1-[[3-(Trifluoromethyl)phenyl]methyl]indole-2-carboxylic acid | 915701-01-8

• 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: 1-[[3-(Trifluoromethyl)phenyl]methyl]indole-2-carboxylic acid
• CAS: 915701-01-8
• 化学式: C₁₇H₁₂F₃NO₂
• 分子量: 319.283
• InChiKey: YUPKNTFJGUKTJO-UHFFFAOYSA-N

物化性质

• 沸点：
  480.7±45.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[[3-(Trifluoromethyl)phenyl]methyl]indole-2-carboxylic acid 、 2-氯噻吩-5-磺酰胺 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-(3-(trifluoromethyl)benzyl)-N-(5-chlorothiophen-2-ylsulfonyl)-1H-indole-2-carboxamide
  参考文献：
  名称：

  Design and synthesis of novel N-sulfonyl-2-indole carboxamides as potent PPAR-γ binding agents with potential application to the treatment of osteoporosis

  摘要：

  The synthesis and structure-activity relationships of a novel series of N-sulfonyl-2-indole carboxamides that bind to peroxisome proliferator-activated receptor gamma (PPAR-gamma) are reported. Chemical optimization of the series led to the identification of 4q (IC(50)=50 nM) as a potent binding agent of PPAR-gamma. Also reported is preliminary cell based data suggesting the use of these compounds in the treatment of osteoporosis.

  DOI：

  10.1016/j.bmcl.2006.08.003
• 作为产物：
  描述：

  吲哚-2-羧酸乙酯 在 氢氧化钾 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-[[3-(Trifluoromethyl)phenyl]methyl]indole-2-carboxylic acid
  参考文献：
  名称：

  Design and synthesis of novel N-sulfonyl-2-indole carboxamides as potent PPAR-γ binding agents with potential application to the treatment of osteoporosis

  摘要：

  The synthesis and structure-activity relationships of a novel series of N-sulfonyl-2-indole carboxamides that bind to peroxisome proliferator-activated receptor gamma (PPAR-gamma) are reported. Chemical optimization of the series led to the identification of 4q (IC(50)=50 nM) as a potent binding agent of PPAR-gamma. Also reported is preliminary cell based data suggesting the use of these compounds in the treatment of osteoporosis.

  DOI：

  10.1016/j.bmcl.2006.08.003

文献信息

• INDOLE DERIVATIVES AND THEIR USE AS MCP-1 ANTAGONISTS
  申请人：AstraZeneca AB

  公开号：EP1003504B1

  公开（公告）日：2003-07-02
• INDOLE DERIVATIVES AND THEIR USE AS MCP-1 RECEPTOR ANTAGONISTS
  申请人：AstraZeneca AB

  公开号：EP1150952B1

  公开（公告）日：2004-10-27
• SUBSTITUTED INDOLES, PHARMACEUTICAL COMPOSITIONS CONTAINING SUCH INDOLES AND THEIR USE AS PPAR-$g(g) BINDING AGENTS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP1341761A1

  公开（公告）日：2003-09-10
• DERIVES DE N-(1 H-INDOLYL)-I H-IND0LE-2-CARB0XAMIDES, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE
  申请人：Sanofi-Aventis

  公开号：EP1776340A1

  公开（公告）日：2007-04-25
• [EN] SUBSTITUTED INDOLES, PHARMACEUTICAL COMPOSITIONS CONTAINING SUCH INDOLES AND THEIR USE AS PPAR- gamma BINDING AGENTS<br/>[FR] INDOLES SUBSTITUEES, COMPOSITIONS PHARMACEUTIQUES CONTENANT CES INDOLES ET LEUR UTILISATION COMME AGENT DE FIXATION DE PPAR- DOLLAR G(G)
  申请人：BAYER AG

  公开号：WO2002030895A1

  公开（公告）日：2002-04-18

  Disclosed are substituted indoles, pharmaceutical compositions containing such indoles, and their use in treating or preventing PPAR-η mediated diseases or conditions, such as osteopenia, osteoporosis, cancer, diabetes and atherosclerosis.