2-(6-isopropoxy-3,4-dihydronaphth-2-yl)-1H-indole | 1057643-66-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(6-isopropoxy-3,4-dihydronaphth-2-yl)-1H-indole
• CAS: 1057643-66-9
• 化学式: C₂₁H₂₁NO
• 分子量: 303.404
• InChiKey: KMLZMNFZJJWKKO-UHFFFAOYSA-N

物化性质

• 沸点：
  493.0±45.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  25.02
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  顺式-(β-氰基)丙烯酸乙酯 、 2-(6-isopropoxy-3,4-dihydronaphth-2-yl)-1H-indole 在 ytterbium tribromide 作用下， 以 甲苯 为溶剂， 以50%的产率得到
  参考文献：
  名称：

  Mixed-Lineage Kinase 1 and Mixed-Lineage Kinase 3 Subtype-Selective Dihydronaphthyl[3,4-a]pyrrolo[3,4-c]carbazole-5-ones: Optimization, Mixed-Lineage Kinase 1 Crystallography, and Oral in Vivo Activity in 1-Methyl-4-phenyltetrahydropyridine Models

  摘要：

  The optimization of the dihydronaphthyl[3,4-a]pyrrolo[3,4-c]carbazole-5-one R(2) and R(12) positions led to the identification of the first MLK1 and MLK3 subtype-selective inhibitors within the MLK family. Compounds 14 (CEP-5104) and 16 (CEP-6331) displayed good potency for MLK1 and MLK3 inhibition with a greater than 30- to 100-fold selectivity for related family members MLK2 and DLK. Compounds 14 and 16 were orally active in vivo in a mouse MPTP biochemical efficacy model that was comparable to the first-generation pan-MLK inhibitor 1 (CEP-1347). The MLK1 structure-activity relationships were supported by the first-reported X-ray crystal structure of MLK1 bound with 16.

  DOI：

  10.1021/jm8005838
• 作为产物：
  描述：

  吲哚 、 3-bromo-7-isopropoxy-1,2-dihydronaphthalene 在 正丁基锂 、 二氧化碳 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.25h， 以81%的产率得到2-(6-isopropoxy-3,4-dihydronaphth-2-yl)-1H-indole
  参考文献：
  名称：

  Mixed-Lineage Kinase 1 and Mixed-Lineage Kinase 3 Subtype-Selective Dihydronaphthyl[3,4-a]pyrrolo[3,4-c]carbazole-5-ones: Optimization, Mixed-Lineage Kinase 1 Crystallography, and Oral in Vivo Activity in 1-Methyl-4-phenyltetrahydropyridine Models

  摘要：

  The optimization of the dihydronaphthyl[3,4-a]pyrrolo[3,4-c]carbazole-5-one R(2) and R(12) positions led to the identification of the first MLK1 and MLK3 subtype-selective inhibitors within the MLK family. Compounds 14 (CEP-5104) and 16 (CEP-6331) displayed good potency for MLK1 and MLK3 inhibition with a greater than 30- to 100-fold selectivity for related family members MLK2 and DLK. Compounds 14 and 16 were orally active in vivo in a mouse MPTP biochemical efficacy model that was comparable to the first-generation pan-MLK inhibitor 1 (CEP-1347). The MLK1 structure-activity relationships were supported by the first-reported X-ray crystal structure of MLK1 bound with 16.

  DOI：

  10.1021/jm8005838