2',4',6'-tris(2-chlorobenzoyloxy)acetophenone | 920006-70-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 2',4',6'-tris(2-chlorobenzoyloxy)acetophenone
• 英文别名: [4-Acetyl-3,5-bis[(2-chlorobenzoyl)oxy]phenyl] 2-chlorobenzoate
• CAS: 920006-70-8
• 化学式: C₂₉H₁₇Cl₃O₇
• 分子量: 583.809
• InChiKey: YQOXXZJSNMQCDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2',4',6'-tris(2-chlorobenzoyloxy)acetophenone 在 吡啶 、 氢氧化钾 、 tin chloride hydrate 、 硝酸 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 12.75h， 生成 N-[2-(2-chlorophenyl)-5,7-dihydroxy-4-oxochromen-8-yl]-4-methylbenzamide
  参考文献：
  名称：

  Design, synthesis, and antiproliferative and CDK2-cyclin a inhibitory activity of novel flavopiridol analogues

  摘要：

  The design and synthesis of a small library of 8-amidoflavone, 8-sulfonamidoflavone, 8-amido-7-hydroxyflavone, and heterocyclic analogues of flavopiridol is reported. The potential activity of these compounds as kinase inhibitors was evaluated by cytotoxicity studies in MCF-7 and ID-8 cancer cell lines and inhibition of CDK2-Cyclin A enzyme activity in vitro. The anti-proliferative and CDK2-Cyclin A inhibitory activity of these analogues was significantly lower than the activity of flavopiridol. Molecular docking simulations were carried out and these studies suggested a different binding orientation inside the CDK2 binding pocket for these analogues compared to flavopiridol. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.063
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 、 邻氯苯甲酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 3.0h， 以92%的产率得到2',4',6'-tris(2-chlorobenzoyloxy)acetophenone
  参考文献：
  名称：

  Design, synthesis, and antiproliferative and CDK2-cyclin a inhibitory activity of novel flavopiridol analogues

  摘要：

  The design and synthesis of a small library of 8-amidoflavone, 8-sulfonamidoflavone, 8-amido-7-hydroxyflavone, and heterocyclic analogues of flavopiridol is reported. The potential activity of these compounds as kinase inhibitors was evaluated by cytotoxicity studies in MCF-7 and ID-8 cancer cell lines and inhibition of CDK2-Cyclin A enzyme activity in vitro. The anti-proliferative and CDK2-Cyclin A inhibitory activity of these analogues was significantly lower than the activity of flavopiridol. Molecular docking simulations were carried out and these studies suggested a different binding orientation inside the CDK2 binding pocket for these analogues compared to flavopiridol. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.063