3,4-dimethyl-N-(4-(4'-oxo-1',4',5',6'-tetrahydrospiro[piperidine-3,7'pyrrolo[3,2-c]pyridine]-2'-yl)pyridin-2-yl)benzamide | 1312814-60-0

• 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: 3,4-dimethyl-N-(4-(4'-oxo-1',4',5',6'-tetrahydrospiro[piperidine-3,7'pyrrolo[3,2-c]pyridine]-2'-yl)pyridin-2-yl)benzamide
• 英文别名: 3,4-dimethyl-N-[4-(4-oxospiro[5,6-dihydro-1H-pyrrolo[3,2-c]pyridine-7,3'-piperidine]-2-yl)pyridin-2-yl]benzamide
• CAS: 1312814-60-0
• 化学式: C₂₅H₂₇N₅O₂
• 分子量: 429.522
• InChiKey: BAYAFUAQZUNFQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  98.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-dimethyl-N-(4-(4'-oxo-1',4',5',6'-tetrahydrospiro[piperidine-3,7'pyrrolo[3,2-c]pyridine]-2'-yl)pyridin-2-yl)benzamide 在 Chiralpack AD-H 作用下， 以 正庚烷 、 异丙醇 为溶剂， 生成 (R)-3,4-dimethyl-N-(4-(4'-oxo-1',4',5',6'-tetrahydrospiro[piperidine-4,7'pyrrolo[3,2-c]pyridine]-2'-yl)pyridin-2-yl)benzamide 、 (R)-3,4-dimethyl-N-(4-(4'-oxo-1',4',5',6'-tetrahydrospiro[piperidine-4,7'pyrrolo[3,2-c]pyridine]-2'-yl)pyridin-2-yl)benzamide
  参考文献：
  名称：

  Novel ATP competitive MK2 inhibitors with potent biochemical and cell-based activity throughout the series

  摘要：

  Optimization of our previously described pyrrolopiperidone series led to the identification of a new benzamide sub-series, which exhibits consistently high potency in biochemical and cell-based assays throughout the series. Strong inhibition of LPS-induced production of the cytokine TNF alpha is coupled to the regulation of HSP27 phosphorylation, indicating that the observed cellular effects result from the inhibition of MK2. X-ray crystallographic and computational analyses provide a rationale for the high potency of the series. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.071
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 生成 3,4-dimethyl-N-(4-(4'-oxo-1',4',5',6'-tetrahydrospiro[piperidine-3,7'pyrrolo[3,2-c]pyridine]-2'-yl)pyridin-2-yl)benzamide
  参考文献：
  名称：

  Novel ATP competitive MK2 inhibitors with potent biochemical and cell-based activity throughout the series

  摘要：

  Optimization of our previously described pyrrolopiperidone series led to the identification of a new benzamide sub-series, which exhibits consistently high potency in biochemical and cell-based assays throughout the series. Strong inhibition of LPS-induced production of the cytokine TNF alpha is coupled to the regulation of HSP27 phosphorylation, indicating that the observed cellular effects result from the inhibition of MK2. X-ray crystallographic and computational analyses provide a rationale for the high potency of the series. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.071

文献信息

• MK2 INHIBITORS
  申请人：Barf Tjeerd Andries

  公开号：US20120245175A1

  公开（公告）日：2012-09-27

  The present invention relates to compounds of general Formula (I) or a pharmaceutically acceptable salt thereof. The compounds can be used in the treatment of immune, autoimmune, inflammatory diseases, cardiovascular diseases, infectious diseases, bone resorption disorders, neurodegenerative diseases or proliferative diseases.

  本发明涉及一般式（I）的化合物或其药学上可接受的盐。这些化合物可用于治疗免疫、自身免疫、炎症性疾病、心血管疾病、传染病、骨吸收紊乱、神经退行性疾病或增殖性疾病。
• US8772286B2
  申请人：——

  公开号：US8772286B2

  公开（公告）日：2014-07-08
• US9102676B2
  申请人：——

  公开号：US9102676B2

  公开（公告）日：2015-08-11
• Novel ATP competitive MK2 inhibitors with potent biochemical and cell-based activity throughout the series
  作者：Arthur Oubrie、Allard Kaptein、Edwin de Zwart、Niels Hoogenboom、Rianne Goorden、Bas van de Kar、Maaike van Hoek、Vera de Kimpe、Ruud van der Heijden、Judith Borsboom、Bert Kazemier、Jeroen de Roos、Michiel Scheffers、Jos Lommerse、Carsten Schultz-Fademrecht、Tjeerd Barf

  DOI：10.1016/j.bmcl.2011.10.071

  日期：2012.1

  Optimization of our previously described pyrrolopiperidone series led to the identification of a new benzamide sub-series, which exhibits consistently high potency in biochemical and cell-based assays throughout the series. Strong inhibition of LPS-induced production of the cytokine TNF alpha is coupled to the regulation of HSP27 phosphorylation, indicating that the observed cellular effects result from the inhibition of MK2. X-ray crystallographic and computational analyses provide a rationale for the high potency of the series. (C) 2011 Elsevier Ltd. All rights reserved.