3-[8-fluoro-6(5h)phenanthridinone]carboxylic acid | 376609-14-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-[8-fluoro-6(5h)phenanthridinone]carboxylic acid
• 英文别名: 8-fluoro-6-oxo-5H-phenanthridine-3-carboxylic acid
• CAS: 376609-14-2
• 化学式: C₁₄H₈FNO₃
• 分子量: 257.221
• InChiKey: CLCVKYYVZUKNJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 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：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-苯乙胺 、 3-[8-fluoro-6(5h)phenanthridinone]carboxylic acid 在 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 8-Fluoro-6-oxo-5,6-dihydro-phenanthridine-3-carboxylic acid phenethyl-amide
  参考文献：
  名称：

  Synthesis of substituted 5[H]phenanthridin-6-ones as potent poly(ADP-ribose)polymerase-1 (PARP1) inhibitors

  摘要：

  1-, 2-, 3-, 4-, 8-, or 10-Substituted 5(H)phenanthridin-6-ones were synthesized and found to be potent PARP1 inhibitors. Among the 28 compounds prepared. some showed not only low IC50 values (compound 1b, 10 nM) but also desirable water solubility characteristics. These properties, which are superior to the common PARP1 inhibitors such as benzamides and isoquinolin-1-ones, are essential for potential therapeutic usage. The variety of compounds allows SAR analysis of favored substituents and substituted positions on 5(H)phenanthridin-6-one ring. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00281-5
• 作为产物：
  描述：

  4-碘-3-硝基苯甲酸甲酯 在 sodium hydroxide 、 镍 、 铜 、 肼 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 3-[8-fluoro-6(5h)phenanthridinone]carboxylic acid
  参考文献：
  名称：

  Synthesis of substituted 5[H]phenanthridin-6-ones as potent poly(ADP-ribose)polymerase-1 (PARP1) inhibitors

  摘要：

  1-, 2-, 3-, 4-, 8-, or 10-Substituted 5(H)phenanthridin-6-ones were synthesized and found to be potent PARP1 inhibitors. Among the 28 compounds prepared. some showed not only low IC50 values (compound 1b, 10 nM) but also desirable water solubility characteristics. These properties, which are superior to the common PARP1 inhibitors such as benzamides and isoquinolin-1-ones, are essential for potential therapeutic usage. The variety of compounds allows SAR analysis of favored substituents and substituted positions on 5(H)phenanthridin-6-one ring. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00281-5

文献信息

• Synthesis of substituted 5[H]phenanthridin-6-ones as potent poly(ADP-ribose)polymerase-1 (PARP1) inhibitors
  作者：Jia-He Li、Larisa Serdyuk、Dana V. Ferraris、Ge Xiao、Kevin L. Tays、Paul W. Kletzly、Weixing Li、Susan Lautar、Jie Zhang、Vincent J. Kalish

  DOI：10.1016/s0960-894x(01)00281-5

  日期：2001.7

  1-, 2-, 3-, 4-, 8-, or 10-Substituted 5(H)phenanthridin-6-ones were synthesized and found to be potent PARP1 inhibitors. Among the 28 compounds prepared. some showed not only low IC50 values (compound 1b, 10 nM) but also desirable water solubility characteristics. These properties, which are superior to the common PARP1 inhibitors such as benzamides and isoquinolin-1-ones, are essential for potential therapeutic usage. The variety of compounds allows SAR analysis of favored substituents and substituted positions on 5(H)phenanthridin-6-one ring. (C) 2001 Elsevier Science Ltd. All rights reserved.