3,8-dinitro-phenanthridin-6-ol | 23818-38-4

• 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-dinitro-phenanthridin-6-ol
• 英文别名: 3,8-dinitrophenanthridin-6(5H)-one；3,8-dinitro-5H-phenanthridin-6-one
• CAS: 23818-38-4
• 化学式: C₁₃H₇N₃O₅
• 分子量: 285.216
• InChiKey: NFQCBMOTZZLRCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,7-二硝基-9-芴酮 在 sodium azide 、 硫酸 、 水 作用下， 生成 3,8-dinitro-phenanthridin-6-ol
  参考文献：
  名称：

  Arcus et al., Journal of the Chemical Society, 1956, p. 1498,1506

  摘要：

  DOI：

文献信息

• One-Pot Preparation of (<i>NH</i>)-Phenanthridinones and Amide-Functionalized [7]Helicene-like Molecules from Biaryl Dicarboxylic Acids
  作者：Takuya Murai、Yongning Xing、Mayu Kurokawa、Toshifumi Kuribayashi、Masanori Nikaido、Elghareeb E. Elboray、Shohei Hamada、Yusuke Kobayashi、Takahiro Sasamori、Takeo Kawabata、Takumi Furuta

  DOI：10.1021/acs.joc.1c02769

  日期：2022.5.6

  A one-pot transformation of biaryl dicarboxylic acids to (NH)-phenanthridinone derivatives based on a Curtius rearrangement and subsequent basic hydrolysis was developed. This method is also applicable for the preparation of optically active amide-functionalized [7]helicene-like molecules. Furthermore, aza[5]helicene derivatives with a phosphate moiety were isolated as a product of the Curtius rearrangement

  开发了基于 Curtius 重排和随后的碱性水解的联芳基二羧酸向 ( NH )-菲啶酮衍生物的一锅法转化。该方法也适用于光学活性酰胺官能化[7]类螺烯分子的制备。此外，在带有硫属元素原子的底物的情况下，具有磷酸盐部分的氮杂[5]螺烯衍生物被分离为 Curtius 重排步骤的产物。通过 X 射线衍射分析揭示了这些产品的立体结构，表明硫属元素键合和磷元素键合相互作用可能有助于它们的稳定性。进一步研究了类螺烯分子的构型稳定性及其手性。
• Arcus et al., Journal of the Chemical Society, 1956, p. 1498,1506
  作者：Arcus et al.

  DOI：——

  日期：——
• 337. Researches in the phenanthridine series. Part IV. Synthesis of plasmoquin-like derivatives
  作者：Leslie P. Walls

  DOI：10.1039/jr9350001405

  日期：——
• 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.