2-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl)benzenesulfonic acid | 100330-82-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl)benzenesulfonic acid
• 英文别名: 2-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl) benzenesulfonic acid；2-[2-(2,4-dioxopentan-3-ylidene)hydrazinyl]benzenesulfonic acid
• CAS: 100330-82-3
• 化学式: C₁₁H₁₂N₂O₅S
• 分子量: 284.293
• InChiKey: ZFXRVMTTZLFMDK-UHFFFAOYSA-N

物化性质

• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.88
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  112.9
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl)benzenesulfonic acid 、 copper(II) nitrate trihydrate 在 NH₄OH 作用下， 以 水 为溶剂， 以60%的产率得到
  参考文献：
  名称：

  铜（ii）与3-（邻位取代的苯基肼基）戊烷-2,4-二酮的配合物：环己烷氧化的合成，性质和催化活性†

  摘要：

  铜（II）与3-苯基肼基戊烷-2,4-二酮X-2-C 6 H 4 –NHN C {C（O）CH 3 } 2在邻位带有取代基的反应[X = OH（H 2 L 1）1，AsO 3 H 2（H 3 L 2）2，Cl（HL 3）3，SO 3 H（H 2 L 4）4，COOCH 3（HL 5）5，COOH（H2 L 6） 6，NO 2（HL 7） 7或H（HL 8） 8 ]导致各种络合物，包括单体[CuL 4（H 2 O） 2 ]·H 2 O 10，[CuL 4（ ħ 2 O） 2 ] 11和[铜（HL 4） 2（H 2 O） 4 ] 12，二聚物[Cu 2（H 2 O） 2（μ-HL 2）2 ] 9和聚合物[Cu（μ-L 6）] Ñ ] 13分的，常带有两个稠合的六元metallacycles。配合物10–12可以相互转化，具体取决于pH和温度，而Cu（ II）与4（在存在氰基胍 或者 咪唑（IM），得到单体化合物[铜（H

  DOI：

  10.1039/c0dt01527j
• 作为产物：
  描述：

  2-氨基苯磺酸 、 乙酰丙酮 在 盐酸 、 sodium hydroxide 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.0h， 以75%的产率得到2-(2-(2,4-dioxopentan-3-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

文献信息

• 1D Cu(II) coordination polymer derived from 2-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl)benzenesulfonate chelator and pyrazine spacer
  作者：Kamran T. Mahmudov、Matti Haukka、Manas Sutradhar、Archana Mizar、Maximilian N. Kopylovich、Armando J.L. Pombeiro

  DOI：10.1016/j.molstruc.2012.08.012

  日期：2013.2

  Reaction of 2-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl)benzenesulfonic acid (H2L) with copper(II) nitrate hydrate in the presence of pyrazine (pz) in methanol affords the coordination polymer [Cu-2(mu-L)(2)(H2O)(2)(mu-pz)](n) (1), where the bidentate pz molecule links two Cu(II) centres of two different dimeric units, giving rise to a one-dimensional chain. The dimeric unit [Cu-2(mu-L)(2)(H2O)(2)] consists of two distorted octahedral Cu(II) centres connected via oxygen atoms of the sulfo group of the bridging L2- ligand. The extensive hydrogen bonding between the coordinated water and pz molecules leads to the formation of a supramolecular 3D associate. Compound 1 has been characterized by elemental analysis, ESI-MS, IR spectroscopy and single-crystal X-ray diffraction analysis. Crown Copyright (C) 2012 Published by Elsevier B.V. All rights reserved.