4-(2,4-dichlorophenyl)-3-(hydroxymethyl)-2-methyl-6-phenyl-7H-pyrrolo[3,4-b]pyridin-5-one | 915297-28-8

• 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: 4-(2,4-dichlorophenyl)-3-(hydroxymethyl)-2-methyl-6-phenyl-7H-pyrrolo[3,4-b]pyridin-5-one
• CAS: 915297-28-8
• 化学式: C₂₁H₁₆Cl₂N₂O₂
• 分子量: 399.276
• InChiKey: CNDZWVXCRQVERV-UHFFFAOYSA-N

物化性质

• 沸点：
  616.7±55.0 °C(Predicted)
• 密度：
  1.411±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2,4-dichlorophenyl)-3-(hydroxymethyl)-2-methyl-6-phenyl-7H-pyrrolo[3,4-b]pyridin-5-one 在 氨 、 甲基磺酰氯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 3-(aminomethyl)-4-(2,4-dichlorophenyl)-2-methyl-6-phenyl-6,7-dihydropyrrolo[3,4-b]pyridin-5-one
  参考文献：
  名称：

  Optimization of Activity, Selectivity, and Liability Profiles in 5-Oxopyrrolopyridine DPP4 Inhibitors Leading to Clinical Candidate (Sa)-2-(3-(Aminomethyl)-4-(2,4-dichlorophenyl)-2-methyl-5-oxo-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)-N,N-dimethylacetamide (BMS-767778)

  摘要：

  Optimization of a 5-oxopyrrolopyridine series based upon structure activity relationships (SARs) developed from our previous efforts on a number of related bicyclic series yielded compound 2s (BMS-767778) with an overall activity, selectivity, efficacy, PK, and developability profile suitable for progression into the clinic. SAR in the series and characterization of 2s are described.

  DOI：

  10.1021/jm4008906
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 20.0h， 生成 4-(2,4-dichlorophenyl)-3-(hydroxymethyl)-2-methyl-6-phenyl-7H-pyrrolo[3,4-b]pyridin-5-one
  参考文献：
  名称：

  Optimization of Activity, Selectivity, and Liability Profiles in 5-Oxopyrrolopyridine DPP4 Inhibitors Leading to Clinical Candidate (Sa)-2-(3-(Aminomethyl)-4-(2,4-dichlorophenyl)-2-methyl-5-oxo-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)-N,N-dimethylacetamide (BMS-767778)

  摘要：

  Optimization of a 5-oxopyrrolopyridine series based upon structure activity relationships (SARs) developed from our previous efforts on a number of related bicyclic series yielded compound 2s (BMS-767778) with an overall activity, selectivity, efficacy, PK, and developability profile suitable for progression into the clinic. SAR in the series and characterization of 2s are described.

  DOI：

  10.1021/jm4008906

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
• Optimization of Activity, Selectivity, and Liability Profiles in 5-Oxopyrrolopyridine DPP4 Inhibitors Leading to Clinical Candidate (<i>Sa</i>)-2-(3-(Aminomethyl)-4-(2,4-dichlorophenyl)-2-methyl-5-oxo-5<i>H</i>-pyrrolo[3,4-<i>b</i>]pyridin-6(7<i>H</i>)-yl)-<i>N</i>,<i>N</i>-dimethylacetamide (BMS-767778)
  作者：Pratik Devasthale、Ying Wang、Wei Wang、John Fevig、JianXin Feng、Aiying Wang、Tom Harrity、Don Egan、Nathan Morgan、Michael Cap、Aberra Fura、Herbert E. Klei、Kevin Kish、Carolyn Weigelt、Lucy Sun、Paul Levesque、Frederic Moulin、Yi-Xin Li、Robert Zahler、Mark S. Kirby、Lawrence G. Hamann

  DOI：10.1021/jm4008906

  日期：2013.9.26

  Optimization of a 5-oxopyrrolopyridine series based upon structure activity relationships (SARs) developed from our previous efforts on a number of related bicyclic series yielded compound 2s (BMS-767778) with an overall activity, selectivity, efficacy, PK, and developability profile suitable for progression into the clinic. SAR in the series and characterization of 2s are described.