-3]colchicine binding to tubulin. Maximum potencies for tubulin interaction and production of differential cytotoxicity profiles characteristic of 1 were observed only with compounds containing hydroxyl substituents at C-3' and C-5 and methoxyl groups at C-3 and C-4'.