(1E,4Z,6E)-5-hydroxy-7-(3,4,5-trimethoxyphenyl)-1-(2,6,6-trimethylcyclohexen-1-yl)hepta-1,4,6-trien-3-one | 1186127-03-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1E,4Z,6E)-5-hydroxy-7-(3,4,5-trimethoxyphenyl)-1-(2,6,6-trimethylcyclohexen-1-yl)hepta-1,4,6-trien-3-one
• CAS: 1186127-03-6
• 化学式: C₂₅H₃₂O₅
• 分子量: 412.526
• InChiKey: RFVUHNSTFLKGNH-LGUJZUIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (E)-6-(2,6,6-trimethylcyclohex-1-enyl)hex-5-ene-2,4-dione 、 3,4,5-三甲氧基苯甲醛 在 boron trioxide 、 硼酸三丁酯 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以32%的产率得到(1E,4Z,6E)-5-hydroxy-7-(3,4,5-trimethoxyphenyl)-1-(2,6,6-trimethylcyclohexen-1-yl)hepta-1,4,6-trien-3-one
  参考文献：
  名称：

  Design and Synthesis of Androgen Receptor Antagonists with Bulky Side Chains for Overcoming Antiandrogen Resistance

  摘要：

  Incorporation of curcumin and beta-ionone into one chemical entity led to identification of a novel antiandrogen with two bulky side chains, 6, which is a pure antagonist of the wild-type and the T877A, W741C, and H874Y mutated androgen receptors (AR), showing no cross-reactivity with progesterone receptor and low micromolar cytotoxicity in LNCaP, PCa-2b, 22Rv1, and C4-2B prostate cancer cells. Molecular modeling indicates 6 adopts a "Y"-shape conformation and forms multiple hydrogen bonds with AR backbone.

  DOI：

  10.1021/jm801218k

文献信息

• Design and Synthesis of Androgen Receptor Antagonists with Bulky Side Chains for Overcoming Antiandrogen Resistance
  作者：Jinming Zhou、Guoyan Geng、Qingwen Shi、Francoise Sauriol、Jian Hui Wu

  DOI：10.1021/jm801218k

  日期：2009.9.10

  Incorporation of curcumin and beta-ionone into one chemical entity led to identification of a novel antiandrogen with two bulky side chains, 6, which is a pure antagonist of the wild-type and the T877A, W741C, and H874Y mutated androgen receptors (AR), showing no cross-reactivity with progesterone receptor and low micromolar cytotoxicity in LNCaP, PCa-2b, 22Rv1, and C4-2B prostate cancer cells. Molecular modeling indicates 6 adopts a "Y"-shape conformation and forms multiple hydrogen bonds with AR backbone.