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2-phthalimidethyl nitrate | 103417-62-5

中文名称
——
中文别名
——
英文名称
2-phthalimidethyl nitrate
英文别名
2-(1,3-Dioxo-1,3-dihydro-2h-isoindol-2-yl)ethyl nitrate;2-(1,3-dioxoisoindol-2-yl)ethyl nitrate
2-phthalimidethyl nitrate化学式
CAS
103417-62-5
化学式
C10H8N2O5
mdl
——
分子量
236.184
InChiKey
ZRJKVZGEPHXMRJ-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    1.8
  • 重原子数:
    17
  • 可旋转键数:
    3
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.2
  • 拓扑面积:
    92.4
  • 氢给体数:
    0
  • 氢受体数:
    5

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    2-phthalimidethyl nitrate乙基苯三正丁基氢锡 作用下, 以 氘代苯 为溶剂, 反应 2.0h, 以100%的产率得到N-羟乙基酞酰亚胺
    参考文献:
    名称:
    Easton, Christopher J.; Ivory, Andrew J.; Smith, Craig A., Journal of the Chemical Society. Perkin Transactions 2 (2001), 1997, # 3, p. 503 - 507
    摘要:
    DOI:
  • 作为产物:
    描述:
    N-羟乙基酞酰亚胺硝酸乙酸酐 作用下, 反应 0.08h, 以65%的产率得到2-phthalimidethyl nitrate
    参考文献:
    名称:
    Easton, Christopher J.; Ivory, Andrew J.; Smith, Craig A., Journal of the Chemical Society. Perkin Transactions 2 (2001), 1997, # 3, p. 503 - 507
    摘要:
    DOI:
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文献信息

  • Practical Method for the Preparation of Nitrate Esters
    作者:Jih Ru Hwu、Kavita A. Vyas、Himatkumar V. Patel、Chun-Hsu Lin、Jen-Chang Yang
    DOI:10.1055/s-1994-25503
    日期:——
    A new and cost-effective method was developed for the preparation of nitrate esters in 67-92 % yields from the corresponding alkyl toluenesulfonates and sodium nitrate with a catalytic amount of tetrabutylammonium nitrate in benzene and water at 110-135°C in a sealed tube.
    本研究开发了一种成本效益高的新方法,可在密封管中于 110-135°C 的温度下,在苯和水中使用催化量的硝酸四丁基铵,从相应的甲苯磺酸烷基酯和硝酸钠制备硝酸酯,收率为 67-92%。
  • Phthalimide derivatives, compositions containing them and a process for preparing them
    申请人:SANKYO COMPANY LIMITED
    公开号:EP0171977A1
    公开(公告)日:1986-02-19
    Compounds of formula (I): (wherein R2 and A are a variety of organic groups, optionally hydroxy- or nitrooxy-substituted, and R1 is hydrogen or nitro) are new compounds valuable in the treatment of ischaemic heart disease, especially angina pectoris. They may be prepared by nitrating the corresponding hydroxy compound.
    式(I)化合物: (其中 R2 和 A 是各种有机基团,可选择羟基或硝基氧基取代,R1 是氢或硝基)是治疗缺血性心脏病,特别是心绞痛很有价值的新化合物。它们可以通过硝化相应的羟基化合物来制备。
  • 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.
  • Activities of 2-phthalimidethanol and 2-phthalimidethyl nitrate, phthalimide analogs devoid of the glutarimide moiety, in experimental models of inflammatory pain and edema
    作者:Adriana M. Godin、Débora P. Araújo、Raquel R. Menezes、Ana Mercy S. Brito、Ivo S.F. Melo、Giovanna M.E. Coura、Darly G. Soares、Leandro F.S. Bastos、Flávio A. Amaral、Lucas S. Ribeiro、Daiane Boff、Julliana R.A. Santos、Daniel A. Santos、Mauro M. Teixeira、Ângelo de Fátima、Renes R. Machado、Márcio M. Coelho
    DOI:10.1016/j.pbb.2014.04.008
    日期:2014.7
    The reintroduction of thalidomide in the pharmacotherapy greatly stimulated the interest in the synthesis and pharmacological evaluation of phthalimide analogs with new and improved activities and also greater safety. In the present study, we evaluated the activities of two phthalimide analogs devoid of the glutarimide ring, namely 2-phthalimidethanol (PTD-OH) and 2-phthalimidethyl nitrate (PTD-NO), in experimental models of inflammatory pain and edema in male C57BL/6J mice. Intraplantar (i.pl.) injection of carrageenan (300 jig) induced mechanical allodynia and this response was inhibited by previous per os (p.o.) administration of PTD-OH and PTD-NO (750 mg/kg) and also by thalidomide (500 or 750 mg/kg). The edema induced by carrageenan was also inhibited by previous p.o. administration of PTD-OH (500 and 750 mg/kg) and PTD-NO (125, 250, 500 or 750 mg/kg), but not by thalidomide. Carrageenan increased tumor necrosis factor (TNF)-alpha and CXCL1 concentrations and also the number of neutrophils in the paw tissue. Previous p.o. administration of PTD-NO (500 mg/kg) reduced all the parameters, while PTD-OH (500 mg/kg) reduced only the accumulation of neutrophils. Thalidomide, on the other hand, was devoid of effect on these biochemical parameters. Plasma concentrations of nitrite were increased after p.o. administration of the phthalimide analog coupled to a NO donor, PTD-NO (500 mg/kg), but not after administration of PTD-OH or thalidomide. In conclusion, our results show that small molecules, structurally much simpler than thalidomide or many of its analogs under investigation, exhibit similar activities in experimental models of pain and inflammation. Finally, as there is evidence that the glutarimide moiety contributes to the teratogenic effect of many thalidomide analogs, our results indicate that phthalimide analogs devoid of this functional group could represent a new class of analgesic and anti-inflammatory candidates with potential greater safety. (C) 2014 Elsevier Inc. All rights reserved.
  • 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.
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