3-sulfo-N-(4-carboxybenzyl)-1,8-naphthalimide potassium salt | 1419321-18-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 3-sulfo-N-(4-carboxybenzyl)-1,8-naphthalimide potassium salt
• 英文别名: Potassium;2-[(4-carboxyphenyl)methyl]-1,3-dioxobenzo[de]isoquinoline-5-sulfonate；potassium;2-[(4-carboxyphenyl)methyl]-1,3-dioxobenzo[de]isoquinoline-5-sulfonate
• CAS: 1419321-18-8
• 化学式: C₂₀H₁₂NO₇S*K
• 分子量: 449.482
• InChiKey: FISLMPLTSDNFPV-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.76
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  131.88
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  1,8-萘二甲酸酐 在 fuming sulfuric acid 作用下， 以 乙醇 、 水 为溶剂， 生成 3-sulfo-N-(4-carboxybenzyl)-1,8-naphthalimide potassium salt
  参考文献：
  名称：

  Development of 1,8-Naphthalimides as Clathrin Inhibitors

  摘要：

  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.

  DOI：

  10.1021/jm4015263

文献信息

• 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.