4-methoxy-N-(3-(4-methoxyphenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzamide | 1134320-30-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-methoxy-N-(3-(4-methoxyphenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzamide
• 英文别名: 4-methoxy-N-[3-(4-methoxyphenyl)-1,4-dioxonaphthalen-2-yl]benzamide
• CAS: 1134320-30-1
• 化学式: C₂₅H₁₉NO₅
• 分子量: 413.43
• InChiKey: DREJSHIFZCYEIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-amino-3-(4-methoxyphenyl)naphthalene-1,4-dione 、 对甲氧基苯甲酰氯 在 sodium hydride 作用下， 生成 4-methoxy-N-(3-(4-methoxyphenyl)-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

文献信息

• INHIBITORS OF THE MITF MOLECULAR PATHWAY
  申请人：THE GENERAL HOSPITAL CORPORATION

  公开号：US20160130222A1

  公开（公告）日：2016-05-12

  Provided herein are compounds of the formula (IV) as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful as MITF inhibitors, MITF pathway inhibitors and for the treatment of cancer.

  本文提供的是公式（IV）的化合物及其药学上可接受的盐，其中取代基如规范中所披露的那样。这些化合物及其含有的药物组合物可用作MITF抑制剂、MITF通路抑制剂以及治疗癌症的药物。
• BIOMARKERS PREDICTIVE OF CANCER CELL RESPONSE TO ML329 OR A DERIVATIVE THEREOF
  申请人：Dana-Farber Cancer Institute, Inc.

  公开号：US20220128562A1

  公开（公告）日：2022-04-28

  The present invention is based in part on the identification of biomarkers, including NQO1, NRF2 and KEAP1, predictive of cancer cell responsiveness to treatment with ML 329 or a derivative thereof.
• US9745261B2
  申请人：——

  公开号：US9745261B2

  公开（公告）日：2017-08-29
• [EN] INHIBITORS OF THE MITF MOLECULAR PATHWAY<br/>[FR] INHIBITEURS DE LA VOIE MOLÉCULAIRE MITF
  申请人：GEN HOSPITAL CORP

  公开号：WO2014201016A2

  公开（公告）日：2014-12-18

  Provided herein are compounds of the formula (IV) as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful as MITF inhibitors, MITF pathway inhibitors and for the treatment of cancer.
• 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.