N-[2-[4-[(Z)-1,2-diphenylbut-1-enyl]phenoxy]ethyl]-N-methylacetamide

• 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: N-[2-[4-[(Z)-1,2-diphenylbut-1-enyl]phenoxy]ethyl]-N-methylacetamide
• 化学式: C₂₇H₂₉NO₂
• 分子量: 399.533
• InChiKey: REKOXFJLLJWNFA-RQZHXJHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[2-[4-[(Z)-1,2-diphenylbut-1-enyl]phenoxy]ethyl]-N-methylacetamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以71%的产率得到methyltamoxifen
  参考文献：
  名称：

  Loss of antagonistic activity of tamoxifen by replacement of one N-methyl of its side chain by fluorinated residues

  摘要：

  Efforts to limit the metabolic alteration of the aminoalkyl side chain of tamoxifen by fluorination largely decrease its ER-mediated antagonistic properties in MCF-7 cells (i.e., ability to inhibit growth, to stabilize ER, and to modulate ERE and AP-1 transcriptional activity). This loss is associated with an enhancement of agonistic activity. Loss of interaction between Asp 351 and the nitrogen atom of tamoxifen provoked by the fluorination of its side chain may explain this property. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.012
• 作为产物：
  描述：

  N-去甲他莫昔芬盐酸盐 、 乙酸酐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以83%的产率得到N-[2-[4-[(Z)-1,2-diphenylbut-1-enyl]phenoxy]ethyl]-N-methylacetamide
  参考文献：
  名称：

  Loss of antagonistic activity of tamoxifen by replacement of one N-methyl of its side chain by fluorinated residues

  摘要：

  Efforts to limit the metabolic alteration of the aminoalkyl side chain of tamoxifen by fluorination largely decrease its ER-mediated antagonistic properties in MCF-7 cells (i.e., ability to inhibit growth, to stabilize ER, and to modulate ERE and AP-1 transcriptional activity). This loss is associated with an enhancement of agonistic activity. Loss of interaction between Asp 351 and the nitrogen atom of tamoxifen provoked by the fluorination of its side chain may explain this property. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.012

文献信息

• Loss of antagonistic activity of tamoxifen by replacement of one N-methyl of its side chain by fluorinated residues
  作者：Vangelis Agouridas、Ioanna Laı¨os、Anny Cleeren、Elyane Kizilian、Emmanuel Magnier、Jean-Claude Blazejewski、Guy Leclercq

  DOI：10.1016/j.bmc.2006.07.012

  日期：2006.11

  Efforts to limit the metabolic alteration of the aminoalkyl side chain of tamoxifen by fluorination largely decrease its ER-mediated antagonistic properties in MCF-7 cells (i.e., ability to inhibit growth, to stabilize ER, and to modulate ERE and AP-1 transcriptional activity). This loss is associated with an enhancement of agonistic activity. Loss of interaction between Asp 351 and the nitrogen atom of tamoxifen provoked by the fluorination of its side chain may explain this property. (c) 2006 Elsevier Ltd. All rights reserved.