1,1-bis{4-[3-(dimethylamino)propoxy]phenyl}-2-phenyl-1-butene | 1020853-04-6

• 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: 1,1-bis{4-[3-(dimethylamino)propoxy]phenyl}-2-phenyl-1-butene
• 英文别名: 1,1-bis[4-(3-dimethylaminopropoxy)phenyl]-2-phenyl-but-1-ene；ridaifen G；3-[4-[1-[4-[3-(dimethylamino)propoxy]phenyl]-2-phenylbut-1-enyl]phenoxy]-N,N-dimethylpropan-1-amine
• CAS: 1020853-04-6
• 化学式: C₃₂H₄₂N₂O₂
• 分子量: 486.698
• InChiKey: RQSWTHUUSLNSOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  24.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  citric acid 、 1,1-bis{4-[3-(dimethylamino)propoxy]phenyl}-2-phenyl-1-butene 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.33h， 以95%的产率得到1,1-bis[4-(3-dimethylamoniumpropoxy)phenyl]-2-phenyl-but-1-ene citrate
  参考文献：
  名称：

  新型柠檬酸三芳基丁烯酯化合物的抗菌性能和作用方式

  摘要：

  这项研究的目的是评估他莫昔芬新合成的三芳基丁烯类似物的抗菌活性。合成了几种化合物并将其转化为柠檬酸盐以确保更高的溶解度。四种化合物在微摩尔浓度下对革兰氏阳性和革兰氏阴性食源性病原体表现出显着的抗菌活性，这些病原体包括单核细胞增生性李斯特菌，伊万氏李斯特菌，粪肠球菌，金黄色葡萄球菌和大肠杆菌。两种浓度为50μM的化合物仅引起7.8和11％的溶血。其中之一以及其余两个导致高K +和Na +从细菌细胞流出。使用透射电子显微镜还可以观察到超微结构的变化，这表明大肠杆菌的内膜或外膜受到了严重破坏。ivanovii L.显示出肿胀，起皱和类似的损坏，表明细胞壁完整性的丧失。有机金属化合物可能为新型抗菌化合物的设计提供有趣的机会。

  DOI：

  10.1016/j.ejmech.2014.02.037
• 作为产物：
  描述：

  N,N-二甲氨基氯丙烷盐酸盐 、 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 15.25h， 以94%的产率得到1,1-bis{4-[3-(dimethylamino)propoxy]phenyl}-2-phenyl-1-butene
  参考文献：
  名称：

  Ridaifen G, tamoxifen analog, is a potent anticancer drug working through a combinatorial association with multiple cellular factors

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2015.08.001

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。
• Antibacterial properties and mode of action of new triaryl butene citrate compounds
  作者：Mehdi El Arbi、Jérémie Théolier、Pascal Pigeon、Karim Jellali、Fatma Trigui、Siden Top、Sami Aifa、Ismail Fliss、Gérard Jaouen、Riadh Hammami

  DOI：10.1016/j.ejmech.2014.02.037

  日期：2014.4

  The aim of this study was to evaluate the antibacterial activity of newly synthesized triaryl butene analogues of tamoxifen. Several compounds were synthesized and converted to citrate salts to ensure greater solubility. Four compounds showed significant antibacterial activity at micromolar concentrations against Gram-positive and Gram-negative foodborne pathogens including Listeria monocytogenes,

  这项研究的目的是评估他莫昔芬新合成的三芳基丁烯类似物的抗菌活性。合成了几种化合物并将其转化为柠檬酸盐以确保更高的溶解度。四种化合物在微摩尔浓度下对革兰氏阳性和革兰氏阴性食源性病原体表现出显着的抗菌活性，这些病原体包括单核细胞增生性李斯特菌，伊万氏李斯特菌，粪肠球菌，金黄色葡萄球菌和大肠杆菌。两种浓度为50μM的化合物仅引起7.8和11％的溶血。其中之一以及其余两个导致高K +和Na +从细菌细胞流出。使用透射电子显微镜还可以观察到超微结构的变化，这表明大肠杆菌的内膜或外膜受到了严重破坏。ivanovii L.显示出肿胀，起皱和类似的损坏，表明细胞壁完整性的丧失。有机金属化合物可能为新型抗菌化合物的设计提供有趣的机会。
• 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.