2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N'-(4-hydroxy-3-methoxybenzylidene)acetohydrazide | 477515-44-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N'-(4-hydroxy-3-methoxybenzylidene)acetohydrazide
• CAS: 477515-44-9
• 化学式: C₁₈H₁₅N₃O₅
• 分子量: 353.334
• InChiKey: SQEDGZBHDGTUPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  108.3
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N'-(4-hydroxy-3-methoxybenzylidene)acetohydrazide 、 巯基乙酸 在 zinc(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以92%的产率得到2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-N-[2-(4-hydroxy-3-methoxyphenyl)-4-oxothiazolidin-3-yl]acetamide
  参考文献：
  名称：

  Design and synthesis of 2-(1, 3-dioxoisoindolin-2-yl)-N-(4-oxo-2-substitutedthiazolidin-3-yl) acetamide derivatives as potential anticonvulsant agents

  摘要：

  A series of 2-(1,3-dioxoisoindolin-2-yl)-N-(4-oxo-2-substitutedthiazolidin-3-yl) acetamide derivatives were designed and synthesized using appropriate synthetic route, keeping in view the structural requirement of pharmacophore and evaluated for anticonvulsant activity and CNS depressant activities in mice. The synthesized derivatives were examined in the maximal electroshock seizure (MES), subcutaneous pentylenetetrazole (sc-PTZ) induced seizure and neurotoxicity screens and were also evaluated for behavioral activity. All the tested compounds showed protection against MES test indicative of their ability to inhibit the seizure spread. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.003
• 作为产物：
  描述：

  邻苯二甲酰甘氨酸 在 氯化亚砜 、 溶剂黄146 、 肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 6.0h， 生成 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N'-(4-hydroxy-3-methoxybenzylidene)acetohydrazide
  参考文献：
  名称：

  Synthesis, characterization, and computational studies on phthalic anhydride-based benzylidene-hydrazide derivatives as novel, potential anti-inflammatory agents

  摘要：

  A series of phthalic anhydride-based substituted benzylidene-hydrazide derivatives (3a-i) was synthesized. The synthesized derivatives were authenticated by TLC, UV-visible, FTIR, NMR, and mass spectroscopic techniques and further screened for in vivo anti-inflammatory and analgesic activities by carrageenan-induced rat paw oedema and tail immersion methods, respectively, using diclofenac sodium as standard drug. The derivatives 3d, 3e, and 3h were found to be most active anti-inflammatory and analgesic agents among all the synthesized derivatives. The physico-chemical similarity of the derivatives with standard drugs was assessed by calculating various physicochemical properties using software programs. The percent similarity of synthesized derivatives was found to be good except 3i. The derivatives were subjected to QSAR by multilinear regression using Analyze it version 3.0 software and two statistically sound models were developed with R (2) (0.933-0.960), (0.595-0.762) and Q (2) (0.999) with good F (2.76-4.84) values. Molecular docking studies were performed by MVD software (version 2012.5.0.0). The derivative 3h has emerged out as most potent anti-inflammatory agent with highest dock score, i.e., -93.64.

  DOI：

  10.1007/s00044-013-0848-1