4-氨基-6-(1H-吲哚-5-氧基)嘧啶-5-甲醛 | 919485-89-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-氨基-6-(1H-吲哚-5-氧基)嘧啶-5-甲醛
• 英文名称: 4-Amino-6-(1H-indol-5-yloxy)-pyrimidine-5-carbaldehyde
• 英文别名: 4-Amino-6-[(1H-indol-5-yl)oxy]pyrimidine-5-carbaldehyde；4-amino-6-(1H-indol-5-yloxy)pyrimidine-5-carbaldehyde
• CAS: 919485-89-5
• 化学式: C₁₃H₁₀N₄O₂
• 分子量: 254.248
• InChiKey: ODITUHSKCJEGBP-UHFFFAOYSA-N

物化性质

• 沸点：
  522.3±50.0 °C(Predicted)
• 密度：
  1.470±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-氨基-6-(1H-吲哚-5-氧基)嘧啶-5-甲醛 、 甲氧基胺盐酸盐 以 二甲基亚砜 为溶剂， 生成 6-(1H-indol-5-yloxy)-5-[(1E)-(methoxyimino)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：

  5-羟基吲哚 、 4-氨基-6-氯-5-醛基嘧啶 在 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 生成 4-氨基-6-(1H-吲哚-5-氧基)嘧啶-5-甲醛
  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

• 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.