(E)-2-(2,4-dichlorobenzylidene)-1-(4-methoxyphenyl)-4-methylpentan-1-one

• 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)-2-(2,4-dichlorobenzylidene)-1-(4-methoxyphenyl)-4-methylpentan-1-one
• 英文别名: (2E)-2-[(2,4-dichlorophenyl)methylidene]-1-(4-methoxyphenyl)-4-methylpentan-1-one
• 化学式: C₂₀H₂₀Cl₂O₂
• 分子量: 363.284
• InChiKey: IKWUSMGZZYHPAY-LFIBNONCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-methoxy-4-(4-methylpent-1-yn-1-yl)benzene 、 2,4-二氯苯甲醛 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到(E)-2-(2,4-dichlorobenzylidene)-1-(4-methoxyphenyl)-4-methylpentan-1-one
  参考文献：
  名称：

  Synthesis and antiproliferative activity of α-branched α,β-unsaturated ketones in human hematological and solid cancer cell lines

  摘要：

  A series of alpha-branched alpha,beta-unsaturated ketones were prepared via boron trifluoride etherate mediated reaction between arylalkynes and carboxaldehydes. The evaluation of the antiproliferative activity over hematological (NB4) and solid cancer (A549, MCF-7) cell lines provided a structure-activity relationship. 5-Parameter QSAR equations were built which were able to explain 80%-92% of the variance in activity. The resulting selective lead compound showed IC50 value 0.6 mu M against the hematological cell line and did not cause apoptosis, but blocked cell cycle in G0/G1. Moreover, it was demonstrated that this compound enhances and accelerates retinoic acid induced granulocytic differentiation. (C) 2015 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2015.05.012

文献信息

• Synthesis and antiproliferative activity of α-branched α,β-unsaturated ketones in human hematological and solid cancer cell lines
  作者：Ieva Karpavičienė、Giedrė Valiulienė、Vytautas Raškevičius、Indrė Lebedytė、Algirdas Brukštus、Visvaldas Kairys、Rūta Navakauskienė、Inga Čikotienė

  DOI：10.1016/j.ejmech.2015.05.012

  日期：2015.6

  A series of alpha-branched alpha,beta-unsaturated ketones were prepared via boron trifluoride etherate mediated reaction between arylalkynes and carboxaldehydes. The evaluation of the antiproliferative activity over hematological (NB4) and solid cancer (A549, MCF-7) cell lines provided a structure-activity relationship. 5-Parameter QSAR equations were built which were able to explain 80%-92% of the variance in activity. The resulting selective lead compound showed IC50 value 0.6 mu M against the hematological cell line and did not cause apoptosis, but blocked cell cycle in G0/G1. Moreover, it was demonstrated that this compound enhances and accelerates retinoic acid induced granulocytic differentiation. (C) 2015 Published by Elsevier Masson SAS.