(cis/trans)-1-(4-β-aminoethoxy-phenyl)-1,2-diphenyl-1-butene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (cis/trans)-1-(4-β-aminoethoxy-phenyl)-1,2-diphenyl-1-butene
• 英文别名: 2-(4-(1,2-diphenylbut-1-en-1-yl)phenoxy)ethan-1-amine；2-(4-(1,2-phenylbut-1-en-1-yl)phenoxy)ethan-1-amine；2-[4-(1,2-Diphenylbut-1-enyl)phenoxy]ethanamine
• 化学式: C₂₄H₂₅NO
• 分子量: 343.469
• InChiKey: MCJKBWHDNUSJLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  、 (cis/trans)-1-(4-β-aminoethoxy-phenyl)-1,2-diphenyl-1-butene 在 三乙胺 作用下， 反应 44.0h， 以42%的产率得到
  参考文献：
  名称：

  Rational design of ERα targeting hypoxia turn-on fluorescent probes with antiproliferative activity for breast cancer

  摘要：

  已开发出几种针对ERα的靶向缺氧开启荧光探针。探针3和5在MCF-7细胞中显示出良好的缺氧开启响应和良好的抗增殖活性，并且对正常细胞显示出低细胞毒性。

  DOI：

  10.1039/c9cc09754f
• 作为产物：
  描述：

  1-苯丙醇 在 吡啶 、 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 三氯异氰尿酸 、 四氯化钛 、 potassium carbonate 、 锌 作用下， 以 四氢呋喃 、 乙酸乙酯 、 丙酮 为溶剂， 反应 8.75h， 生成 (cis/trans)-1-(4-β-aminoethoxy-phenyl)-1,2-diphenyl-1-butene
  参考文献：
  名称：

  Rational design of ERα targeting hypoxia turn-on fluorescent probes with antiproliferative activity for breast cancer

  摘要：

  已开发出几种针对ERα的靶向缺氧开启荧光探针。探针3和5在MCF-7细胞中显示出良好的缺氧开启响应和良好的抗增殖活性，并且对正常细胞显示出低细胞毒性。

  DOI：

  10.1039/c9cc09754f

文献信息

• Reaction of Pyrylium Salts with Nucleophiles. 23: Triarylethene Derivatives Containing an Oxyalkyleneamino or Oxyalkylene-N-pyridinium Side Chain
  作者：Octavian Stanciuc、Alexandru T. Balaban

  DOI：10.1002/jps.2600820911

  日期：1993.9

  amines related to anticancer drugs clomiphene and tamoxifen on the basis of key intermediates with a phenolic group, to which a side chain (omega-aminoethoxy or omega-aminopropoxy) was attached. These compounds were then reacted with 2,4,6-trimethyl- or 2,4,6-triphenylpyrylium salts. This afforded pyridinium analogues of clomiphene and tamoxifen as potential therapeutic agents for treatment against hormone-dependent

  设计了一种合成设计，用于制备与抗癌药克罗米芬和他莫昔芬有关的伯胺，该伯胺的主要中间体是带有酚基的中间体，该中间体上连接有侧链（ω-氨基乙氧基或ω-氨基丙氧基）。然后使这些化合物与2,4,6-三甲基-或2,4,6-三苯基吡啶鎓盐反应。这提供了克罗米芬和他莫昔芬的吡啶鎓类似物作为针对激素依赖性肿瘤的潜在治疗剂。
• Design and Synthesis of Norendoxifen Analogues with Dual Aromatase Inhibitory and Estrogen Receptor Modulatory Activities
  作者：Wei Lv、Jinzhong Liu、Todd C. Skaar、David A. Flockhart、Mark Cushman

  DOI：10.1021/jm501218e

  日期：2015.3.26

  Both selective estrogen receptor modulators and aromatase inhibitors are widely used for the treatment of breast cancer. Compounds with both aromatase inhibitory and estrogen receptor modulatory activities could have special advantages for treatment of breast cancer. Our previous efforts led to the discovery of norendoxifen as the first compound with dual aromatase inhibitory and estrogen receptor binding activities. To optimize its efficacy and aromatase selectivity versus other cytochrome P450 enzyme, a series of structurally related norendoxifen analogues were designed and synthesized. The most potent compound, 4'-hydroxynorendoxifen (10), displayed elevated inhibitory potency against aromatase and enhanced affinity for estrogen receptors when compared to norendoxifen. The selectivity of 10 for aromatase versus other cytochrome P450 eniymes was also superior to norendoxifen. 4'-Hydroxynorendoxifen is therefore an interesting lead for further development to obtain new anticancer agents of potential value for the treatment of breast cancer.