1-benzyl-1H-pyrrolo[2,3-b]pyridine-6-carboxylic acid methyl ester

• 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: 1-benzyl-1H-pyrrolo[2,3-b]pyridine-6-carboxylic acid methyl ester
• 英文别名: 1-Benzyl-1H-pyrrolo[2,3-b]pyridine-6-carboxylic acid methyl ester；methyl 1-benzylpyrrolo[2,3-b]pyridine-6-carboxylate
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: UOUVWTAIXJPGTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  4
• 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

• 作为产物：
  描述：

  5-Azaspiro[2.5]oct-7-ene-4,6-dione 在 manganese(IV) oxide 、 bis-triphenylphosphine-palladium(II) chloride 、 4 A molecular sieve 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 110.0 ℃ 、101.33 kPa 条件下， 反应 31.0h， 生成 1-benzyl-1H-pyrrolo[2,3-b]pyridine-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and Cross-Coupling Reactions of 7-Azaindoles via a New Donor−Acceptor Cyclopropane

  摘要：

  A new type of donor-acceptor cyclopropane has been prepared from commercially available cyclopropane- 1,1-diesters. This cyclopropane reacts with triflic anhydride to produce an isolable tristrifloxy intermediate which when treated with primary amines gives 6-trifloxy-7-azaindolines which in turn can be dehydrogenated to the azaindoles. The 6-trifloxy substituent can be used to introduce diversity at this position via a variety of cross-coupling reactions thus preparing potentially interesting compounds based on the important 7-azaindole pharmacophore.

  DOI：

  10.1021/ol061379i

文献信息

• [EN] GPR40 RECEPTOR AGONIST, METHODS OF PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AS AN ACTIVE INGREDIENT<br/>[FR] AGONISTE DU RÉCEPTEUR GPR40, PROCÉDÉS DE PRÉPARATION DE CELUI-CI, ET COMPOSITIONS PHARMACEUTIQUES CONTENANT CELUI-CI EN TANT QUE SUBSTANCE ACTIVE
  申请人：LG LIFE SCIENCES LTD

  公开号：WO2014073904A1

  公开（公告）日：2014-05-15

  The present invention relates to a novel compound having GPR40 receptor agonist activity that promotes insulin secretion and inhibits blood sugar rise after glucose loading, and is thereby useful for the treatment of diabetes and complications thereof, the preparation method thereof and pharmaceutical composition containing them as an active ingredient.

  本发明涉及一种具有GPR40受体激动剂活性的新化合物，可促进胰岛素分泌并抑制葡萄糖负荷后血糖升高，因此适用于糖尿病及其并发症的治疗，以及包含它们作为活性成分的制备方法和药物组合物。
• GPR40 RECEPTOR AGONIST, METHODS OF PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AS AN ACTIVE AGENT
  申请人：LG LIFE SCIENCES LTD.

  公开号：US20150291584A1

  公开（公告）日：2015-10-15

  The present invention relates to a novel compound having GPR40 receptor agonist activity that promotes insulin secretion and inhibits blood sugar rise after glucose loading, and is thereby useful for the treatment of diabetes and complications thereof, the preparation method thereof and pharmaceutical composition containing them as an active ingredient.

  本发明涉及一种新型化合物，具有GPR40受体激动剂活性，促进胰岛素分泌并抑制葡萄糖负荷后血糖升高，因此可用于糖尿病及其并发症的治疗，其制备方法和含有其作为活性成分的药物组合物。
• GPR40 RECEPTOR AGONIST, METHODS OF PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AS AN ACTIVE INGREDIENT
  申请人：LG Life Sciences Ltd.

  公开号：EP2917180A1

  公开（公告）日：2015-09-16
• US9988379B2
  申请人：——

  公开号：US9988379B2

  公开（公告）日：2018-06-05
• Synthesis and Cross-Coupling Reactions of 7-Azaindoles via a New Donor−Acceptor Cyclopropane
  作者：Xiaomei Zheng、Michael A. Kerr

  DOI：10.1021/ol061379i

  日期：2006.8.1

  A new type of donor-acceptor cyclopropane has been prepared from commercially available cyclopropane- 1,1-diesters. This cyclopropane reacts with triflic anhydride to produce an isolable tristrifloxy intermediate which when treated with primary amines gives 6-trifloxy-7-azaindolines which in turn can be dehydrogenated to the azaindoles. The 6-trifloxy substituent can be used to introduce diversity at this position via a variety of cross-coupling reactions thus preparing potentially interesting compounds based on the important 7-azaindole pharmacophore.