ethyl ((1S)-5-{3-[(2-chloro-5-methyl-4-pyrimidinyl)(methyl)amino]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate | 724469-17-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: ethyl ((1S)-5-{3-[(2-chloro-5-methyl-4-pyrimidinyl)(methyl)amino]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate
• 英文别名: ethyl 2-[(1S)-5-[3-[(2-chloro-5-methylpyrimidin-4-yl)-methylamino]propoxy]-2,3-dihydro-1H-inden-1-yl]acetate
• CAS: 724469-17-4
• 化学式: C₂₂H₂₈ClN₃O₃
• 分子量: 417.936
• InChiKey: DAWJLVUUHOPNNK-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl ((1S)-5-{3-[(2-chloro-5-methyl-4-pyrimidinyl)(methyl)amino]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate 在 lithium hydroxide 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 sodium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 水 、 甲苯 为溶剂， 生成 2-[(1S)-5-(3-{[2-(4-ethoxyphenyl)-5-methylpyrimidin-4-yl](methyl)amino}propoxy)indan-1-yl]acetic acid
  参考文献：
  名称：

  Indanylacetic acid derivatives carrying aryl-pyridyl and aryl-pyrimidinyl tail groups—new classes of PPAR γ/δ and PPAR α/γ/δ agonists

  摘要：

  Modulation of PPAR activities represents an attractive approach for the treatment of diabetes with associated cardiovascular complications. The indanylacetic acid structural motif has proven useful in the generation of potent and tunable PPAR ligands. Modification of the substituents on the linker and the heterocycle tail group allowed for the modulation of the selectivity at the different receptor subtypes. Compound 33 was evaluated in vivo, where it displayed the desired reduction of glucose levels and increase in HDL levels in various animal models. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.025
• 作为产物：
  描述：

  5-甲氧基-1-茚酮 在 palladium on activated charcoal sodium hydroxide 、 三甲基氯硅烷 、 三氯化铝 、 氢气 、 sodium hydride 、 三苯基膦 、 乙硫醇 、 锌 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 5.0~40.0 ℃ 、275.79 kPa 条件下， 生成 ethyl ((1S)-5-{3-[(2-chloro-5-methyl-4-pyrimidinyl)(methyl)amino]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate
  参考文献：
  名称：

  Indanylacetic acid derivatives carrying aryl-pyridyl and aryl-pyrimidinyl tail groups—new classes of PPAR γ/δ and PPAR α/γ/δ agonists

  摘要：

  Modulation of PPAR activities represents an attractive approach for the treatment of diabetes with associated cardiovascular complications. The indanylacetic acid structural motif has proven useful in the generation of potent and tunable PPAR ligands. Modification of the substituents on the linker and the heterocycle tail group allowed for the modulation of the selectivity at the different receptor subtypes. Compound 33 was evaluated in vivo, where it displayed the desired reduction of glucose levels and increase in HDL levels in various animal models. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.025

文献信息

• Indane acetic acid derivatives and their use as pharmaceutical agents, intermediates, and method of preparation
  申请人：Cantin Louis-David

  公开号：US20060084680A1

  公开（公告）日：2006-04-20

  This invention relates to novel indane acetic acid derivatives which are useful in the treatment of diseases such as diabetes, obesity, hyperlipidemia, and atherosclerotic diseases. The invention also relates to intermediates useful in preparation of indane acetic derivatives and to methods of preparation.

  本发明涉及一种新型的茚三酸衍生物，其可用于治疗糖尿病、肥胖症、高脂血症和动脉粥样硬化等疾病。本发明还涉及用于制备茚三酸衍生物的中间体以及制备方法。
• INDANE ACETIC ACID DERIVATIVES AND THEIR USE AS PHARMACEUTICAL AGENTS, INTERMEDIATES, AND METHOD OF PREPARATION
  申请人：Bayer Pharmaceuticals Corporation

  公开号：EP1578715B1

  公开（公告）日：2011-03-02
• US7714004B2
  申请人：——

  公开号：US7714004B2

  公开（公告）日：2010-05-11
• US7906653B2
  申请人：——

  公开号：US7906653B2

  公开（公告）日：2011-03-15
• Indanylacetic acid derivatives carrying aryl-pyridyl and aryl-pyrimidinyl tail groups—new classes of PPAR γ/δ and PPAR α/γ/δ agonists
  作者：Louis-David Cantin、Sidney Liang、Herbert Ogutu、Christiana I. Iwuagwu、Ken Boakye、William H. Bullock、Michael Burns、Roger Clark、Thomas Claus、Fernando E. delaCruz、Michelle Daly、Frederick J. Ehrgott、Jeffrey S. Johnson、Christine Keiper、James N. Livingston、Robert W. Schoenleber、Jeffrey Shapiro、Christopher Town、Ling Yang、Manami Tsutsumi、Xin Ma

  DOI：10.1016/j.bmcl.2006.11.025

  日期：2007.2

  Modulation of PPAR activities represents an attractive approach for the treatment of diabetes with associated cardiovascular complications. The indanylacetic acid structural motif has proven useful in the generation of potent and tunable PPAR ligands. Modification of the substituents on the linker and the heterocycle tail group allowed for the modulation of the selectivity at the different receptor subtypes. Compound 33 was evaluated in vivo, where it displayed the desired reduction of glucose levels and increase in HDL levels in various animal models. (c) 2006 Elsevier Ltd. All rights reserved.