5-(2-bromopyridin-4-yl)-4-cyclopropylpyrimidin-2-amine | 1607817-47-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-(2-bromopyridin-4-yl)-4-cyclopropylpyrimidin-2-amine
• 英文别名: 5-(2-Bromopyridin-4-yl)-4-cyclopropylpyrimidin-2-amine
• CAS: 1607817-47-9
• 化学式: C₁₂H₁₁BrN₄
• 分子量: 291.15
• InChiKey: IODHBHAJJQWZBG-UHFFFAOYSA-N

物化性质

• 沸点：
  484.0±55.0 °C(Predicted)
• 密度：
  1.609±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  64.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-呋喃硼酸 、 5-(2-bromopyridin-4-yl)-4-cyclopropylpyrimidin-2-amine 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 4-cyclopropyl-5-(2-(furan-3-yl)pyridin-4-yl)pyrimidin-2-amine
  参考文献：
  名称：

  Small Molecule that Reverses Dexamethasone Resistance in T-cell Acute Lymphoblastic Leukemia (T-ALL)

  摘要：

  Glucocorticoids are one of the most utilized and effective therapies in treating T-cell acute lymphoblastic leukemia. However, patients often develop resistance to glucocorticoids, rendering these therapies ineffective. We screened 9517 compounds, selected for their lead-like properties, chosen from among 3 372 615 compounds, against a dexamethasone-resistant T-ALL cell line to identify small molecules that reverse glucocorticoid resistance. We synthesized analogues of the most effective compound, termed J9, from the screen in order to define the scaffold's structure activity relationship. Active compounds restored sensitivity to glucocorticoids through upregulation of the glucocorticoid receptor. This compound and mechanism may provide a strategy for overcoming glucocorticoid resistance in patients with T-ALL.

  DOI：

  10.1021/ml500044g
• 作为产物：
  描述：

  2-溴-4-甲基吡啶 在 sodium ethanolate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 18.08h， 生成 5-(2-bromopyridin-4-yl)-4-cyclopropylpyrimidin-2-amine
  参考文献：
  名称：

  Small Molecule that Reverses Dexamethasone Resistance in T-cell Acute Lymphoblastic Leukemia (T-ALL)

  摘要：

  Glucocorticoids are one of the most utilized and effective therapies in treating T-cell acute lymphoblastic leukemia. However, patients often develop resistance to glucocorticoids, rendering these therapies ineffective. We screened 9517 compounds, selected for their lead-like properties, chosen from among 3 372 615 compounds, against a dexamethasone-resistant T-ALL cell line to identify small molecules that reverse glucocorticoid resistance. We synthesized analogues of the most effective compound, termed J9, from the screen in order to define the scaffold's structure activity relationship. Active compounds restored sensitivity to glucocorticoids through upregulation of the glucocorticoid receptor. This compound and mechanism may provide a strategy for overcoming glucocorticoid resistance in patients with T-ALL.

  DOI：

  10.1021/ml500044g

文献信息

• Small Molecule that Reverses Dexamethasone Resistance in T-cell Acute Lymphoblastic Leukemia (T-ALL)
  作者：Alexandra M. Cantley、Matthew Welsch、Alberto Ambesi-Impiombato、Marta Sanchez-Martin、Mi-Yeon Kim、Andras Bauer、Adolfo Ferrando、Brent R. Stockwell

  DOI：10.1021/ml500044g

  日期：2014.7.10

  Glucocorticoids are one of the most utilized and effective therapies in treating T-cell acute lymphoblastic leukemia. However, patients often develop resistance to glucocorticoids, rendering these therapies ineffective. We screened 9517 compounds, selected for their lead-like properties, chosen from among 3 372 615 compounds, against a dexamethasone-resistant T-ALL cell line to identify small molecules that reverse glucocorticoid resistance. We synthesized analogues of the most effective compound, termed J9, from the screen in order to define the scaffold's structure activity relationship. Active compounds restored sensitivity to glucocorticoids through upregulation of the glucocorticoid receptor. This compound and mechanism may provide a strategy for overcoming glucocorticoid resistance in patients with T-ALL.