3-[(phenylamino)methylene]quinoline-2,4(1H,3H)-dione | 59856-27-8

• 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-[(phenylamino)methylene]quinoline-2,4(1H,3H)-dione
• 英文别名: 3-phenylaminomethylenequinoline-2,4-dione；3-anilinomethylene-1H-quinoline-2,4-dione；3-Anilinomethyl-2,4-dioxo-1,2,3,4-tetrahydrochinolin；3-(anilinomethylidene)-1H-quinoline-2,4-dione
• CAS: 59856-27-8
• 化学式: C₁₆H₁₂N₂O₂
• 分子量: 264.283
• InChiKey: OPRCAIYSBBFTJE-UHFFFAOYSA-N

物化性质

• 熔点：
  267 °C
• 沸点：
  492.4±45.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-[(phenylamino)methylene]quinoline-2,4(1H,3H)-dione 在 sodium hydroxide 、 三氯氧磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 14.0h， 生成 2,4-dichloro-3-dichloromethyl-quinoline
  参考文献：
  名称：

  Nucleophilic Chlorination of 3-Formyl-4-hydroxy-quinolin-2(1H)-ones

  摘要：

  Chlorination of 1-substituted 3-formyl-4-hydroxy-2-quinolones (1a, b) with phosphorylchloride leads to 4-chloro-3-dichloromethylquinolones (2), which can be hydrolyzed to 4-chloro-3-formylquinolones (4). From the anilinomethylene quinolinediones (3), at low temperatures the formylquinolones 4 can be obtained directly, whereas at high temperatures cleavage of the tautomeric azomethine moiety followed by subsequent ring closure to the naphthyridines (7) takes place. With 1-unsubstituted 3-formyl-4-hydroxy-2-quinolones (1d) either the 3-dichloromethylquinolone (2d) or the 2,4-dichloro-3-dichloromethylquinoline (10) is obtained depending on the reaction conditions. Similar results are obtained with the 1-unsubstituted anilinomethylene compounds (3). Attempts to obtain the 3-formyl-2,4-dichloroquinoline (11) were unsuccessful because in all experiments the 2-chloro-group was converted to an oxygen function.

  DOI：

  10.1002/prac.19933350203
• 作为产物：
  描述：

  N,N'-二(苯基)丙二酰胺 在 polyphosphoric acid 作用下， 以 乙二醇二甲醚 为溶剂， 反应 8.5h， 生成 3-[(phenylamino)methylene]quinoline-2,4(1H,3H)-dione
  参考文献：
  名称：

  一种杀菌剂中间体的合成方法

  摘要：

  本发明公开了一种杀菌剂中间体的合成方法，包括以下步骤：将丙二酸二乙酯加入一定量的苯胺中氨解，氨解后得到的N1,N3‑二苯基丙二酰胺加入多聚磷酸中环合，反应完毕后精制得到4‑羟基喹啉‑2(1H)‑酮经过胺甲基化反应后得到3‑[(苯基氨基)亚甲基]‑喹啉‑2,4(1H,3H)‑二酮，3‑[(苯基氨基)亚甲基]‑喹啉‑2,4(1H,3H)‑二酮经过氯化水解得到粗品，再经过甲苯打浆即得；本发明原料易得且成本廉价，操作简单，收率高，适合企业化生产。

  公开号：

  CN110642783A

文献信息

• Synthesis and antitumor activity of novel amsacrine analogs: The critical role of the acridine moiety in determining their biological activity
  作者：Adriana Chilin、Giovanni Marzaro、Christine Marzano、Lisa Dalla Via、Maria Grazia Ferlin、Giovanni Pastorini、Adriano Guiotto

  DOI：10.1016/j.bmc.2008.11.072

  日期：2009.1

  A new series of N-[4-(2'-oxo-2H-pyrano[2,3-b]quinolin-5'-ylamino)-phenyl]-methanesulfonamides was prepared and analyzed as novel amsacrine-like derivatives. Our preliminary biological evaluation has shown that the replacement of the acridine moiety with the analogous 2-oxo-2H-pyrano[2,3-b]quinoline system drastically reduced both their anticancer activity and their propency to intercalate into double stranded DNA. (C) 2008 Elsevier Ltd. All rights reserved.
• Discovery of thienoquinolone derivatives as selective and ATP non-competitive CDK5/p25 inhibitors by structure-based virtual screening
  作者：Arindam Chatterjee、Stephen J. Cutler、Robert J. Doerksen、Ikhlas A. Khan、John S. Williamson

  DOI：10.1016/j.bmc.2014.09.043

  日期：2014.11

  Calpain mediated cleavage of CDK5 natural precursor p35 causes a stable complex formation of CDK5/p25, which leads to hyperphosphorylation of tau. Thus inhibition of this complex is a viable target for numerous acute and chronic neurodegenerative diseases involving tau protein, including Alzheimer's disease. Since CDK5 has the highest sequence homology with its mitotic counterpart CDK2, our primary goal was to design selective CDK5/p25 inhibitors targeting neurodegeneration. A novel structure-based virtual screening protocol comprised of e-pharmacophore models and virtual screening workflow was used to identify nine compounds from a commercial database containing 2.84 million compounds. An ATP non-competitive and selective thieno[ 3,2-c] quinolin-4(5H)-one inhibitor (10) with ligand efficiency (LE) of 0.3 was identified as the lead molecule. Further SAR optimization led to the discovery of several low micromolar inhibitors with good selectivity. The research represents a new class of potent ATP noncompetitive CDK5/p25 inhibitors with good CDK2/E selectivity. Published by Elsevier Ltd.