N-nitroxymethyl-phthalimide | 208332-52-9

• 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: N-nitroxymethyl-phthalimide
• 英文别名: (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl nitrate；(1,3-dioxoisoindol-2-yl)methyl nitrate
• CAS: 208332-52-9
• 化学式: C₉H₆N₂O₅
• 分子量: 222.157
• InChiKey: YMLWSLNPDWEKNG-UHFFFAOYSA-N

物化性质

• 熔点：
  75-77 °C
• 沸点：
  364.0±25.0 °C(Predicted)
• 密度：
  1.555±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-nitroxymethyl-phthalimide 在 水 、 hydroxide 作用下， 以 乙腈 为溶剂， 生成 邻氨甲酰苯甲酸
  参考文献：
  名称：

  邻苯二甲酰亚胺甲基作为药物的一部分。探测其反应性。

  摘要：

  邻苯二甲酰亚胺甲基衍生物1，具有广泛的离去基团能力，可通过确定邻苯二甲酰亚胺羰基的速率，迅速水解为相应的邻苯二甲酸。

  DOI：

  10.1016/s0960-894x(98)00135-8
• 作为产物：
  描述：

  N-羟甲基邻苯二甲酰亚胺 在 硝酸 作用下， 反应 0.5h， 以53%的产率得到N-nitroxymethyl-phthalimide
  参考文献：
  名称：

  邻苯二甲酰亚胺甲基作为药物的一部分。探测其反应性。

  摘要：

  邻苯二甲酰亚胺甲基衍生物1，具有广泛的离去基团能力，可通过确定邻苯二甲酰亚胺羰基的速率，迅速水解为相应的邻苯二甲酸。

  DOI：

  10.1016/s0960-894x(98)00135-8

文献信息

• Determination of the Inductive Constant of the Succinimide Group from the Reaction Series of Thermolysis of Nitro Esters
  作者：T. K. Goncharov、V. V. Dubikhin、G. M. Nazin、B. S. Fedorov、A. V. Shastin

  DOI：10.1007/s11176-005-0342-7

  日期：2005.6

  The inductive constant σ* of the succinimide group was determined using the previously obtained equation correlating the rate constant k l ofliquid-phase homolysis of the O-NO2 bond in nitro esters with the σ* constants of electronegative substituents. The kinetics of thermolysis of N-nitroxymethyl- and N-(2-nitroxyethyl)succinimide in the melt and solutions was studied manometrically. Adequate data for k l were obtained. The σ* constant of the succinimide group was determined to be 4.5. The σ* constants for the phthalimide group and some other imide substituents were determined by a similar procedure.

  琥珀酰亚胺基团的感应常数 σ* 是利用之前获得的硝基酯中 O-NO2 键的液相均解速率常数 k l 与电负性取代基的 σ* 常数之间的关系式确定的。通过人工计量法研究了 N-硝基甲基和 N-(2-硝基乙基)琥珀酰亚胺在熔体和溶液中的热解动力学。获得了 k l 的充分数据。琥珀酰亚胺基团的 σ* 常数被确定为 4.5。邻苯二甲酰亚胺基团和其他一些亚胺取代基的 σ* 常数也是通过类似的程序确定的。
• Design, Synthesis, and Pharmacological Evaluation of Novel Hybrid Compounds To Treat Sickle Cell Disease Symptoms
  作者：Jean Leandro dos Santos、Carolina Lanaro、Lídia Moreira Lima、Sheley Gambero、Carla Fernanda Franco-Penteado、Magna Suzana Alexandre-Moreira、Marlene Wade、Shobha Yerigenahally、Abdullah Kutlar、Steffen E. Meiler、Fernando Ferreira Costa、ManChin Chung

  DOI：10.1021/jm200531f

  日期：2011.8.25

  A novel series of thalidomide derivatives (4a-f) designed by molecular hybridization were synthesized and evaluated in vitro and in vivo for their potential use in the oral treatment of sickle cell disease symptoms. Compounds 4a-f demonstrated analgesic, anti-inflammatory, and NO-donor properties. Compounds 4c and 4d were considered promising candidate drugs and were further evaluated in transgenic sickle cell mice to determine their capacity to reduce the levels of the proinflammatory cytokine tumor necrosis factor alpha (TNF alpha). Unlike hydroxyurea, the compounds reduced the concentrations of TNF alpha to levels similar to those induced with the control dexamethasone (300 mu mol/kg). These compounds are novel lead drug candidates with multiple beneficial actions in the treatment of sickle cell disease symptoms and offer an alternative to hydroxyurea treatment.
• USE OF PHTHALIMIDE AND/OR SULPHONAMIDE DERIVATIVES IN THE TREATMENT OF DISEASES WHICH REQUIRE REDUCING THE TNF-alpha LEVELS AND AN EXOGENOUS SOURCE OF NITRIC OXIDE, PHTHALIMIDE DERIVATIVES, SULPHONAMIDE DERIVATIVES, AND A METHOD FOR OBTAINING A SULPHONAMIDE DERIVATIVE
  申请人：Dos Santos Jean Leandro

  公开号：US20100324107A1

  公开（公告）日：2010-12-23

  The present invention refers to the use of phthalimide and/or sulphonamide derivatives with nitric oxide donor properties, which have important activities in increasing the gamma-globin gene expression and anti-inflammatory and analgesic activities, effective in the treatment of hematologic diseases which require reducing the TNF-α levels and an exogenous source of nitric oxide. More particularly, the present invention describes the use of such phthalimide and/or sulphonamide derivatives for the treatment of sickle-cell disease. The invention also has as a novel characteristic the disclosure of new functionalized phthalimide derivatives designed from the prototypes thalidomide and hydroxyurea, and designed rationally through the strategy of molecular hybridization for the treatment of said diseases. The invention still discloses a new method for obtaining a specific sulphonamide derivative which can be used in the preparation of a drug for the treatment of diseases which require reducing the levels of the TNF-α factor and an exogenous source of nitric oxide.
• US8314255B2
  申请人：——

  公开号：US8314255B2

  公开（公告）日：2012-11-20
• US8338474B2
  申请人：——

  公开号：US8338474B2

  公开（公告）日：2012-12-25