(Z)-1-[4-(2-chloroethoxy)phenyl]-1-(4-fluorophenyl)-2-phenylprop-1-ene | 1449579-16-1

• 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: (Z)-1-[4-(2-chloroethoxy)phenyl]-1-(4-fluorophenyl)-2-phenylprop-1-ene
• 英文别名: 1-(2-chloroethoxy)-4-[(Z)-2-(4-fluorophenyl)-1-phenylprop-1-enyl]benzene
• CAS: 1449579-16-1
• 化学式: C₂₃H₂₀ClFO
• 分子量: 366.863
• InChiKey: JULVNUVWQXFKKG-QJOMJCCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  哌嗪 、 (Z)-1-[4-(2-chloroethoxy)phenyl]-1-(4-fluorophenyl)-2-phenylprop-1-ene 以 乙醇 为溶剂， 反应 24.0h， 以74%的产率得到(Z)-1-(2-{4-[2-(4-fluorophenyl)-1-phenyl-propenyl]-phenoxy}-ethyl) piperazine
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel triaryl (Z)-olefins as tamoxifen analogues

  摘要：

  Tamoxifen (TAM) is used for the treatment and prevention of estrogen receptor positive breast cancer. However, the limited activity, toxicity and the development of resistance raised the current need for new potent nontoxic antiestrogen. Six novel TAM analogues 5a-f were synthesized using McMurry olefination reaction. Replacement of the dimethylamino group in TAM by piperidino, piperazino or N-methyl piperazino, substituting the phenyl ring with florine atom at p-position and changing the ethyl group by methyl, afforded compounds showing comparable activity to TAM (1). Compounds 5c and 5e showed significant increase in antiproliferative activity in two breast cancer cell lines (MCF-7 and MDA-MB-231) compared to tamoxifen, while other compounds showed similar activity. The increased anticancer activity of compounds 5c and 5e was attributed to their ability to induce ER-independent cell death. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.056
• 作为产物：
  描述：

  4-(2-氯乙氧基)二苯甲酮 、 4-氟苯乙酮 在 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以40%的产率得到(Z)-1-[4-(2-chloroethoxy)phenyl]-1-(4-fluorophenyl)-2-phenylprop-1-ene
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel triaryl (Z)-olefins as tamoxifen analogues

  摘要：

  Tamoxifen (TAM) is used for the treatment and prevention of estrogen receptor positive breast cancer. However, the limited activity, toxicity and the development of resistance raised the current need for new potent nontoxic antiestrogen. Six novel TAM analogues 5a-f were synthesized using McMurry olefination reaction. Replacement of the dimethylamino group in TAM by piperidino, piperazino or N-methyl piperazino, substituting the phenyl ring with florine atom at p-position and changing the ethyl group by methyl, afforded compounds showing comparable activity to TAM (1). Compounds 5c and 5e showed significant increase in antiproliferative activity in two breast cancer cell lines (MCF-7 and MDA-MB-231) compared to tamoxifen, while other compounds showed similar activity. The increased anticancer activity of compounds 5c and 5e was attributed to their ability to induce ER-independent cell death. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.056

文献信息

• Design, synthesis and biological evaluation of novel triaryl (Z)-olefins as tamoxifen analogues
  作者：Khaled R.A. Abdellatif、Amany Belal、Hany A. Omar

  DOI：10.1016/j.bmcl.2013.06.056

  日期：2013.9

  Tamoxifen (TAM) is used for the treatment and prevention of estrogen receptor positive breast cancer. However, the limited activity, toxicity and the development of resistance raised the current need for new potent nontoxic antiestrogen. Six novel TAM analogues 5a-f were synthesized using McMurry olefination reaction. Replacement of the dimethylamino group in TAM by piperidino, piperazino or N-methyl piperazino, substituting the phenyl ring with florine atom at p-position and changing the ethyl group by methyl, afforded compounds showing comparable activity to TAM (1). Compounds 5c and 5e showed significant increase in antiproliferative activity in two breast cancer cell lines (MCF-7 and MDA-MB-231) compared to tamoxifen, while other compounds showed similar activity. The increased anticancer activity of compounds 5c and 5e was attributed to their ability to induce ER-independent cell death. (C) 2013 Elsevier Ltd. All rights reserved.