2-phenyl-1,1-bis{4-[3-(pyrrolidin-1-yl)propoxy]phenyl}but-1-ene

• 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: 2-phenyl-1,1-bis{4-[3-(pyrrolidin-1-yl)propoxy]phenyl}but-1-ene
• 英文别名: 1-[3-[4-[2-Phenyl-1-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]but-1-enyl]phenoxy]propyl]pyrrolidine；1-[3-[4-[2-phenyl-1-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]but-1-enyl]phenoxy]propyl]pyrrolidine
• 化学式: C₃₆H₄₆N₂O₂
• 分子量: 538.773
• InChiKey: BSXJLKJQYUBCQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  24.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(3-氯丙基)吡咯烷盐酸盐 、 1,1-双(4-羟基苯基)-2-苯基丁-1-烯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 paraffin oil 为溶剂， 反应 11.25h， 以87%的产率得到2-phenyl-1,1-bis{4-[3-(pyrrolidin-1-yl)propoxy]phenyl}but-1-ene
  参考文献：
  名称：

  A novel tamoxifen derivative, ridaifen-F, is a nonpeptidic small-molecule proteasome inhibitor

  摘要：

  In a survey of nonpeptide noncovalent inhibitors of the human 20S proteasome, we found that a novel tamoxifen derivative, RID-F (compound 6), inhibits all three protease activities of the proteasome at submicromolar levels. Structure activity relationship studies revealed that a RID-F analog (RID-F-S*4, compound 25) is the smallest derivative compound capable of inhibiting proteasome activity, with a potency similar to that of RID-F. Kinetic analyses of the inhibition mode and competition experiments involving biotin-belactosin A (a proteasome inhibitor) binding indicated that the RID-F derivatives interact with the protease subunits in a different manner. Culturing of human cells with these compounds resulted in accumulation of ubiquitinated proteins and induction of apoptosis. Thus, the RID-F derivatives may be useful lead chemicals for the generation of a new class of proteasome inhibitors. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.11.009

文献信息

• [EN] BRAP2 ACTION ENHANCER<br/>[FR] AMPLIFICATEUR D'ACTION DE LA BRAP2<br/>[JA] ＢＲＡＰ２作用増強剤
  申请人：UNIV TOKYO SCIENCE FOUND

  公开号：WO2021075147A1

  公开（公告）日：2021-04-22

  下記式（１）又は（２）で表される化合物又はその塩を有効成分として含有する、Ｒａｓ／Ｒａｆ／ＭＥＫ／ＥＲＫ経路及びＰＩ３Ｋ／Ａｋｔ／ｍＴＯＲ経路の両者を阻害するのに有用な、新規のＢＲＡＰ２作用増強剤を提供する。
• A novel tamoxifen derivative, ridaifen-F, is a nonpeptidic small-molecule proteasome inhibitor
  作者：Makoto Hasegawa、Yukari Yasuda、Makoto Tanaka、Kenya Nakata、Eri Umeda、Yanwen Wang、Chihiro Watanabe、Shoko Uetake、Tatsuki Kunoh、Masafumi Shionyu、Ryuzo Sasaki、Isamu Shiina、Tamio Mizukami

  DOI：10.1016/j.ejmech.2013.11.009

  日期：2014.1

  In a survey of nonpeptide noncovalent inhibitors of the human 20S proteasome, we found that a novel tamoxifen derivative, RID-F (compound 6), inhibits all three protease activities of the proteasome at submicromolar levels. Structure activity relationship studies revealed that a RID-F analog (RID-F-S*4, compound 25) is the smallest derivative compound capable of inhibiting proteasome activity, with a potency similar to that of RID-F. Kinetic analyses of the inhibition mode and competition experiments involving biotin-belactosin A (a proteasome inhibitor) binding indicated that the RID-F derivatives interact with the protease subunits in a different manner. Culturing of human cells with these compounds resulted in accumulation of ubiquitinated proteins and induction of apoptosis. Thus, the RID-F derivatives may be useful lead chemicals for the generation of a new class of proteasome inhibitors. (C) 2013 Elsevier Masson SAS. All rights reserved.