rac-2-Ethoxy-3-(3-methyl-1H-indol-5-yl)-propionic acid ethyl ester | 671215-50-2

• 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: rac-2-Ethoxy-3-(3-methyl-1H-indol-5-yl)-propionic acid ethyl ester
• 英文别名: ethyl 2-ethoxy-3-(3-methyl-1H-indol-5-yl)propanoate
• CAS: 671215-50-2
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: ROZSXAMUJLRIMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloromethyl-5-methyl-2-(4-(2-propyl)-phenyl)-oxazole 、 rac-2-Ethoxy-3-(3-methyl-1H-indol-5-yl)-propionic acid ethyl ester 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以67%的产率得到rac-2-Ethoxy-3-{1-[2-(4-isopropyl-phenyl)-5-methyl-oxazol-4-ylmethyl]-3-methyl-1H-indol-5-yl}-propionic Acid Ethyl Ester
  参考文献：
  名称：

  Indolyl derivatives

  摘要：

  提供了式I的化合物，以及其药用可接受的盐和酯，其中R1至R8，A，A1和n具有规范中指示的含义。

  公开号：

  US20040053979A1
• 作为产物：
  描述：

  (1,2-二乙氧基-2-氧代乙基)(三苯基)鏻氯化物 在 palladium on activated charcoal 1,1,2,3-四甲基胍 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 22.0~40.0 ℃ 、101.33 kPa 条件下， 生成 rac-2-Ethoxy-3-(3-methyl-1H-indol-5-yl)-propionic acid ethyl ester
  参考文献：
  名称：

  Structure-based design of indole propionic acids as novel PPARα/γ co-agonists

  摘要：

  In the quest for novel PPARalpha/gamma co-agonists as putative drugs for the treatment of type 2 diabetes and dyslipidemia, we have used a structure-based design approach to identify propionic acids with a 1,5-disubstituted indole scaffold as potent PPARalpha/gamma activators. Compounds 13, 24, and 28 are examples of submicromolar dual agonists with different alpha/gamma EC50 ratios that are selective against the delta-isoform. Analysis of the X-ray complex structure of PPARgamma with the indole propionic acid 13 provides a rationalization for some of the observed SAR.

  DOI：

  10.1016/j.bmcl.2006.05.007

文献信息

• N-SUBSTITUTED-1H-INDOL-5-PROPIONIC ACID COMPOUNDS AS PPAR AGONISTS USEFUL FOR THE TREATMENT OF DIABETES
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1539746A1

  公开（公告）日：2005-06-15
• US6890947B2
  申请人：——

  公开号：US6890947B2

  公开（公告）日：2005-05-10
• [EN] N-SUBSTITUTED-1H-INDOL-5-PROPIONIC ACID COMPOUNDS AS PPAR AGONISTS USEFUL FOR THE TREATMENT OF DIABETES<br/>[FR] COMPOSES D'ACIDE 1H-INDOL-5-PROPIONIQUE A SUBSTITUTION N EN TANT QU'AGONISTES DE PPAR UTILES DANS LE TRAITEMENT DU DIABETE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2004024726A1

  公开（公告）日：2004-03-25

  Compounds of formula (I), as well as pharmaceutically acceptable salts and esters thereof, wherein R1 to R8, A, A1 and n have the significance given in claim 1 can be used in the form of pharmaceutical preparations.
• Indolyl derivatives
  申请人：——

  公开号：US20040053979A1

  公开（公告）日：2004-03-18

  Compounds of formula I are provided 1 as well as pharmaceutically acceptable salts and esters thereof, wherein R 1 to R 8 , A, A 1 and n have the significance indicated in the specification.

  提供了式I的化合物，以及其药用可接受的盐和酯，其中R1至R8，A，A1和n具有规范中指示的含义。
• Structure-based design of indole propionic acids as novel PPARα/γ co-agonists
  作者：Bernd Kuhn、Hans Hilpert、Jörg Benz、Alfred Binggeli、Uwe Grether、Roland Humm、Hans Peter Märki、Markus Meyer、Peter Mohr

  DOI：10.1016/j.bmcl.2006.05.007

  日期：2006.8

  In the quest for novel PPARalpha/gamma co-agonists as putative drugs for the treatment of type 2 diabetes and dyslipidemia, we have used a structure-based design approach to identify propionic acids with a 1,5-disubstituted indole scaffold as potent PPARalpha/gamma activators. Compounds 13, 24, and 28 are examples of submicromolar dual agonists with different alpha/gamma EC50 ratios that are selective against the delta-isoform. Analysis of the X-ray complex structure of PPARgamma with the indole propionic acid 13 provides a rationalization for some of the observed SAR.