{4-[6-(5-chloro-2,3-dihydrobenzofuran-7-yl)-4-hydroxy-6-methyl-4-trifluoromethylhept-1-ynyl]pyridin-3-yl}carbamic acid tert-butyl ester | 1245526-97-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: {4-[6-(5-chloro-2,3-dihydrobenzofuran-7-yl)-4-hydroxy-6-methyl-4-trifluoromethylhept-1-ynyl]pyridin-3-yl}carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[4-[6-(5-chloro-2,3-dihydro-1-benzofuran-7-yl)-4-hydroxy-6-methyl-4-(trifluoromethyl)hept-1-ynyl]pyridin-3-yl]carbamate
• CAS: 1245526-97-9
• 化学式: C₂₇H₃₀ClF₃N₂O₄
• 分子量: 538.994
• InChiKey: VNHBKZXRIVURHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  80.7
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  {4-[6-(5-chloro-2,3-dihydrobenzofuran-7-yl)-4-hydroxy-6-methyl-4-trifluoromethylhept-1-ynyl]pyridin-3-yl}carbamic acid tert-butyl ester 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 以100%的产率得到1-(3-aminopyridin-4-yl)-6-(5-chloro-2,3-dihydrobenzofuran-7-yl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol hydrochloride
  参考文献：
  名称：

  Nonsteroidal Dissociated Glucocorticoid Agonists Containing Azaindoles as Steroid A-Ring Mimetics

  摘要：

  Syntheses and structure activity relationships (SA R) of nonsteroidal glucocorticoid receptor (GR) agonists are described. These compounds contain azaindole moieties as A-ring mimetics and display various degrees of in vitro dissociation between gene transrepression and transactivation. Collagen induced arthritis studies in mouse have demonstrated that in vitro dissociated compounds (R)-16 and (R)-37 have steroid-like anti-inflammatory properties with improved metabolic side effect profiles, such as a reduced increase in body fat and scrum insulin levels, compared to steroids.

  DOI：

  10.1021/jm100751q
• 作为产物：
  描述：

  6-(5-chloro-2,3-dihydrobenzofuran-7-yl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol 、 叔-丁基-7-氨基-3,4-二氢异喹啉-2(1H)-甲酸 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以73%的产率得到{4-[6-(5-chloro-2,3-dihydrobenzofuran-7-yl)-4-hydroxy-6-methyl-4-trifluoromethylhept-1-ynyl]pyridin-3-yl}carbamic acid tert-butyl ester
  参考文献：
  名称：

  Nonsteroidal Dissociated Glucocorticoid Agonists Containing Azaindoles as Steroid A-Ring Mimetics

  摘要：

  Syntheses and structure activity relationships (SA R) of nonsteroidal glucocorticoid receptor (GR) agonists are described. These compounds contain azaindole moieties as A-ring mimetics and display various degrees of in vitro dissociation between gene transrepression and transactivation. Collagen induced arthritis studies in mouse have demonstrated that in vitro dissociated compounds (R)-16 and (R)-37 have steroid-like anti-inflammatory properties with improved metabolic side effect profiles, such as a reduced increase in body fat and scrum insulin levels, compared to steroids.

  DOI：

  10.1021/jm100751q

文献信息

• Nonsteroidal Dissociated Glucocorticoid Agonists Containing Azaindoles as Steroid A-Ring Mimetics
  作者：Doris Riether、Christian Harcken、Hossein Razavi、Daniel Kuzmich、Thomas Gilmore、Jörg Bentzien、Edward J. Pack、Donald Souza、Richard M. Nelson、Alison Kukulka、Tazmeen N. Fadra、Ljiljana Zuvela-Jelaska、Josephine Pelletier、Roger Dinallo、Mark Panzenbeck、Carol Torcellini、Gerald H. Nabozny、David S. Thomson

  DOI：10.1021/jm100751q

  日期：2010.9.23

  Syntheses and structure activity relationships (SA R) of nonsteroidal glucocorticoid receptor (GR) agonists are described. These compounds contain azaindole moieties as A-ring mimetics and display various degrees of in vitro dissociation between gene transrepression and transactivation. Collagen induced arthritis studies in mouse have demonstrated that in vitro dissociated compounds (R)-16 and (R)-37 have steroid-like anti-inflammatory properties with improved metabolic side effect profiles, such as a reduced increase in body fat and scrum insulin levels, compared to steroids.