(E)-3-(5-bromo-1H-indol-3-yl)-1-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-2-en-1-one | 1416255-06-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (E)-3-(5-bromo-1H-indol-3-yl)-1-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-2-en-1-one
• CAS: 1416255-06-5
• 化学式: C₂₅H₂₆BrNO
• 分子量: 436.392
• InChiKey: KKBNLRGSKOBQPS-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,5-二氯-2,5-二甲基己烷 在 aluminum (III) chloride 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 生成 (E)-3-(5-bromo-1H-indol-3-yl)-1-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis, anticancer activities and molecular modeling studies of novel indole retinoid derivatives

  摘要：

  In this study, novel (E)-3-(5-substituted-1H-indol-3-yl)-1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-2-en-1-one (5(a-e)) derivatives were synthesized and their anticancer effects were determined in vitro. Novel indole retinoid compounds except Se have anti-proliferative capacity in liver, breast and colon cancer cell lines. This anti-proliferative effect was further analyzed in breast cancer cell line panel by using the most potent compound Sa. It was determined that 5a can inhibit proliferation at very low IC50 concentrations in all of the breast cancer cell lines. Here, we present some evidence on apoptotic termination of cancer cell proliferation which may be primarily driven by the inhibition of RXR alpha and, to a lesser extent, RXR gamma. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.013

文献信息

• Synthesis, anticancer activities and molecular modeling studies of novel indole retinoid derivatives
  作者：A. Selen Gurkan-Alp、Mine Mumcuoglu、Cenk A. Andac、Emre Dayanc、Rengul Cetin-Atalay、Erdem Buyukbingol

  DOI：10.1016/j.ejmech.2012.10.013

  日期：2012.12

  In this study, novel (E)-3-(5-substituted-1H-indol-3-yl)-1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-2-en-1-one (5(a-e)) derivatives were synthesized and their anticancer effects were determined in vitro. Novel indole retinoid compounds except Se have anti-proliferative capacity in liver, breast and colon cancer cell lines. This anti-proliferative effect was further analyzed in breast cancer cell line panel by using the most potent compound Sa. It was determined that 5a can inhibit proliferation at very low IC50 concentrations in all of the breast cancer cell lines. Here, we present some evidence on apoptotic termination of cancer cell proliferation which may be primarily driven by the inhibition of RXR alpha and, to a lesser extent, RXR gamma. (C) 2012 Elsevier Masson SAS. All rights reserved.