2-[3-(benzyloxy)phenyl]-1,1-bis(4-hydroxyphenyl)-1-butene | 1416136-82-7

• 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-[3-(benzyloxy)phenyl]-1,1-bis(4-hydroxyphenyl)-1-butene
• 英文别名: 4-[1-(4-Hydroxyphenyl)-2-(3-phenylmethoxyphenyl)but-1-enyl]phenol；4-[1-(4-hydroxyphenyl)-2-(3-phenylmethoxyphenyl)but-1-enyl]phenol
• CAS: 1416136-82-7
• 化学式: C₂₉H₂₆O₃
• 分子量: 422.524
• InChiKey: LGWXRBDAUDAQFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[3-(benzyloxy)phenyl]-1,1-bis(4-hydroxyphenyl)-1-butene 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 2-甲基-6-硝基苯甲酸酐 、 氢气 、 sodium hydride 、 三乙胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 117.25h， 生成 2-[3-(N-biotinyl-6-aminohexanoyl)phenyl]-1,1-bis{4-[2-(morpholin-4-yl)ethoxy]phenyl}-1-butene
  参考文献：
  名称：

  [EN] GRB10 INTERACTING GYF PROTEIN 2 MODULATOR
  [FR] MODULATEUR DE PROTÉINE 2 GYF INTERAGISSANT AVEC GRB10

  摘要：

  一种包含GIGYF2调制剂，其有效成分为以下式子（I）所表示的化合物，其中在式子（I）中，R1和R2各自独立地表示氢原子或具有1至6个碳原子的烷基基团，或者R1和R2可以结合在一起形成一个带有氮原子的环状基团；n表示2至6的整数。

  公开号：

  WO2014061821A1
• 作为产物：
  描述：

  4,4'-二羟基二苯甲酮 、 1-(3-benzyloxyphenyl)propan-2-one 在 四氯化钛 、 potassium carbonate 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以94%的产率得到2-[3-(benzyloxy)phenyl]-1,1-bis(4-hydroxyphenyl)-1-butene
  参考文献：
  名称：

  Ridaifen B, a tamoxifen derivative, directly binds to Grb10 interacting GYF protein 2

  摘要：

  Ridaifen B (RID-B) is a tamoxifen derivative that potently inhibits breast tumor growth. RID-B was reported to show anti-proliferating activity for a variety of estrogen receptor (ER)-positive human cancer cells. Interestingly, RID-B was also reported to possess higher potency than that of tamoxifen even for some ER-negative cells, suggesting an ER-independent mechanism of action. In this study, a T7 phage display screen and subsequent binding analyses have identified Grb10 interacting GYF protein 2 (GIGYF2) as a RID-B-binding protein. Using a cell-based assay, the Akt phosphorylation level mediated by GIGYF2 was found to have decreased in the presence of RID-B. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.10.037

文献信息

• [EN] GRB10 INTERACTING GYF PROTEIN 2 MODULATOR<br/>[FR] MODULATEUR DE PROTÉINE 2 GYF INTERAGISSANT AVEC GRB10
  申请人：UNIV TOKYO SCIENCE FOUNDATION

  公开号：WO2014061821A1

  公开（公告）日：2014-04-24

  A GIGYF2 modulator including, as an active ingredient, a compound represented by the following Formula (I): wherein, in Formula (I), R1 and R2 each independently represent a hydrogen atom or an alkyl group having from 1 to 6 carbon atoms, or R1 and R2 may bind together to form a cyclic group with a nitrogen atom attached thereto; and n represents an integer from 2 to 6.

  一种包含GIGYF2调制剂，其有效成分为以下式子（I）所表示的化合物，其中在式子（I）中，R1和R2各自独立地表示氢原子或具有1至6个碳原子的烷基基团，或者R1和R2可以结合在一起形成一个带有氮原子的环状基团；n表示2至6的整数。
• Ridaifen G, tamoxifen analog, is a potent anticancer drug working through a combinatorial association with multiple cellular factors
  作者：Kentaro Ikeda、Shinji Kamisuki、Shoko Uetake、Akihito Mizusawa、Nozomi Ota、Tatsuki Sasaki、Senko Tsukuda、Tomoe Kusayanagi、Yoichi Takakusagi、Kengo Morohashi、Takao Yamori、Shingo Dan、Isamu Shiina、Fumio Sugawara

  DOI：10.1016/j.bmc.2015.08.001

  日期：2015.9

  Ridaifen-G (RID-G), a tamoxifen analog that we previously synthesized, has potent growth inhibitory activity against various cancer cell lines. Tamoxifen is an anticancer drug known to act on an estrogen receptor (ER) and other proteins. However, our previous studies interestingly suggested that the mechanism of action of RID-G was different from that of tamoxifen. In order to investigate the molecular mode of action of RID-G, we developed a novel chemical genetic approach that combined a phage display screen with a statistical analysis of drug potency and gene expression profiles in thirty-nine cancer cell lines. Application of this method to RID-G revealed that three proteins, calmodulin (CaM), heterogeneous nuclear ribonucleoproteins A2/B1 (hnRNP A2/B1), and zinc finger protein 638 (ZNF638) were the candidates of direct targets of RID-G. Moreover, cell lines susceptible to RID-G show similar expression profiles of RID-G target genes. These results suggest that RID-G involves CaM, hnRNP A2/B1, and ZNF638 in its growth inhibitory activity. (c) 2015 Published by Elsevier Ltd.
• Ridaifen B, a tamoxifen derivative, directly binds to Grb10 interacting GYF protein 2
  作者：Senko Tsukuda、Tomoe Kusayanagi、Eri Umeda、Chihiro Watanabe、Yu-ta Tosaki、Shinji Kamisuki、Toshifumi Takeuchi、Yoichi Takakusagi、Isamu Shiina、Fumio Sugawara

  DOI：10.1016/j.bmc.2012.10.037

  日期：2013.1

  Ridaifen B (RID-B) is a tamoxifen derivative that potently inhibits breast tumor growth. RID-B was reported to show anti-proliferating activity for a variety of estrogen receptor (ER)-positive human cancer cells. Interestingly, RID-B was also reported to possess higher potency than that of tamoxifen even for some ER-negative cells, suggesting an ER-independent mechanism of action. In this study, a T7 phage display screen and subsequent binding analyses have identified Grb10 interacting GYF protein 2 (GIGYF2) as a RID-B-binding protein. Using a cell-based assay, the Akt phosphorylation level mediated by GIGYF2 was found to have decreased in the presence of RID-B. (C) 2012 Elsevier Ltd. All rights reserved.