(E)-3-(3-oxo-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-1-enyl)benzonitrile | 1261244-47-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-(3-oxo-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-1-enyl)benzonitrile
• 英文别名: 3-[(E)-3-oxo-3-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)prop-1-enyl]benzonitrile
• CAS: 1261244-47-6
• 化学式: C₂₅H₂₇NO
• 分子量: 357.495
• InChiKey: ZNBAFWVRCLEBNT-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-氰基苯甲醛 、 1-(5,6,7,8-四氢-3,5,5,8,8-五甲基-2-萘基)乙烷-1-酮 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 以11%的产率得到(E)-3-(3-oxo-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-1-enyl)benzonitrile
  参考文献：
  名称：

  Synthesis and biological evaluation of retinoid-chalcones as inhibitors of colon cancer cell growth

  摘要：

  Based on the observed anticancer activity of chalcones and retinoids, a novel class of retinoid-chalcone hybrids was designed and synthesized. As part of our ongoing studies to discover natural product based anticancer compounds, the retinoid-chalcone hybrids were tested against the colon cancer cell line HT-29. Retinoid like moiety was introduced through Friedel-Crafts alkylation of toluene. Among the synthesized compounds, the cyano derivative (E)-3-(3-oxo-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetra-hydronaphthalen-2-yl) prop-1-enyl) benzonitrile 8 showed submicromolar inhibitory activity with an IC50 of 0.66 mu M. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.10.038

文献信息

• Synthesis and biological evaluation of retinoid-chalcones as inhibitors of colon cancer cell growth
  作者：Cassia S. Mizuno、Shiby Paul、Nanjoo Suh、Agnes M. Rimando

  DOI：10.1016/j.bmcl.2010.10.038

  日期：2010.12

  Based on the observed anticancer activity of chalcones and retinoids, a novel class of retinoid-chalcone hybrids was designed and synthesized. As part of our ongoing studies to discover natural product based anticancer compounds, the retinoid-chalcone hybrids were tested against the colon cancer cell line HT-29. Retinoid like moiety was introduced through Friedel-Crafts alkylation of toluene. Among the synthesized compounds, the cyano derivative (E)-3-(3-oxo-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetra-hydronaphthalen-2-yl) prop-1-enyl) benzonitrile 8 showed submicromolar inhibitory activity with an IC50 of 0.66 mu M. Published by Elsevier Ltd.