4-(5-甲氧基-1H-吲哚-3-基)-1-哌啶甲酸叔丁酯 | 951174-11-1

• 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
• 中文名称: 4-(5-甲氧基-1H-吲哚-3-基)-1-哌啶甲酸叔丁酯
• 英文名称: tert-butyl 4-(5-methoxy-1H-indol-3-yl)piperidine-1-carboxylate
• CAS: 951174-11-1
• 化学式: C₁₉H₂₆N₂O₃
• 分子量: 330.427
• InChiKey: VTNYLHQQIXRGSF-UHFFFAOYSA-N

物化性质

• 沸点：
  492.0±45.0 °C(Predicted)
• 密度：
  1.158

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-(5-甲氧基-1H-吲哚-3-基)-1-哌啶甲酸叔丁酯 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到5-甲氧基-3-哌啶-4-基-1H-吲哚
  参考文献：
  名称：

  Pyrazole-based cathepsin S inhibitors with improved cellular potency

  摘要：

  High potency pyrazole-based noncovalent inhibitors of human cathepsin S (CatS) were developed by modification of the benzo-fused 5-membered ring heterocycles found in earlier series of Cats inhibitors. Although substitutions on this heterocyclic framework had a moderate impact on enzymatic potency, dramatic effects on cellular activity were observed. Optimization afforded indole- and benzothiophene-derived analogues that were high affinity Cats inhibitors (IC50 = 20-40 nM) with good cellular potency (IC50 = 30-340 nM). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.08.038
• 作为产物：
  描述：

  4-(5-methoxy-1H-indol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以75%的产率得到4-(5-甲氧基-1H-吲哚-3-基)-1-哌啶甲酸叔丁酯
  参考文献：
  名称：

  N1-Azinylsulfonyl-1H-indoles: 5-HT6 Receptor Antagonists with Procognitive and Antidepressant-Like Properties

  摘要：

  A series of N1-azinylsulfonyl-3-(1,2,3,6,tetrahyrdopyridin-4-yl)-1H-indole derivatives was designed to obtain highly potent 5-HT6 receptor ligands. The study allowed for the identification of 25 (4-{[5-methoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-1-yl]sulfonyl}isoquinoline), a potent and selective 5-HT6 receptor antagonist. The selected compound, was evaluated in vivo in a novel object recognition (NOR) and forced swim (FST) tests in rats, demonstrating distinct pro-cognitive and antidepressant-like properties (MED = 1 mg/kg and 0.1 mg/kg, i.p., respectively). Compound SB-742457, used as comparator, reversed memory deficits in NOR task in similar doses, while in FST it was active in 10-30-fold higher dose (3 mg/kg). In contrast to SB-742457, which was active in Vogel test (MED = 3 mg/kg), compound 25 displayed no anxiolytic activity.

  DOI：

  10.1021/acsmedchemlett.6b00056

文献信息

• Pyrazole-based cathepsin S inhibitors with improved cellular potency
  作者：Jianmei Wei、Barbara A. Pio、Hui Cai、Steven P. Meduna、Siquan Sun、Yin Gu、Wen Jiang、Robin L. Thurmond、Lars Karlsson、James P. Edwards

  DOI：10.1016/j.bmcl.2007.08.038

  日期：2007.10

  High potency pyrazole-based noncovalent inhibitors of human cathepsin S (CatS) were developed by modification of the benzo-fused 5-membered ring heterocycles found in earlier series of Cats inhibitors. Although substitutions on this heterocyclic framework had a moderate impact on enzymatic potency, dramatic effects on cellular activity were observed. Optimization afforded indole- and benzothiophene-derived analogues that were high affinity Cats inhibitors (IC50 = 20-40 nM) with good cellular potency (IC50 = 30-340 nM). (c) 2007 Elsevier Ltd. All rights reserved.
• <i>N</i>1-Azinylsulfonyl-1<i>H</i>-indoles: 5-HT6 Receptor Antagonists with Procognitive and Antidepressant-Like Properties
  作者：Paweł Zajdel、Krzysztof Marciniec、Grzegorz Satała、Vittorio Canale、Tomasz Kos、Anna Partyka、Magdalena Jastrzębska-Więsek、Anna Wesołowska、Agnieszka Basińska-Ziobroń、Jacek Wójcikowski、Władysława A. Daniel、Andrzej J. Bojarski、Piotr Popik

  DOI：10.1021/acsmedchemlett.6b00056

  日期：2016.6.9

  A series of N1-azinylsulfonyl-3-(1,2,3,6,tetrahyrdopyridin-4-yl)-1H-indole derivatives was designed to obtain highly potent 5-HT6 receptor ligands. The study allowed for the identification of 25 (4-[5-methoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-1-yl]sulfonyl}isoquinoline), a potent and selective 5-HT6 receptor antagonist. The selected compound, was evaluated in vivo in a novel object recognition (NOR) and forced swim (FST) tests in rats, demonstrating distinct pro-cognitive and antidepressant-like properties (MED = 1 mg/kg and 0.1 mg/kg, i.p., respectively). Compound SB-742457, used as comparator, reversed memory deficits in NOR task in similar doses, while in FST it was active in 10-30-fold higher dose (3 mg/kg). In contrast to SB-742457, which was active in Vogel test (MED = 3 mg/kg), compound 25 displayed no anxiolytic activity.