4-[2-(pyrrolo[2,3-b]pyridin-1-yl)ethoxy]benzaldehyde | 205371-31-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 4-[2-(pyrrolo[2,3-b]pyridin-1-yl)ethoxy]benzaldehyde
• 英文别名: 4-(2-pyrrolo[2,3-b]pyridin-1-ylethoxy)benzaldehyde
• CAS: 205371-31-9
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: WWEFFIYYHOTTBZ-UHFFFAOYSA-N

物化性质

• 沸点：
  490.5±30.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[2-(pyrrolo[2,3-b]pyridin-1-yl)ethoxy]benzaldehyde 在 palladium on activated charcoal sodium hydroxide 、 potassium tert-butylate 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、303.98 kPa 条件下， 反应 10.0h， 生成 2-ethoxy-3-[4-(2-pyrrolo[2,3-b]pyridin-1-ylethoxy)phenyl]propionic acid
  参考文献：
  名称：

  Synthesis and evaluation of azaindole-α-alkyloxyphenylpropionic acid analogues as PPARα/γ agonists

  摘要：

  A series of azaindole-alpha-alkyloxyphenylpropionic acid analogues was synthesized and evaluated for PPAR agonist activities. Structure-activity relationship was developed for PPAR alpha/gamma dual agonism. One of the synthesized compound 7a was identified as a potent, selective PPAR alpha/gamma dual agonist. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.040
• 作为产物：
  描述：

  7-氮杂吲哚 、 4-(2-溴乙氧基)苯甲醛 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-[2-(pyrrolo[2,3-b]pyridin-1-yl)ethoxy]benzaldehyde
  参考文献：
  名称：

  基于巴比妥酸的新型PPARgamma配体：虚拟筛选，合成和受体结合研究。

  摘要：

  利用虚拟筛选和分子对接方法，设计了一系列基于巴比妥酸（BA）的PPARγ配体。为了验证计算方法，合成了设计的分子并在体外放射性配体结合研究中进行了评估。在全部14个分子中，发现有6个与鼠PPARgamma结合，与参考标准吡格列酮相比，IC（50）的范围为0.1至2.5 microM（IC（50）= 0.7 microM）。

  DOI：

  10.1016/j.bmcl.2008.08.028

文献信息

• Novel heterocyclic derivatives, preparation method and pharmaceutical compositions containing same
  申请人：——

  公开号：US20030040533A1

  公开（公告）日：2003-02-27

  Compounds of formula (I): 1 wherein: X represents an oxygen atom or a sulphur atom or a group CH 2 or 2 R 1 and R 2 represent a hydrogen atom, or a group as defined in the description, A represents an alkylene chain as described in the description, B is as defined in the description, R 3 and R 4 represent a hydrogen atom or a group as defined in the description, D represents an optionally substituted benzene, optionally substituted pyrazine, optionally substituted pyrimidine or optionally substituted pyridazine nucleus.

  式(I)的化合物：1其中：X代表氧原子、硫原子或CH2或2R1和R2代表氢原子，或如说明书中所定义的基团，A代表如说明书中所描述的亚烷基链，B如说明书中所定义，R3和R4代表氢原子或如说明书中所定义的基团，D代表可任选取代的苯环、可任选取代的吡嗪环、可任选取代的嘧啶环或可任选取代的吡啶嗪环。
• Design and synthesis of 6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid derivatives as PPARγ activators
  作者：Rakesh Kumar、Amit Mittal、Uma Ramachandran

  DOI：10.1016/j.bmcl.2007.05.081

  日期：2007.8

  The design and synthesis of novel series of 6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid (pyrimidone) derivatives that are high affinity ligands for peroxisome proliferators activated receptor gamma have been reported as a potential substitute of 2.4-thiazolidinedione head group. The FlexX docking and radioligand binding affinity of some promising compounds of this series is comparable to that of thiazolidinedione based antidiabetic drugs currently in clinical use. (c) 2007 Elsevier Ltd. All rights reserved.
• Novel Euglycemic and Hypolipidemic Agents. 1
  作者：Braj B. Lohray、Vidya Bhushan、Bheema P. Rao、Gurram R. Madhavan、Nagabelli Murali、Krovvidi N. Rao、Ananth K. Reddy、Bagepalli M. Rajesh、Pamulapati G. Reddy、Ranjan Chakrabarti、Reeba K. Vikramadithyan、Ramanujam Rajagopalan、Rao N. V. S. Mamidi、Hemant K. Jajoo、Swaminathan Subramaniam

  DOI：10.1021/jm970444e

  日期：1998.5.1

  A series of [[(heterocyclyl)ethoxy]benzyl]-2,4-thiazolidinediones have been synthesized by the condensation of corresponding aldehyde 1 and 2,4-thiazolidinedione followed by hydrogenation. Both unsaturated thiazolidinedione 2 and its saturated counterpart 3 have shown antihyperglycemic activity. Many of these compounds have shown superior euglycemic and hypolipidemic activity compared to troglitazone (CS 045). The indole analogue DRF-2189 (3g) was found to be a very potent insulin sensitizer, comparable to BRL-49653 in genetically obese C57BL/6J-ob/ob and 57BL/KsJ-db/db mice. Pharmacokinetic and tissue distribution studies conducted on BRL-49653 and DRF-2189 (3g) indicate that these drugs are well-distributed in target tissues. On the basis of euglycemic activity as well as enhanced selectivity against reduction of triglycerides in plasma, DRF-2189 (3g) has been selected for further evaluation.
• DERIVES D'AZOLES CONDENSES ET LEUR UTILISATION COMME AGENTS HYPOGLYCEMIANTS
  申请人：Les Laboratoires Servier

  公开号：EP1252150B1

  公开（公告）日：2003-06-04
• US6919362B2
  申请人：——

  公开号：US6919362B2

  公开（公告）日：2005-07-19