N-[3-(2-chlorophenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl]benzamide | 1134320-13-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[3-(2-chlorophenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl]benzamide
• 英文别名: N-[3-(2-chlorophenyl)-1,4-dioxonaphthalen-2-yl]benzamide
• CAS: 1134320-13-0
• 化学式: C₂₃H₁₄ClNO₃
• 分子量: 387.822
• InChiKey: FGBYQIBOTCYEDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲羟肟酸 、 2-(2-chlorophenyl)naphthalene-1,4-dione 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以36%的产率得到N-[3-(2-chlorophenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl]benzamide
  参考文献：
  名称：

  使用异羟肟酸作为酰胺的萘醌的无金属直接酰胺化：在HDAC6抑制剂的合成中的应用

  摘要：

  开发了一种在碱性条件下萘醌与异羟肟酸反应合成酰胺基醌的新方法。该反应温和且操作简单，并提供了高产率的酰胺基醌。通过这种新方法，成功合成了一种新型的非常强的HDAC6抑制剂，该抑制剂对AML细胞显示出高毒性。

  DOI：

  10.1021/acs.orglett.6b02740

文献信息

• Synthesis and evaluation of Hsp90 inhibitors that contain the 1,4-naphthoquinone scaffold
  作者：M. Kyle Hadden、Stephanie A. Hill、Jason Davenport、Robert L. Matts、Brian S.J. Blagg

  DOI：10.1016/j.bmc.2008.11.064

  日期：2009.1

  High-throughput screening of a library of diverse molecules has identified the 1,4-naphthoquinone scaffold as a new class of Hsp90 inhibitors. The synthesis and evaluation of a rationally-designed series of analogues containing the naphthoquinone core scaffold has provided key structure-activity relationships for these compounds. The most active inhibitors exhibited potent in vitro activity with low micromolar IC50 values in anti-proliferation and Her2 degradation assays. In addition, 3g, 12, and 13a induced the degradation of oncogenic Hsp90 client proteins, a hallmark of Hsp90 inhibition. The identification of these naphthoquinones as Hsp90 inhibitors provides a new scaffold upon which improved Hsp90 inhibitors can be developed. (C) 2008 Elsevier Ltd. All rights reserved.
• Metal-Free Direct Amidation of Naphthoquinones Using Hydroxamic Acids as an Amide Source: Application in the Synthesis of an HDAC6 Inhibitor
  作者：Cheng Zhang、C. James Chou

  DOI：10.1021/acs.orglett.6b02740

  日期：2016.11.4

  A novel synthetic approach to amidoquinones by the reaction of naphthoquinones with hydroxamic acids under basic conditions was developed. The reaction is mild and operationally simple, and it affords high yields of amidoquinones. With this new method, a novel, very strong HDAC6 inhibitor, which showed high toxicity to AML cells, was successfully synthesized.

  开发了一种在碱性条件下萘醌与异羟肟酸反应合成酰胺基醌的新方法。该反应温和且操作简单，并提供了高产率的酰胺基醌。通过这种新方法，成功合成了一种新型的非常强的HDAC6抑制剂，该抑制剂对AML细胞显示出高毒性。