Ethyl 6-benzyl-4-(2,4-dichlorophenyl)-2-methyl-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine-3-carboxylate | 915296-87-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Ethyl 6-benzyl-4-(2,4-dichlorophenyl)-2-methyl-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine-3-carboxylate
• 英文别名: ethyl 6-benzyl-4-(2,4-dichlorophenyl)-2-methyl-7-oxo-5H-pyrrolo[3,4-b]pyridine-3-carboxylate
• CAS: 915296-87-6
• 化学式: C₂₄H₂₀Cl₂N₂O₃
• 分子量: 455.34
• InChiKey: FHYDKFZEFXUEJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  59.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 6-benzyl-4-(2,4-dichlorophenyl)-2-methyl-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine-3-carboxylate 在 lithium aluminium tetrahydride 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.33h， 生成 6-benzyl-3-(chloromethyl)-4-(2,4-dichlorophenyl)-2-methyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine
  参考文献：
  名称：

  7-Oxopyrrolopyridine-derived DPP4 inhibitors—mitigation of CYP and hERG liabilities via introduction of polar functionalities in the active site

  摘要：

  Design, synthesis, and SAR of 7-oxopyrrolopyridine-derived DPP4 inhibitors are described. The preferred stereochemistry of these atropisomeric biaryl analogs has been identified as Sa. Compound (+)-3t, with a K-i against DPP4, DPP8, and DPP9 of 0.37 nM, 2.2, and 5.7 mu M, respectively, showed a significant improvement in insulin response after single doses of 3 and 10 mu mol/kg in ob/ob mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.074
• 作为产物：
  描述：

  3-(苄基氨基)丙酸乙酯 在 硝酸 、 sodium ethanolate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 Ethyl 6-benzyl-4-(2,4-dichlorophenyl)-2-methyl-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine-3-carboxylate
  参考文献：
  名称：

  7-Oxopyrrolopyridine-derived DPP4 inhibitors—mitigation of CYP and hERG liabilities via introduction of polar functionalities in the active site

  摘要：

  Design, synthesis, and SAR of 7-oxopyrrolopyridine-derived DPP4 inhibitors are described. The preferred stereochemistry of these atropisomeric biaryl analogs has been identified as Sa. Compound (+)-3t, with a K-i against DPP4, DPP8, and DPP9 of 0.37 nM, 2.2, and 5.7 mu M, respectively, showed a significant improvement in insulin response after single doses of 3 and 10 mu mol/kg in ob/ob mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.074

文献信息

• Pyrrolopyridine-based inhibitors of dipeptidyl peptidase IV and methods
  申请人：Devasthale Pratik

  公开号：US20060264457A1

  公开（公告）日：2006-11-23

  Compounds are provided having the formula (I) wherein R, X, Y, Z, A and n are as defined herein, which are inhibitors of dipeptidyl peptidase IV and thus are useful in treating diabetes and related diseases.

  提供的化合物具有以下式(I)的结构，其中R、X、Y、Z、A和n的定义如本文所述，这些化合物是二肽基肽酶IV的抑制剂，因此在治疗糖尿病和相关疾病方面是有用的。
• PYRROLOPYRIDINE-BASED INHIBITORS OF DIPEPTIDYL PEPTIDASE IV AND METHODS
  申请人：Bristol-Myers Squibb Company

  公开号：EP1888589B1

  公开（公告）日：2012-05-09
• US7521557B2
  申请人：——

  公开号：US7521557B2

  公开（公告）日：2009-04-21