(NE)-N-[[4-amino-6-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]pyrimidin-5-yl]methylidene]hydroxylamine | 919485-84-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (NE)-N-[[4-amino-6-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]pyrimidin-5-yl]methylidene]hydroxylamine
• CAS: 919485-84-0
• 化学式: C₁₄H₁₂FN₅O₂
• 分子量: 301.28
• InChiKey: SIALLQRYFKSGBD-PTXOJBNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (NE)-N-[[4-amino-6-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]pyrimidin-5-yl]methylidene]hydroxylamine 、 1-溴-3-甲氧基丙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-5-[(1E)-[(3-methoxypropoxy)imino]methyl]pyrimidin-4-amine
  参考文献：
  名称：

  Synthesis and biological study of 4-aminopyrimidine-5-carboxaldehyde oximes as antiproliferative VEGFR-2 inhibitors

  摘要：

  A novel 4-aminopyrimidine-5-carboxaldehyde oxime scaffold with inhibitory activity against VEGFR-2 kinase has been identified. With a 4-fluoro-2-methylindol-5-yloxy group at the 6-position and alkyl groups as the oxime side chains, many analogues showed good potency for VEGFR-2. This series also exhibited antiproliferative activity against cancer cells, causing cell accumulation at the G2/M phase of the cell cycle and preventing cells from entering mitosis. Described here are the chemistry, structure-activity relationships (SAR), and biological testing for this series.

  DOI：

  10.1016/j.bmcl.2006.08.107
• 作为产物：
  描述：

  4-氨基-6-氯-5-醛基嘧啶 在 盐酸羟胺 、 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 生成 (NE)-N-[[4-amino-6-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]pyrimidin-5-yl]methylidene]hydroxylamine
  参考文献：
  名称：

  Synthesis and biological study of 4-aminopyrimidine-5-carboxaldehyde oximes as antiproliferative VEGFR-2 inhibitors

  摘要：

  A novel 4-aminopyrimidine-5-carboxaldehyde oxime scaffold with inhibitory activity against VEGFR-2 kinase has been identified. With a 4-fluoro-2-methylindol-5-yloxy group at the 6-position and alkyl groups as the oxime side chains, many analogues showed good potency for VEGFR-2. This series also exhibited antiproliferative activity against cancer cells, causing cell accumulation at the G2/M phase of the cell cycle and preventing cells from entering mitosis. Described here are the chemistry, structure-activity relationships (SAR), and biological testing for this series.

  DOI：

  10.1016/j.bmcl.2006.08.107

文献信息

• SUBSTITUTED PYRIMIDINE KINASE INHIBITORS
  申请人：Butler Jeannene

  公开号：US20070254896A1

  公开（公告）日：2007-11-01

  The present invention is directed to substituted pyrimidine compounds of formula (I): and forms thereof, their synthesis and use for treating a chronic or acute protein kinase mediated disease, disorder or condition.

  本发明涉及式(I)的取代嘧啶化合物及其形式，它们的合成和用于治疗慢性或急性蛋白激酶介导的疾病、紊乱或状况。
• US8013153B2
  申请人：——

  公开号：US8013153B2

  公开（公告）日：2011-09-06
• [EN] SUBSTITUTED PYRIMIDINE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE PYRIMIDINE KINASE SUBSTITUEE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2007109783A2

  公开（公告）日：2007-09-27

  [EN] The present invention is directed to substituted pyrimidine compounds of formula (I): and forms thereof, their synthesis and use for treating a chronic or acute protein kinase mediated disease, disorder or condition.
  [FR] La présente invention concerne des composés de pyrimidine substituée de formule (I) : et leurs formes, leur synthèse et leur utilisation dans le traitement d'une maladie, d'une affection ou d'une pathologie chronique ou aiguë induite par une protéine-kinase.
• Synthesis and biological study of 4-aminopyrimidine-5-carboxaldehyde oximes as antiproliferative VEGFR-2 inhibitors
  作者：Shenlin Huang、Ronghua Li、Peter J. Connolly、Guozhang Xu、Michael D. Gaul、Stuart L. Emanuel、Kenneth R. LaMontagne、Lee M. Greenberger

  DOI：10.1016/j.bmcl.2006.08.107

  日期：2006.12

  A novel 4-aminopyrimidine-5-carboxaldehyde oxime scaffold with inhibitory activity against VEGFR-2 kinase has been identified. With a 4-fluoro-2-methylindol-5-yloxy group at the 6-position and alkyl groups as the oxime side chains, many analogues showed good potency for VEGFR-2. This series also exhibited antiproliferative activity against cancer cells, causing cell accumulation at the G2/M phase of the cell cycle and preventing cells from entering mitosis. Described here are the chemistry, structure-activity relationships (SAR), and biological testing for this series.