tert-butyl 2-(7-(4-(fluoromethoxy)-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate | 1215119-02-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl 2-(7-(4-(fluoromethoxy)-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate
• 英文别名: tert-butyl 2-[6-[[4-(fluoromethoxy)-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1H-pyrrolo[1,2-a]indol-3-yl]acetate
• CAS: 1215119-02-0
• 化学式: C₂₆H₂₇F₄NO₄
• 分子量: 493.498
• InChiKey: UTAFTASXPOHLLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(7-(4-(fluoromethoxy)-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate 在 DL-半胱氨酸 、 三氟乙酸 作用下， 反应 0.25h， 生成 2-(7-(4-(fluoromethoxy)-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid
  参考文献：
  名称：

  (7-Benzyloxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acids as S1P₁ Functional Antagonists

  摘要：

  S1P(1) is a validated target for treatment of autoimmune disease, and functional antagonists with superior safety and pharmacokinetic properties are being sought as second generation therapeutics. We describe the discovery and optimization of (7-benzyloxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acids as potent, centrally available, direct acting S1P(1) functional antagonists, with favorable pharmacokinetic and safety properties.

  DOI：

  10.1021/ml500422m
• 作为产物：
  描述：

  (叔丁氧基羰基亚甲基)三苯基磷烷 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 palladium 10% on activated carbon 、 氢气 、 双氧水 、 potassium acetate 、 potassium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 23.0~90.0 ℃ 、655.02 kPa 条件下， 反应 36.92h， 生成 tert-butyl 2-(7-(4-(fluoromethoxy)-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate
  参考文献：
  名称：

  (7-Benzyloxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acids as S1P₁ Functional Antagonists

  摘要：

  S1P(1) is a validated target for treatment of autoimmune disease, and functional antagonists with superior safety and pharmacokinetic properties are being sought as second generation therapeutics. We describe the discovery and optimization of (7-benzyloxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acids as potent, centrally available, direct acting S1P(1) functional antagonists, with favorable pharmacokinetic and safety properties.

  DOI：

  10.1021/ml500422m

文献信息

• (7-Benzyloxy-2,3-dihydro-<i>1H</i>-pyrrolo[1,2-<i>a</i>]indol-1-yl)acetic Acids as S1P₁ Functional Antagonists
  作者：Daniel J. Buzard、Luis Lopez、Jeanne Moody、Andrew Kawasaki、Thomas O. Schrader、Michelle Kasem、Ben Johnson、Xiuwen Zhu、Lars Thoresen、Sun Hee Kim、Tawfik Gharbaoui、Dipanjan Sengupta、Lorene Calvano、Ashwin Krishnan、Yinghong Gao、Graeme Semple、Jeff Edwards、Jeremy Barden、Michael Morgan、Khawja Usmani、Chuan Chen、Abu Sadeque、Weichao Chen、Ronald J. Christopher、Jayant Thatte、Lixia Fu、Michelle Solomon、Kevin Whelan、Hussien Al-Shamma、Joel Gatlin、Ibragim Gaidarov、Todd Anthony、Minh Le、David J. Unett、Scott Stirn、Anthony Blackburn、Dominic P. Behan、Robert M. Jones

  DOI：10.1021/ml500422m

  日期：2014.12.11

  S1P(1) is a validated target for treatment of autoimmune disease, and functional antagonists with superior safety and pharmacokinetic properties are being sought as second generation therapeutics. We describe the discovery and optimization of (7-benzyloxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acids as potent, centrally available, direct acting S1P(1) functional antagonists, with favorable pharmacokinetic and safety properties.