1-hydroxy-4-(3-oxo-3-phenyl-propenyl)-naphthalene-2-carbaldehyde | 1287259-33-9

• 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: 1-hydroxy-4-(3-oxo-3-phenyl-propenyl)-naphthalene-2-carbaldehyde
• CAS: 1287259-33-9
• 化学式: C₂₀H₁₄O₃
• 分子量: 302.329
• InChiKey: AXJYBMYDPQEVFD-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-hydroxy-4-(3-oxo-3-phenyl-propenyl)-naphthalene-2-carbaldehyde 、 乙酰乙酸乙酯 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以85%的产率得到(E)-3-acetyl-6-(3-oxo-3-phenylprop-1-enyl)-2H-benzo[h]chromen-2-one
  参考文献：
  名称：

  Synthesis and in vitro evaluation of novel coumarin–chalcone hybrids as potential anticancer agents

  摘要：

  A series of coumarin-chalcone hybrids have been synthesized and evaluated for their in vitro cytotoxicity against a panel of four human cancer cell lines and normal fibroblasts (NIH3T3). Among 21 compounds screened, three compounds (23, 25 and 26) showed IC50 range from 3.59 to 8.12 mu M. The most promising compound 26 showed around 30-fold more selectivity towards C33A (cervical carcinoma) cells over normal fibroblast NIH3T3 cells with an IC50 value of 3.59 mu M. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.116
• 作为产物：
  描述：

  萘酚 在 盐酸 、 三氟乙酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 生成 1-hydroxy-4-(3-oxo-3-phenyl-propenyl)-naphthalene-2-carbaldehyde
  参考文献：
  名称：

  In vitro and in vivo antifilarial activity evaluation of 3,6-epoxy [1,5]dioxocines: A new class of antifilarial agents

  摘要：

  A series of 3,6-epoxy [1,5] dioxocines were synthesized and evaluated for their antifilarial activity against adult parasites of human lymphatic filarial parasite Brugia malayi (sub-periodic strain) in vitro. Out of these, six compounds (4a-f) possessed improved in vitro anti-filarial activity and examples 4d and 4f were also found to be active in the in vivo experiments. These results demonstrate that 3,6-epoxy [1,5] dioxocines exhibits potent antifilarial activity and might be developed into a new class of antifilarial drug. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.009