2-Amino-3-(3-chlorophenyl)naphthalene-1,4-dione | 1134319-92-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Amino-3-(3-chlorophenyl)naphthalene-1,4-dione
• 英文别名: 2-amino-3-(3-chlorophenyl)naphthalene-1,4-dione
• CAS: 1134319-92-8
• 化学式: C₁₆H₁₀ClNO₂
• 分子量: 283.714
• InChiKey: LWMYDKVPHFMJQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Amino-3-(3-chlorophenyl)naphthalene-1,4-dione 、 苯甲酰氯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 N-[3-(3-chlorophenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl]benzamide
  参考文献：
  名称：

  Synthesis and evaluation of Hsp90 inhibitors that contain the 1,4-naphthoquinone scaffold

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2008.11.064
• 作为产物：
  描述：

  2-氨基-3-氯-1,4-萘醌 、 3-氯苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2-Amino-3-(3-chlorophenyl)naphthalene-1,4-dione
  参考文献：
  名称：

  Synthesis and evaluation of Hsp90 inhibitors that contain the 1,4-naphthoquinone scaffold

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2008.11.064

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.