2-(2-chlorophenyl)-8-(4-chlorophenylamino)-5-hydroxy-4-oxo-4H-chromen-7-yl 4-chlorobenzoate | 920006-44-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(2-chlorophenyl)-8-(4-chlorophenylamino)-5-hydroxy-4-oxo-4H-chromen-7-yl 4-chlorobenzoate
• 英文别名: [8-[(4-Chlorobenzoyl)amino]-2-(2-chlorophenyl)-5-hydroxy-4-oxochromen-7-yl] 4-chlorobenzoate
• CAS: 920006-44-6
• 化学式: C₂₉H₁₆Cl₃NO₆
• 分子量: 580.808
• InChiKey: RPMYPSUPMYEIIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2-chlorophenyl)-8-(4-chlorophenylamino)-5-hydroxy-4-oxo-4H-chromen-7-yl 4-chlorobenzoate 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 0.25h， 以20 mg的产率得到4-chloro-N-[2-(2-chlorophenyl)-5,7-dihydroxy-4-oxo-4H-chromen-8-yl]benzamide
  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 在 吡啶 、 4-二甲氨基吡啶 、 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 为溶剂， 反应 14.17h， 生成 2-(2-chlorophenyl)-8-(4-chlorophenylamino)-5-hydroxy-4-oxo-4H-chromen-7-yl 4-chlorobenzoate
  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

文献信息

• Design, synthesis, and antiproliferative and CDK2-cyclin a inhibitory activity of novel flavopiridol analogues
  作者：Yu Mi Ahn、Lakshminarayana Vogeti、Chun-Jing Liu、Hari K.R. Santhapuram、Jonathan M. White、Veena Vasandani、Lester A. Mitscher、Gerald H. Lushington、Paul R. Hanson、Douglas R. Powell、Richard H. Himes、Katherine F. Roby、Qizhuang Ye、Gunda I. Georg

  DOI：10.1016/j.bmc.2006.10.063

  日期：2007.1

  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.