ethyl 4-(4-((3,4-dihydroisoquinolin-2(1H)-yl)methyl)benzamido)benzoate | 329741-12-0

• 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: ethyl 4-(4-((3,4-dihydroisoquinolin-2(1H)-yl)methyl)benzamido)benzoate
• 英文别名: ethyl 4-[[4-(3,4-dihydro-1H-isoquinolin-2-ylmethyl)benzoyl]amino]benzoate
• CAS: 329741-12-0
• 化学式: C₂₆H₂₆N₂O₃
• mdl: MFCD01167905
• 分子量: 414.504
• InChiKey: PFNLTXPEWXUGPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  四氢异喹啉 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 ethyl 4-(4-((3,4-dihydroisoquinolin-2(1H)-yl)methyl)benzamido)benzoate
  参考文献：
  名称：

  Identification of Inhibitors of NOD1-Induced Nuclear Factor-κB Activation

  摘要：

  NOD1 (nucleotide-binding oligomerization domain 1) protein is a member of the NLR (NACHT and leucine rich repeat domain containing proteins) protein family, which plays a key role in innate immunity as a sensor of specific microbial components derived from bacterial peptidoglycans and induction of inflammatory responses. Mutations in NOD proteins have been associated with various inflammatory diseases that affect NF-kappa B (nuclear factor kappa B) activity, a major signaling pathway involved in apoptosis, inflammation, and immune response. A luciferase-based reporter gene assay was utilized in a high-throughput screening program conducted under the NIH-sponsored Molecular Libraries Probe Production Center Network program to identify the active scaffolds. Herein, we report the chemical synthesis, structure-activity relationship studies, downstream counterscreens, secondary assay data, and pharmacological profiling of the 2-aminobenzimidazole lead (compound 1c, ML130) as a potent and selective inhibitor of NOD 1-induced NF-kappa B activation.

  DOI：

  10.1021/ml200158b

文献信息

• Identification of Inhibitors of NOD1-Induced Nuclear Factor-κB Activation
  作者：Pasha M. Khan、Ricardo G. Correa、Daniela B. Divlianska、Satyamaheshwar Peddibhotla、E. Hampton Sessions、Gavin Magnuson、Brock Brown、Eigo Suyama、Hongbin Yuan、Arianna Mangravita-Novo、Michael Vicchiarelli、Ying Su、Stefan Vasile、Layton H. Smith、Paul W. Diaz、John C. Reed、Gregory P. Roth

  DOI：10.1021/ml200158b

  日期：2011.10.13

  NOD1 (nucleotide-binding oligomerization domain 1) protein is a member of the NLR (NACHT and leucine rich repeat domain containing proteins) protein family, which plays a key role in innate immunity as a sensor of specific microbial components derived from bacterial peptidoglycans and induction of inflammatory responses. Mutations in NOD proteins have been associated with various inflammatory diseases that affect NF-kappa B (nuclear factor kappa B) activity, a major signaling pathway involved in apoptosis, inflammation, and immune response. A luciferase-based reporter gene assay was utilized in a high-throughput screening program conducted under the NIH-sponsored Molecular Libraries Probe Production Center Network program to identify the active scaffolds. Herein, we report the chemical synthesis, structure-activity relationship studies, downstream counterscreens, secondary assay data, and pharmacological profiling of the 2-aminobenzimidazole lead (compound 1c, ML130) as a potent and selective inhibitor of NOD 1-induced NF-kappa B activation.