2-hydroxy-5-nitro-3-(2-(2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)hydrazinyl)benzenesulfonic acid | 1389396-43-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-hydroxy-5-nitro-3-(2-(2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)hydrazinyl)benzenesulfonic acid
• 英文别名: 2-hydroxy-5-nitro-3-[2-(2,4,6-trioxo-1,3-diazinan-5-ylidene)hydrazinyl]benzenesulfonic acid
• CAS: 1389396-43-3
• 化学式: C₁₀H₇N₅O₉S
• 分子量: 373.26
• InChiKey: DVSDDDGJFMMYBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.32
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  217.4
• 氢给体数：
  5.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  sodium hydroxide 、 水 、 copper(II) nitrate 、 2-hydroxy-5-nitro-3-(2-(2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)hydrazinyl)benzenesulfonic acid 以 水 为溶剂， 以48%的产率得到[CuNa(H2O)2(η9-2-hydroxy-5-nitro-3-(2-(2,4,6-trioxatetrahydropyrimidin-5(2H)ylidene)hydrazinyl)benzene sulfonic acid(-3H))]..
  参考文献：
  名称：

  包含巴比妥酸的芳基腙作为配体的水溶性异金属铜(II)-钠络合物

  摘要：

  摘要 一种新的水溶性 CuII-Na 配位聚合物 {[Cu(H2O)Na(H2O)(η9-L)]·2H2O}n，可以通过硝酸铜 (II)、氢氧化钠和2-羟基-5-硝基-3-(2-(2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)hydrazinyl)benzo sulfonic acid (H3L) 一种新型水溶性巴比妥酸芳基腙。该配合物通过红外光谱、元素和单晶 X 射线衍射分析进行表征，揭示了由完全去质子化的 L3-衍生物与五种金属阳离子（三个 NaI 和两个 CuII ）。这些链插入了结晶水分子，通过广泛的氢键相互作用使结构扩展到 3D。

  DOI：

  10.1016/j.inoche.2012.06.008
• 作为产物：
  描述：

  巴比妥酸 、 2-氨基-4-硝基苯酚-6-磺酸 在 盐酸 、 sodium hydroxide 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.0h， 以65%的产率得到2-hydroxy-5-nitro-3-(2-(2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)hydrazinyl)benzenesulfonic acid
  参考文献：
  名称：

  2-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl)benzonitrile as novel inhibitor of receptor tyrosine kinase and PI3K/AKT/mTOR signaling pathway in glioblastoma

  摘要：

  Nerve growth factor receptor (NGFR), a member of kinase protein, is emerging as an important target for Glioblastoma (GBM) treatment. Overexpression of NGFR is observed in many metastatic cancers including GBM, promoting tumor migration and invasion. Hydrazones have been reported to effectively interact with receptor tyrosine kinases (RTKs). We report herein the synthesis of 23 arylhydrazones of active methylene compounds (AHAMCs) compounds and their anti-proliferative activity against GBM cell lines, LN229 and U87. Compound 8234, 2-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl)benzonitrile, was identified as the most active anti-neoplastic compound, with the IC50 value ranging 87 mu M - 107 mu M Molecular docking simulations of the synthesized compounds into the active site of tyrosine receptor kinase A (TrkA), demonstrated a strong binding affinity with 8234 and concurs well with the obtained biological results. 8234 was found to be a negative regulator of PI3K/Akt/mTOR pathway and an enhancer of p53 expression. In addition, 8234 treated GBM cells exhibited the downregulation of cyclins, cyclin-dependent kinases and other key molecules involved in cell cycle such as CCNE, E2F, CCND, CDK6, indicating that 8234 induces cell cycle arrest at G1/S. R234 also exerted its apoptotic effects independent of caspase3/7 activity, in both cell lines. In U87 cells, 8234 induced oxidative effects whereas LN229 cells annulled oxidative stress. The study thus concludes that 8234, being a negative modulator of RTKs and cell cycle inhibitor, may represent a novel class of anti-GBM drugs. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.01.021