[3-(1H-indol-3-yl)pyrrolidin-1-yl]-(2-methylphenyl)methanone | 1400941-63-0

• 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: [3-(1H-indol-3-yl)pyrrolidin-1-yl]-(2-methylphenyl)methanone
• CAS: 1400941-63-0
• 化学式: C₂₀H₂₀N₂O
• 分子量: 304.392
• InChiKey: IAMRTQDRZXQFNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (3-Indolyl)bernsteinsaeuredinitril 在 硫酸 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 37.5h， 生成 [3-(1H-indol-3-yl)pyrrolidin-1-yl]-(2-methylphenyl)methanone
  参考文献：
  名称：

  Structure-based design of 7-azaindole-pyrrolidine amides as inhibitors of 11β-hydroxysteroid dehydrogenase type I

  摘要：

  Indole-pyrrolidines were identified as inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) by high-throughput screening. Optimisation of the initial hit through structure-based design led to 7-azaindole-derivatives, with the best analogues displaying single digit nanomolar IC(50) potency. The modeling hypotheses were confirmed by solving the X-ray co-crystal structure of one of the lead compounds. These compounds were selective against 11β-hydroxysteroid dehydrogenase type 2 (selectivity ratio >200) and exhibited good inhibition of 11β-HSD1 (IC(50)<1μM) in a cellular model (3T3L1 adipocytes).

  DOI：

  10.1016/j.bmcl.2012.07.070

文献信息

• Structure-based design of 7-azaindole-pyrrolidine amides as inhibitors of 11β-hydroxysteroid dehydrogenase type I
  作者：Eric Valeur、Serge Christmann-Franck、Franck Lepifre、Denis Carniato、Daniel Cravo、Christine Charon、Sophie Bozec、Djordje Musil、Per Hillertz、Liliane Doare、Fabien Schmidlin、Marc Lecomte、Melanie Schultz、Didier Roche

  DOI：10.1016/j.bmcl.2012.07.070

  日期：2012.9

  Indole-pyrrolidines were identified as inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) by high-throughput screening. Optimisation of the initial hit through structure-based design led to 7-azaindole-derivatives, with the best analogues displaying single digit nanomolar IC(50) potency. The modeling hypotheses were confirmed by solving the X-ray co-crystal structure of one of the lead compounds. These compounds were selective against 11β-hydroxysteroid dehydrogenase type 2 (selectivity ratio >200) and exhibited good inhibition of 11β-HSD1 (IC(50)<1μM) in a cellular model (3T3L1 adipocytes).