Methyl 4-(2,4-dichlorophenyl)-2-methyl-7-oxo-5,6-dihydropyrrolo[3,4-b]pyridine-3-carboxylate | 915297-24-4

• 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: Methyl 4-(2,4-dichlorophenyl)-2-methyl-7-oxo-5,6-dihydropyrrolo[3,4-b]pyridine-3-carboxylate
• CAS: 915297-24-4
• 化学式: C₁₆H₁₂Cl₂N₂O₃
• 分子量: 351.189
• InChiKey: VMLIVXFWHGVZND-UHFFFAOYSA-N

物化性质

• 沸点：
  610.6±55.0 °C(Predicted)
• 密度：
  1.418±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 4-(2,4-dichlorophenyl)-2-methyl-7-oxo-5,6-dihydropyrrolo[3,4-b]pyridine-3-carboxylate 在 吡啶 、 甲醇 、 锂硼氢 、 copper diacetate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成
  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：

  4-(2,4-dichlorobenzylidene)-1-(4-methoxybenzyl)pyrrolidine-2,3-dione 在 ammonium cerium (IV) nitrate 、 硝酸 、 溶剂黄146 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 生成 Methyl 4-(2,4-dichlorophenyl)-2-methyl-7-oxo-5,6-dihydropyrrolo[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
• 7-Oxopyrrolopyridine-derived DPP4 inhibitors—mitigation of CYP and hERG liabilities via introduction of polar functionalities in the active site
  作者：Wei Wang、Pratik Devasthale、Aiying Wang、Tom Harrity、Don Egan、Nathan Morgan、Michael Cap、Aberra Fura、Herbert E. Klei、Kevin Kish、Carolyn Weigelt、Lucy Sun、Paul Levesque、Yi-Xin Li、Robert Zahler、Mark S. Kirby、Lawrence G. Hamann

  DOI：10.1016/j.bmcl.2011.09.074

  日期：2011.11

  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.