1-(2-hydroxyphenyl)-4-methylpent-1-en-3-one | 202409-10-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-(2-hydroxyphenyl)-4-methylpent-1-en-3-one
• CAS: 202409-10-7
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: UDADFGGJNXJEEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3,3-二甲基-2,4-戊二酮 、 水杨醛 在 barium hydroxide octahydrate 作用下， 以 甲醇 为溶剂， 生成 1-(2-hydroxyphenyl)-4-methylpent-1-en-3-one
  参考文献：
  名称：

  2-Hydroxycurcuminoid induces apoptosis of human tumor cells through the reactive oxygen species–mitochondria pathway

  摘要：

  2-Hydroxycinnamaldehyde (HCA) and curcumin have been reported to have antitumor effects against various human tumor cells in vitro and in vivo by generation of ROS. Aldehyde-free HCA analogs were synthesized based on the structure of curcumin, which we have called 2-hydroxycurcuminoids. The hydroxyl group of curcuminoids enhances the ability to generate ROS. 2-Hydroxycurcuminoid (HCC-7) strongly inhibited the growth of SW620 colon tumor cells with a GI(50) value of 7 mu M, while the parent compounds, HCA and curcumin, displayed GI(50) values of 12 and 30 mu M, respectively. HCC-7 was found to induce apoptosis through the reactive oxygen species-mitochondria pathway and cell cycle arrest at G2/M phase. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.114

文献信息

• 2-Hydroxycurcuminoid induces apoptosis of human tumor cells through the reactive oxygen species–mitochondria pathway
  作者：Young-Min Han、Dae-Seop Shin、Yu-Jin Lee、Ismail Ahmed Ismail、Su-Hyung Hong、Dong Cho Han、Byoung-Mog Kwon

  DOI：10.1016/j.bmcl.2010.11.114

  日期：2011.1

  2-Hydroxycinnamaldehyde (HCA) and curcumin have been reported to have antitumor effects against various human tumor cells in vitro and in vivo by generation of ROS. Aldehyde-free HCA analogs were synthesized based on the structure of curcumin, which we have called 2-hydroxycurcuminoids. The hydroxyl group of curcuminoids enhances the ability to generate ROS. 2-Hydroxycurcuminoid (HCC-7) strongly inhibited the growth of SW620 colon tumor cells with a GI(50) value of 7 mu M, while the parent compounds, HCA and curcumin, displayed GI(50) values of 12 and 30 mu M, respectively. HCC-7 was found to induce apoptosis through the reactive oxygen species-mitochondria pathway and cell cycle arrest at G2/M phase. (C) 2010 Elsevier Ltd. All rights reserved.