1-(4-hydroxyphenyl)-1,2-bis(4-trimethylacetoxyphenyl)but-1-ene | 1133415-48-1

• 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: 1-(4-hydroxyphenyl)-1,2-bis(4-trimethylacetoxyphenyl)but-1-ene
• 英文别名: 1-(p-hydroxyphenyl)-1,2-di(p-trimethylacetoxyphenyl)but-1-ene；2,2-Dimethylpropanoic Acid 1,1'-[[1-Ethyl-2-(4-hydroxyphenyl)-1,2-ethenediyl]di-4,1-phenylene] Ester；[4-[1-[4-(2,2-dimethylpropanoyloxy)phenyl]-1-(4-hydroxyphenyl)but-1-en-2-yl]phenyl] 2,2-dimethylpropanoate
• CAS: 1133415-48-1
• 化学式: C₃₂H₃₆O₅
• 分子量: 500.635
• InChiKey: KJQBTKFJMMJROZ-UHFFFAOYSA-N

物化性质

• 沸点：
  588.3±45.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮、氯仿、DCM

计算性质

• 辛醇/水分配系数(LogP)：
  7.66
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(4-hydroxyphenyl)-1,2-bis(4-trimethylacetoxyphenyl)but-1-ene 、 2-chloro-1-ferrocenylethanone 在 KH 作用下， 以 四氢呋喃 为溶剂， 以41%的产率得到(C2H5)(C(p-trimethylacetoxyphenyl))2OCH2CO[(η5-C5H4)FeCp]
  参考文献：
  名称：

  Organometallic analogues of tamoxifen: Effect of the amino side-chain replacement by a carbonyl ferrocenyl moiety in hydroxytamoxifen

  摘要：

  Since the widely prescribed selective estrogen receptor modulator (SERM) tamoxifen encounters growing cases of resistance in long-term treatments, alternative drugs with different therapeutic scopes have to be developed. Many investigators have modified the triphenylethylene scaffold, but very few have changed its amino side chain, essential for the antiestrogenic activity. For the first time, a lipophilic and stable organometallic entity, -OCH2CO-[(eta(5)-C5H4)FeCp], has replaced this key functional side chain, while keeping a good affinity for the estrogen receptor and an antiproliferative activity on cancer cells (MCF-7 and PC-3). Its mechanism of action is likely to be different from the antihormonal pathway followed by hydroxytamoxifen, and from the cytotoxicity observed for the ferrocifens. (C) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.11.016
• 作为产物：
  描述：

  4,4'-二羟基二苯甲酮 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 1-(4-hydroxyphenyl)-1,2-bis(4-trimethylacetoxyphenyl)but-1-ene
  参考文献：
  名称：

  Organometallic analogues of tamoxifen: Effect of the amino side-chain replacement by a carbonyl ferrocenyl moiety in hydroxytamoxifen

  摘要：

  Since the widely prescribed selective estrogen receptor modulator (SERM) tamoxifen encounters growing cases of resistance in long-term treatments, alternative drugs with different therapeutic scopes have to be developed. Many investigators have modified the triphenylethylene scaffold, but very few have changed its amino side chain, essential for the antiestrogenic activity. For the first time, a lipophilic and stable organometallic entity, -OCH2CO-[(eta(5)-C5H4)FeCp], has replaced this key functional side chain, while keeping a good affinity for the estrogen receptor and an antiproliferative activity on cancer cells (MCF-7 and PC-3). Its mechanism of action is likely to be different from the antihormonal pathway followed by hydroxytamoxifen, and from the cytotoxicity observed for the ferrocifens. (C) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.11.016

文献信息

• Synthesis and Structure-Activity Relationships of Ferrocenyl Tamoxifen Derivatives with Modified Side Chains
  作者：Anh Nguyen、Siden Top、Pascal Pigeon、Anne Vessières、Elizabeth A. Hillard、Marie-Aude Plamont、Michel Huché、Clara Rigamonti、Gérard Jaouen

  DOI：10.1002/chem.200801108

  日期：2009.1.5

  experimental binding affinity results for compounds 2, 2 a, 2 b, 5, 5 a, and 5 b. Electrochemical experiments show that 1–4, 2 a, and 2 b are stable to oxidation on the electrochemical timescale, unlike 5, 5 a, and 5 b, and that cytotoxicity is related to less positive phenol oxidation potentials. The SAR study shows that the presence of a ketone group and two phenol groups is necessary for strong receptor

  我们在此报告乳腺癌药物他莫昔芬衍生物的合成和细胞增殖特性，其中负责该药物抗雌激素特性的O（CH 2）2 N（CH 3）2侧链已被α二茂铁基部分。我们最近报道的二酚化合物5，其中该氨基酸链已被替换为酰基二茂铁（ O（CH 2）2 C（O）[（η 5 -C 5 H ^ 4）（FeCp]）组，并且对激素依赖性MCF-7和非依赖性MDA-MB-231乳腺癌细胞系均具有抗增殖作用。现在，我们报告结构-活性关系（SAR）研究的结果，其中侧链长度已变化，酮基已被省略，苯酚基团的数目已变化。化合物1 - 4，具有侧链缺乏羰基函数（ O（CH 2）Ñ [（η 5 -C 5 H ^ 4）FeCp]，Ñ= 1–4），并且随着链长的增加，其对ERα的亲和力降低（ER =雌激素受体），对MCF-7细胞起雌激素作用，对PC-3前列腺癌细胞起轻度细胞毒性作用，IC 50值约为10 μ中号。的两个单酚类衍生物2，2
• Organometallic analogues of tamoxifen: Effect of the amino side-chain replacement by a carbonyl ferrocenyl moiety in hydroxytamoxifen
  作者：Anh Nguyen、Siden Top、Anne Vessières、Pascal Pigeon、Michel Huché、Elizabeth A. Hillard、Gérard Jaouen

  DOI：10.1016/j.jorganchem.2006.11.016

  日期：2007.2

  Since the widely prescribed selective estrogen receptor modulator (SERM) tamoxifen encounters growing cases of resistance in long-term treatments, alternative drugs with different therapeutic scopes have to be developed. Many investigators have modified the triphenylethylene scaffold, but very few have changed its amino side chain, essential for the antiestrogenic activity. For the first time, a lipophilic and stable organometallic entity, -OCH2CO-[(eta(5)-C5H4)FeCp], has replaced this key functional side chain, while keeping a good affinity for the estrogen receptor and an antiproliferative activity on cancer cells (MCF-7 and PC-3). Its mechanism of action is likely to be different from the antihormonal pathway followed by hydroxytamoxifen, and from the cytotoxicity observed for the ferrocifens. (C) 2006 Elsevier B.V. All rights reserved.