5-nitro-2-(1,3-thiazol-2-yl)-1H-isoindole-1,3(2H)-dione | 302927-83-9

• 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: 5-nitro-2-(1,3-thiazol-2-yl)-1H-isoindole-1,3(2H)-dione
• 英文别名: 4-Nitro-N-(2-thiazolyl)phthalimide；5-nitro-2-(1,3-thiazol-2-yl)isoindole-1,3-dione
• CAS: 302927-83-9
• 化学式: C₁₁H₅N₃O₄S
• mdl: MFCD00425076
• 分子量: 275.244
• InChiKey: AZBFJMQLIITNQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氨基噻唑 、 4-硝基邻苯二甲酸酐 在 溶剂黄146 作用下， 反应 18.0h， 以45%的产率得到5-nitro-2-(1,3-thiazol-2-yl)-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Design, Synthesis and Protection Against Pentylenetetrazole-induced Seizure of N-aryl Derivatives of the Phthalimide Pharmacophore

  摘要：

  A series of compounds including N-aryl substituents of phthalimide and 4-nitrophthalimide were synthesized and evaluated for their anticonvulsant properties. The in vivo screening data suggest that all the analogs have the ability to protect against pentylenetetrazole-induced seizures. These compounds exerted their maximal effects 30 min after administration. The most potent compound in both, tonic and clonic seizure was 1-naphthyl derivative (comp. 6), which was more active than the reference drug known as Phenytoin. Using an open pore model of the Na channel, these anticonvulsants were docked in the active site and examined in relation to the residues identified by mutagenesis as important for their binding energies. Docking studies revealed that all compounds (1-13) interacted mainly with residues II-S6 of NaV1.2 by making hydrogen bonds and additional hydrophobic interactions with domain I and II in the channel's inner pore.

  DOI：

  10.2174/157340612802084289

文献信息

• Design, Synthesis and Protection Against Pentylenetetrazole-induced Seizure of N-aryl Derivatives of the Phthalimide Pharmacophore
  作者：Asghar Davood、Hamed Shafaroodi、Mohsen Amini、Alireza Nematollahi、Mehrshad Shirazi、Maryam Iman

  DOI：10.2174/157340612802084289

  日期：2012.9.1

  A series of compounds including N-aryl substituents of phthalimide and 4-nitrophthalimide were synthesized and evaluated for their anticonvulsant properties. The in vivo screening data suggest that all the analogs have the ability to protect against pentylenetetrazole-induced seizures. These compounds exerted their maximal effects 30 min after administration. The most potent compound in both, tonic and clonic seizure was 1-naphthyl derivative (comp. 6), which was more active than the reference drug known as Phenytoin. Using an open pore model of the Na channel, these anticonvulsants were docked in the active site and examined in relation to the residues identified by mutagenesis as important for their binding energies. Docking studies revealed that all compounds (1-13) interacted mainly with residues II-S6 of NaV1.2 by making hydrogen bonds and additional hydrophobic interactions with domain I and II in the channel's inner pore.