Cyclopropyl-(2-methyl-2,3-dihydroindol-1-yl)methanone | 485769-26-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Cyclopropyl-(2-methyl-2,3-dihydroindol-1-yl)methanone
• CAS: 485769-26-4
• 化学式: C₁₃H₁₅NO
• mdl: MFCD02744863
• 分子量: 201.268
• InChiKey: NJIPGDYKLBDXJX-UHFFFAOYSA-N

物化性质

• 沸点：
  393.512±21.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.183±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Cyclopropyl-(2-methyl-2,3-dihydroindol-1-yl)methanone 在 氯磺酸 、 五氯化磷 作用下， 生成 1-(Cyclopropylcarbonyl)-2-methylindoline-5-sulfonyl chloride
  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
• 作为产物：
  描述：

  环丙基甲酰氯 、 2-甲基吲哚啉 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Cyclopropyl-(2-methyl-2,3-dihydroindol-1-yl)methanone
  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.