6-(2,3-dihydrobenzofuran-7-yl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol | 1245526-95-7

• 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: 6-(2,3-dihydrobenzofuran-7-yl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol
• 英文别名: 6-(2,3-Dihydro-1-benzofuran-7-yl)-6-methyl-4-(trifluoromethyl)hept-1-yn-4-ol
• CAS: 1245526-95-7
• 化学式: C₁₇H₁₉F₃O₂
• 分子量: 312.332
• InChiKey: YHIUKQCJNSYJNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(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64%的产率得到{4-[6-(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
• 作为产物：
  描述：

  4-(2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-one 、 3-溴丙炔 在 氢化铝 、 mercury dichloride 作用下， 以 四氢呋喃 、 甲苯 、 乙醚 为溶剂， 反应 1.0h， 以95%的产率得到6-(2,3-dihydrobenzofuran-7-yl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol
  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.