(e)-N'-(4-carboxybenzylidene)-2-naphthohydrazide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (e)-N'-(4-carboxybenzylidene)-2-naphthohydrazide
• 英文别名: 4-[(E)-(naphthalene-2-carbonylhydrazinylidene)methyl]benzoic acid
• 化学式: C₁₉H₁₄N₂O₃
• 分子量: 318.332
• InChiKey: ATERQKXYCBXUOY-UDWIEESQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-萘甲酸甲酯 在 盐酸 、 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 1.17h， 生成 (e)-N'-(4-carboxybenzylidene)-2-naphthohydrazide
  参考文献：
  名称：

  Structure-based design and biological profile of (E)-N-(4-Nitrobenzylidene)-2-naphthohydrazide, a novel small molecule inhibitor of IκB kinase-β

  摘要：

  In this study, we describe the rational design, molecular modeling and pharmacological profile of a novel IKK-beta inhibitor (E)-N-(4-nitrobenzylidene)-2-naphthohydrazide (LASSBio-1524). The design based on the IKK-beta active site, and a privileged structure template yielded a novel IKK-beta inhibitor scaffold with significant selectivity over IKK-alpha and CHK2, as assessed by an in vitro kinase assay. For a better understanding of the structural requirements of IKK-beta inhibition, molecular dynamics simulations of LASSBio-1524 (3) were performed. The NAH derivative LASSBio-1524 (3), was able to suppress arachidonic acid-induced edema formation in a dose-dependent manner, demonstrating an in vivo anti-inflammatory effect. The molecular architecture of this novel, low-molecular weight IKK-beta inhibitor is encouraging for further lead optimization toward the development of innovative anti-inflammatory drug candidates. (c) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.045

文献信息

• Structure-based design and biological profile of (E)-N-(4-Nitrobenzylidene)-2-naphthohydrazide, a novel small molecule inhibitor of IκB kinase-β
  作者：Carolina M. Avila、Alexandra B. Lopes、Arlan S. Gonçalves、Leandro L. da Silva、Nelilma C. Romeiro、Ana Luisa P. Miranda、Carlos M.R. Sant’Anna、Eliezer J. Barreiro、Carlos A.M. Fraga

  DOI：10.1016/j.ejmech.2011.01.045

  日期：2011.4

  In this study, we describe the rational design, molecular modeling and pharmacological profile of a novel IKK-beta inhibitor (E)-N-(4-nitrobenzylidene)-2-naphthohydrazide (LASSBio-1524). The design based on the IKK-beta active site, and a privileged structure template yielded a novel IKK-beta inhibitor scaffold with significant selectivity over IKK-alpha and CHK2, as assessed by an in vitro kinase assay. For a better understanding of the structural requirements of IKK-beta inhibition, molecular dynamics simulations of LASSBio-1524 (3) were performed. The NAH derivative LASSBio-1524 (3), was able to suppress arachidonic acid-induced edema formation in a dose-dependent manner, demonstrating an in vivo anti-inflammatory effect. The molecular architecture of this novel, low-molecular weight IKK-beta inhibitor is encouraging for further lead optimization toward the development of innovative anti-inflammatory drug candidates. (c) 2011 Elsevier Masson SAS. All rights reserved.