(E)-1-(4-hydroxy-3-methoxy-5-((4-(4-((E)-3-(thiophen-2-yl)acryloyl)phenyl)piperazin-1-yl)methyl)phenyl)-3-(thiophen-2-yl)prop-2-en-1-one | 1292319-49-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (E)-1-(4-hydroxy-3-methoxy-5-((4-(4-((E)-3-(thiophen-2-yl)acryloyl)phenyl)piperazin-1-yl)methyl)phenyl)-3-(thiophen-2-yl)prop-2-en-1-one
• 英文别名: (E)-1-[4-[4-[[2-hydroxy-3-methoxy-5-[(E)-3-thiophen-2-ylprop-2-enoyl]phenyl]methyl]piperazin-1-yl]phenyl]-3-thiophen-2-ylprop-2-en-1-one
• CAS: 1292319-49-3
• 化学式: C₃₂H₃₀N₂O₄S₂
• 分子量: 570.733
• InChiKey: WVLJABYJHCOJBO-DCIPZJNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  香草乙酮 在 potassium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 24.5h， 生成 (E)-1-(4-hydroxy-3-methoxy-5-((4-(4-((E)-3-(thiophen-2-yl)acryloyl)phenyl)piperazin-1-yl)methyl)phenyl)-3-(thiophen-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  New bichalcone analogs as NF-κB inhibitors and as cytotoxic agents inducing Fas/CD95-dependent apoptosis

  摘要：

  A series of novel bichalcone analogs were synthesized and evaluated in lipopolysaccharide (LPS)-activated microglial cells as inhibitors of nitric oxide (NO) and for in vitro anticancer activity using a limited panel of four human cancer cell lines. All analogs inhibited NO production. Compounds 4 and 11 exhibited optimal activity with IC50 values of 0.3 and 0.5 mu M, respectively, and were at least 38-fold better than the positive control. A mechanism of action study showed that both compounds significantly blocked the nuclear translocation of NF-kappa B p65 and up-regulation of iNOS at 1.0 mu M. Compound 4 and three other analogs (3, 20, and 23) exerted significant in vitro anticancer activity GI(50) values ranging from 0.70 to 13.10 mu M. A mode of action study using HT-29 colon cancer cells showed that 23 acts by inducing apoptosis signaling. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.004

文献信息

• New bichalcone analogs as NF-κB inhibitors and as cytotoxic agents inducing Fas/CD95-dependent apoptosis
  作者：M. Vijaya Bhaskar Reddy、Yuh-Chiang Shen、Jai-Sing Yang、Tsong-Long Hwang、Kenneth F. Bastow、Keduo Qian、Kuo-Hsiung Lee、Tian-Shung Wu

  DOI：10.1016/j.bmc.2011.02.004

  日期：2011.3

  A series of novel bichalcone analogs were synthesized and evaluated in lipopolysaccharide (LPS)-activated microglial cells as inhibitors of nitric oxide (NO) and for in vitro anticancer activity using a limited panel of four human cancer cell lines. All analogs inhibited NO production. Compounds 4 and 11 exhibited optimal activity with IC50 values of 0.3 and 0.5 mu M, respectively, and were at least 38-fold better than the positive control. A mechanism of action study showed that both compounds significantly blocked the nuclear translocation of NF-kappa B p65 and up-regulation of iNOS at 1.0 mu M. Compound 4 and three other analogs (3, 20, and 23) exerted significant in vitro anticancer activity GI(50) values ranging from 0.70 to 13.10 mu M. A mode of action study using HT-29 colon cancer cells showed that 23 acts by inducing apoptosis signaling. (C) 2011 Elsevier Ltd. All rights reserved.