(E)-1-(6-bromopyridin-3-yl)-3-(dimethylamino)prop-2-en-1-one | 1186334-35-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1-(6-bromopyridin-3-yl)-3-(dimethylamino)prop-2-en-1-one
• 英文别名: (2E)-1-(6-bromopyridin-3-yl)-3-(dimethylamino)prop-2-en-1-one
• CAS: 1186334-35-9
• 化学式: C₁₀H₁₁BrN₂O
• 分子量: 255.114
• InChiKey: CUXBXJXBEZCEQP-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  盐酸胍 、 (E)-1-(6-bromopyridin-3-yl)-3-(dimethylamino)prop-2-en-1-one 在 乙醇 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以58%的产率得到4-(6-bromopyridin-3-yl)pyrimidin-2-amine
  参考文献：
  名称：

  Design and synthesis of new anticancer pyrimidines with multiple-kinase inhibitory effect

  摘要：

  A new series of N-substituted-2-aminopyrimidines based on the '4-(pyridin-3-yl)pyrimidin-2-amine' scaffold of Imatinib has been designed and synthesized. A selected group from the target compounds was tested over a panel of 60 cancer cell lines at a single dose concentration of 10 mu M, and the two most active compounds, 25b and 30, were further tested in a five-dose testing mode to determine their IC50 values over the 60 cell lines. Compound 30 has showed good potencies and high efficacies, and was accordingly tested at a single dose concentration of 10 mu M over a panel of 54 kinases. At this concentration, the compound has showed multiple inhibitions over a number of oncogenic kinases, including ABL1, AKT1, LCK, C-SRC, PIM1, FLT3, FYN, and KDR. A molecular modeling study was made by docking of the most active compound 30 and its inactive analog 29 into the kinase domain of ABL1 to investigate their possible binding interactions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.037
• 作为产物：
  描述：

  5-乙酰基-2-溴吡啶 、 N,N-二甲基甲酰胺二甲基缩醛 在 乙醚 作用下， 反应 18.5h， 以to provide 5.20 g (82% yield) of (2E)-1-(6-bromopyridin-3-yl)-3-(dimethylamino)prop-2-en-1-one, which的产率得到(E)-1-(6-bromopyridin-3-yl)-3-(dimethylamino)prop-2-en-1-one
  参考文献：
  名称：

  Bridged, Bicyclic Heterocyclic or Spiro Bicyclic Heterocyclic Derivatives of Pyrazolo[1, 5-A]Pyrimidines, Methods for Preparation and Uses Thereof

  摘要：

  描述了化学式A的化合物及其药学上可接受的盐，这些化合物可选择性地抑制Raf激酶活性，并用于治疗由Raf激酶介导的疾病。

  公开号：

  US20100029657A1

文献信息

• Compounds for binding and imaging amyloid plaques and their use
  申请人：Röhn Ulrike

  公开号：US20120237446A1

  公开（公告）日：2012-09-20

  The present invention relates to novel compounds (3-aminopropen-1-ones) useful for binding and imaging beta amyloid deposits and their use in detecting or treating Alzheimer's disease and amyloidosis.

  本发明涉及新型化合物（3-氨基丙烯酮），用于结合和成像β淀粉样沉积物，以及它们在检测或治疗阿尔茨海默病和淀粉样病中的应用。
• Bridged, Bicyclic Heterocyclic or Spiro Bicyclic Heterocyclic Derivatives of Pyrazolo[1, 5-A]Pyrimidines, Methods for Preparation and Uses Thereof
  申请人：Levin Jeremy Ian

  公开号：US20100029657A1

  公开（公告）日：2010-02-04

  Compounds of formula A: and pharmaceutically acceptable salts thereof are described, which selectively inhibit Raf kinase activity and are useful for treating disorders mediated by Raf kinases.

  描述了化学式A的化合物及其药学上可接受的盐，这些化合物可选择性地抑制Raf激酶活性，并用于治疗由Raf激酶介导的疾病。
• [EN] BRIDGED, BICYCLIC HETEROCYCLIC OR SPIRO BICYCLIC HETEROCYCLIC DERIVATIVES OF PYRAZOLO[1,5-A]PYRIMIDINES, METHODS FOR PREPARATION AND USES THEREOF<br/>[FR] DÉRIVÉS HÉTÉROCYCLIQUES BICYCLIQUES PONTÉS OU HÉTÉROCYCLIQUES BICYCLIQUES SPIRO DE PYRAZOLO[1,5-A]PYRIMIDINES, LEURS PROCÉDÉS DE PRÉPARATION ET LEURS UTILISATIONS
  申请人：WYETH CORP

  公开号：WO2009108838A8

  公开（公告）日：2009-11-12
• BRIDGED, BICYCLIC HETEROCYCLIC OR SPIRO BICYCLIC HETEROCYCLIC DERIVATIVES OF PYRAZOLO[1,5-A]PYRIMIDINES, METHODS FOR PREPARATION AND USES THEREOF
  申请人：Wyeth LLC

  公开号：EP2271649A1

  公开（公告）日：2011-01-12
• Design and synthesis of new anticancer pyrimidines with multiple-kinase inhibitory effect
  作者：Ibrahim Mustafa El-Deeb、So Ha Lee

  DOI：10.1016/j.bmc.2010.04.037

  日期：2010.6.1

  A new series of N-substituted-2-aminopyrimidines based on the '4-(pyridin-3-yl)pyrimidin-2-amine' scaffold of Imatinib has been designed and synthesized. A selected group from the target compounds was tested over a panel of 60 cancer cell lines at a single dose concentration of 10 mu M, and the two most active compounds, 25b and 30, were further tested in a five-dose testing mode to determine their IC50 values over the 60 cell lines. Compound 30 has showed good potencies and high efficacies, and was accordingly tested at a single dose concentration of 10 mu M over a panel of 54 kinases. At this concentration, the compound has showed multiple inhibitions over a number of oncogenic kinases, including ABL1, AKT1, LCK, C-SRC, PIM1, FLT3, FYN, and KDR. A molecular modeling study was made by docking of the most active compound 30 and its inactive analog 29 into the kinase domain of ABL1 to investigate their possible binding interactions. (C) 2010 Elsevier Ltd. All rights reserved.