1-bromo-3-pyridin-4-yl[2,6]naphthyridine | 1071017-53-2

• 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: 1-bromo-3-pyridin-4-yl[2,6]naphthyridine
• 英文别名: 1-bromo-3-pyridin-4-yl-2,6-naphthyridine
• CAS: 1071017-53-2
• 化学式: C₁₃H₈BrN₃
• 分子量: 286.131
• InChiKey: RWMGFKJSAHBNDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-bromo-3-pyridin-4-yl[2,6]naphthyridine 在 盐酸 、 sodium hydride 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.33h， 生成 1,1-dimethyl-2-(3-pyridin-4-yl-[2,6]naphthyridin-1-yloxy)ethylamine
  参考文献：
  名称：

  WO2008/122614

  摘要：

  公开号：
• 作为产物：
  描述：

  3-hydroxy-3-(pyridin-4-yl)-3,4-dihydro-2,6-naphthyridin-1(2H)-one 在 三溴氧磷 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 6.0h， 生成 1-bromo-3-pyridin-4-yl[2,6]naphthyridine
  参考文献：
  名称：

  Identification of Orally Available Naphthyridine Protein Kinase D Inhibitors

  摘要：

  A novel 2,6-naphthyridine was identified by high throughput screen (HTS) as a dual protein kinase C/D (PKC/PKD) inhibitor. PKD inhibition in the heart was proposed as a potential antihypertrophic mechanism with application as a heart failure therapy. As PKC was previously identified as the immediate upstream activator of PKD, PKD vs PKC selectivity was essential to understand the effect of PKD inhibition in models of cardiac hypertrophy and heart failure. The present study describes the modification of the HTS hit to a series of prototype pan-PKD inhibitors with routine 1000-fold PKD vs PKC selectivity. Example compounds inhibited PKD activity in vitro, in cells, and in vivo following oral administration. Their effects on heart morphology and function are discussed herein.

  DOI：

  10.1021/jm100075z

文献信息

• 2, 6-NAPHTHRIDINE DERIVATIVES
  申请人：van Eis Maurice

  公开号：US20100130469A1

  公开（公告）日：2010-05-27

  The present invention relates to novel organic compounds comprising a naphthyridine which may be mediators of a selective subset of kinases belonging to the AGC kinase family, such as for example PKC, PKD, PKN-1/2, CDK-9, MRCK-beat, PASK, PRKX, ROCK-I/II or mediators of other kinases, the selectivity of which would be depending on the structural variation thereof.

  本发明涉及一种新的有机化合物，包括一种萘啶，它可能是AGC激酶家族的一种选择性亚组的介质，例如PKC，PKD，PKN-1/2，CDK-9，MRCK-beat，PASK，PRKX，ROCK-I/II或其他激酶的介质，其选择性取决于其结构变化。
• 2, 6-NAPHTHYRIDINE DERIVATIVES AS PROTEIN KINASE MODULATORS
  申请人：Novartis AG

  公开号：EP2144908A1

  公开（公告）日：2010-01-20
• [EN] 2, 6-NAPHTHYRIDINE DERIVATIVES AS PROTEIN KINASE MODULATORS<br/>[FR] DERIVES DE 2,6-NAPHTHYRIDINE UTILISES EN TANT QUE MODULATEURS DES PROTEINES KINASES
  申请人：NOVARTIS AG

  公开号：WO2008122614A1

  公开（公告）日：2008-10-16

  [EN] The present invention relates to novel organic compounds comprising a naphthyridine which may be mediators of a selective subset of kinases belonging to the AGC kinase family, such as for example PKC, PKD, PKN-1/2, CDK-9, MRCK-beat, PASK, PRKX, ROCK-I/II or mediators of other kinases, the selectivity of which would be depending on the structural variation thereof.
  [FR] L'invention concerne de nouveaux composés organiques contenant une naphthyridine, pouvant servir de médiateurs d'un sous-ensemble sélectif de kinases appartenant à la famille des kinases AGC, telles que PKC, PKD, PKN-1/2, CDK-9, MRCK-beat, PASK, PRKX, ROCK-I/II, ou de médiateurs d'autres kinases dont la sélectivité dépend de leur variation structurelle.
• WO2008/122614
  申请人：——

  公开号：——

  公开（公告）日：——
• Identification of Orally Available Naphthyridine Protein Kinase D Inhibitors
  作者：Erik L. Meredith、Ophelia Ardayfio、Kimberly Beattie、Markus R. Dobler、Istvan Enyedy、Christoph Gaul、Vinayak Hosagrahara、Charles Jewell、Keith Koch、Wendy Lee、HansJoerg Lehmann、Timothy A. McKinsey、Karl Miranda、Nikos Pagratis、Margaret Pancost、Anup Patnaik、Dillon Phan、Craig Plato、Ming Qian、Vasumathy Rajaraman、Chang Rao、Olga Rozhitskaya、Thomas Ruppen、Jie Shi、Sarah J. Siska、Clayton Springer、Maurice van Eis、Richard B. Vega、Anette von Matt、Lihua Yang、Taeyoung Yoon、Ji-Hu Zhang、Na Zhu、Lauren G. Monovich

  DOI：10.1021/jm100075z

  日期：2010.8.12

  A novel 2,6-naphthyridine was identified by high throughput screen (HTS) as a dual protein kinase C/D (PKC/PKD) inhibitor. PKD inhibition in the heart was proposed as a potential antihypertrophic mechanism with application as a heart failure therapy. As PKC was previously identified as the immediate upstream activator of PKD, PKD vs PKC selectivity was essential to understand the effect of PKD inhibition in models of cardiac hypertrophy and heart failure. The present study describes the modification of the HTS hit to a series of prototype pan-PKD inhibitors with routine 1000-fold PKD vs PKC selectivity. Example compounds inhibited PKD activity in vitro, in cells, and in vivo following oral administration. Their effects on heart morphology and function are discussed herein.