3-sulfo-1,8-naphthalic anhydride sodium salt

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-sulfo-1,8-naphthalic anhydride sodium salt
• 英文别名: Sodium;2,4-dioxo-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaene-7-sulfonate；sodium;2,4-dioxo-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaene-7-sulfonate
• 化学式: C₁₂H₅O₆S*Na
• 分子量: 300.224
• InChiKey: CHCFGIFBJVBNPZ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.94
• 重原子数：
  20
• 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：
  109
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-sulfo-1,8-naphthalic anhydride sodium salt 在 ammonium hydroxide 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 Sodium;2-[(4-boronophenyl)methyl]-1,3-dioxobenzo[de]isoquinoline-5-sulfonate
  参考文献：
  名称：

  具有双重荧光地址的光驱动轮烷分子穿梭分子。

  摘要：

  [反应：见正文]合成了包含α-CD大环，偶氮苯单元和两个不同的荧光萘二甲酰亚胺单元的分子穿梭分子。偶氮苯单元的顺-反光异构化导致CD大环在轨道上运动。由于两个调节器单元的荧光变化易于调节且完全可逆，因此分子穿梭可用作分子存储介质或带有全光输入和输出的开关。

  DOI：

  10.1021/ol049605g
• 作为产物：
  描述：

  1,8-萘二甲酸酐 在 oleum 作用下， 反应 1.0h， 以95.6%的产率得到3-sulfo-1,8-naphthalic anhydride sodium salt
  参考文献：
  名称：

  [EN] INHIBITION OF CLATHRIN
  [FR] INHIBITION DE LA CLATHRINE

  摘要：

  公开号：

  WO2013010218A9

文献信息

• Ionic liquids accelerate access to N-substituted-1,8-naphthalimides
  作者：Kylie A. MacGregor、Adam McCluskey

  DOI：10.1016/j.tetlet.2010.12.015

  日期：2011.2

  The synthesis of N-substituted-1,8-naphthalimides is accelerated in the presence of the room temperature ionic liquid [BMIM][NO(3)]. Reaction times are reduced from 18 h in volatile organic compounds (VOCs) (PhCH(3), EtOH and THF) to 20 min in the ionic liquid [BMIM][NO(3)]. The reaction yields are typically increased to >85% and the products are isolated by ethanol-mediated precipitation direct from the ionic liquid, requiring no further purification. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.
• Development of 1,8-Naphthalimides as Clathrin Inhibitors
  作者：Kylie A. MacGregor、Mark J. Robertson、Kelly A. Young、Lisa von Kleist、Wiebke Stahlschmidt、Ainslie Whiting、Ngoc Chau、Phillip J. Robinson、Volker Haucke、Adam McCluskey

  DOI：10.1021/jm4015263

  日期：2014.1.9

  We reported the first small molecule inhibitors of the interaction between the clathrin N-terminal domain (TD) and endocyctic accessory proteins (i.e., clathrin inhibition(1)). Initial screening of a similar to 17 000 small molecule ChemBioNet library identified 1. Screening of an existing in-house propriety library identified four substituted 1,8-napthalimides as similar to 80-120 mu M clathrin inhibitors. Focused library development gave 3-sulfo-N-(4-aminobenzyl)-1,8-naphthalimide, potassium salt (18, IC50 approximate to 18 mu M). A second library targeting the 4-aminobenzyl moiety was developed, and four anogues displayed comparable activity (26, 27, 28, 34 with IC50 values of 22, 16, 15, and 15 mu M respectively) with a further four (24, 25, 32, 33) more active than 18 with IC50 values of 10, 6.9, 12, and 10 mu M, respectively. Docking studies rationalized the structure activity relationship (SAR) with the biological data. 3-Sulfo-N-benzyl-1,8-naphthalimide, potassium salt (25) with an IC50 approximate to 6.9 mu M, is the most potent clathrin terminal domain-amphiphysin inhibitor reported to date.
• [EN] INHIBITION OF CLATHRIN<br/>[FR] INHIBITION DE LA CLATHRINE
  申请人：UNIV BERLIN FREIE

  公开号：WO2013010218A9

  公开（公告）日：2013-03-28
• A Light-Driven Rotaxane Molecular Shuttle with Dual Fluorescence Addresses
  作者：Da-Hui Qu、Qiao-Chun Wang、Jun Ren、He Tian

  DOI：10.1021/ol049605g

  日期：2004.6.1

  see text] A molecular shuttle containing an alpha-CD macrocycle, an azobenzene unit, and two different fluorescent naphthalimide units was synthesized. The cis-trans photoisomerization of the azobenzene unit resulted in the motion of the CD macrocycle on the track. Because of the easy regulation and full reversibility of the fluorescence change of the two stopper units, the molecular shuttle could be

  [反应：见正文]合成了包含α-CD大环，偶氮苯单元和两个不同的荧光萘二甲酰亚胺单元的分子穿梭分子。偶氮苯单元的顺-反光异构化导致CD大环在轨道上运动。由于两个调节器单元的荧光变化易于调节且完全可逆，因此分子穿梭可用作分子存储介质或带有全光输入和输出的开关。