4-(benzo[d][1,3]dioxol-5-yl)pyrimidin-2-amine | 685106-65-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 4-(benzo[d][1,3]dioxol-5-yl)pyrimidin-2-amine
• 英文别名: 4-(1,3-Benzodioxol-5-yl)pyrimidin-2-amine
• CAS: 685106-65-4
• 化学式: C₁₁H₉N₃O₂
• mdl: MFCD03617335
• 分子量: 215.211
• InChiKey: TYPNCFKVEIHZOY-UHFFFAOYSA-N

物化性质

• 沸点：
  473.3±55.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(benzo[d][1,3]dioxol-5-yl)pyrimidin-2-amine 、 3,4-二溴苯甲醛 在 三异丙氧基氯化钛 、 溶剂黄146 、 三乙酰氧基硼氢化钠 作用下， 以 乙腈 为溶剂， 反应 1.08h， 以31%的产率得到4-(benzo[d][1,3]dioxol-5-yl)-N-(3,4-dibromobenzyl)pyrimidin-2-amine
  参考文献：
  名称：

  Small-molecule pyrimidine inhibitors of the cdc2-like (Clk) and dual specificity tyrosine phosphorylation-regulated (Dyrk) kinases: Development of chemical probe ML315

  摘要：

  Substituted pyrimidine inhibitors of the Clk and Dyrk kinases have been developed, exploring structure-activity relationships around four different chemotypes. The most potent compounds have low-nanomolar inhibitory activity against Clk1, Clk2, Clk4, Dyrk1A and Dyrk1B. Kinome scans with 442 kinases using agents representing three of the chemotypes show these inhibitors to be highly selective for the Clk and Dyrk families. Further off-target pharmacological evaluation with ML315, the most selective agent, supports this conclusion. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.096
• 作为产物：
  描述：

  2-氨基-4-氯嘧啶 、 3.4-(亚甲基二氧基)苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 以77%的产率得到4-(benzo[d][1,3]dioxol-5-yl)pyrimidin-2-amine
  参考文献：
  名称：

  Small-molecule pyrimidine inhibitors of the cdc2-like (Clk) and dual specificity tyrosine phosphorylation-regulated (Dyrk) kinases: Development of chemical probe ML315

  摘要：

  Substituted pyrimidine inhibitors of the Clk and Dyrk kinases have been developed, exploring structure-activity relationships around four different chemotypes. The most potent compounds have low-nanomolar inhibitory activity against Clk1, Clk2, Clk4, Dyrk1A and Dyrk1B. Kinome scans with 442 kinases using agents representing three of the chemotypes show these inhibitors to be highly selective for the Clk and Dyrk families. Further off-target pharmacological evaluation with ML315, the most selective agent, supports this conclusion. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.096

文献信息

• Small-molecule pyrimidine inhibitors of the cdc2-like (Clk) and dual specificity tyrosine phosphorylation-regulated (Dyrk) kinases: Development of chemical probe ML315
  作者：Thomas C. Coombs、Cordelle Tanega、Min Shen、Jenna L. Wang、Douglas S. Auld、Samuel W. Gerritz、Frank J. Schoenen、Craig J. Thomas、Jeffrey Aubé

  DOI：10.1016/j.bmcl.2013.02.096

  日期：2013.6

  Substituted pyrimidine inhibitors of the Clk and Dyrk kinases have been developed, exploring structure-activity relationships around four different chemotypes. The most potent compounds have low-nanomolar inhibitory activity against Clk1, Clk2, Clk4, Dyrk1A and Dyrk1B. Kinome scans with 442 kinases using agents representing three of the chemotypes show these inhibitors to be highly selective for the Clk and Dyrk families. Further off-target pharmacological evaluation with ML315, the most selective agent, supports this conclusion. (C) 2013 Elsevier Ltd. All rights reserved.