(Z)-2-(4-chlorobenzoyl)-3-(2,4-dichlorophenyl)allyl acetate

• 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: (Z)-2-(4-chlorobenzoyl)-3-(2,4-dichlorophenyl)allyl acetate
• 化学式: C₁₈H₁₃Cl₃O₃
• 分子量: 383.658
• InChiKey: BSAWZSUIMLZPJQ-ZSOIEALJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2,4-二氯苯甲醛 、 3-(4-chlorophenyl)prop-2-ynyl acetate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以30%的产率得到(E)-2-(4-chlorobenzoyl)-3-(2,4-dichlorophenyl)allyl acetate
  参考文献：
  名称：

  Synthesis and antiproliferative activity of α-branched α,β-unsaturated ketones

  摘要：

  A series of alpha-branched alpha,beta-unsaturated ketones were prepared in a straightforward manner by the acid catalyzed coupling between arylalkynes and carbaldehydes. The method also allows producing as side product chalcone analogs bearing an additional alpha,beta-unsaturated arylketone in the molecular scaffold. The evaluation of the antiproliferative activity in the human solid tumor cell lines HBL-100 (breast), HBL (cervix), SW1573 (non-small cell lung), T-47D (breast) and WiDr (colon) provided a structure activity relationship. Overall, the compounds presented active against the resistant cancer cells T-47D. The resulting lead, displaying an unprecedented chalcone scaffold, showed GI(50) values in the range 0.32-0.53 mu M against all cell lines tested. The methoxy group present in the lead might play an important role in the activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.041