4-(4-methoxy-1-(triisopropylsilyl)-1H-indol-3-yl)pyrimidin-2-amine | 1342253-46-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-(4-methoxy-1-(triisopropylsilyl)-1H-indol-3-yl)pyrimidin-2-amine
• CAS: 1342253-46-6
• 化学式: C₂₂H₃₂N₄OSi
• 分子量: 396.608
• InChiKey: GEKNKQOCLVFYJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.71
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  65.96
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-(4-methoxy-1-(triisopropylsilyl)-1H-indol-3-yl)pyrimidin-2-amine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以90%的产率得到2-amino-4-(4-methoxy-1H-indol-3-yl)pyrimidine
  参考文献：
  名称：

  CNS and antimalarial activity of synthetic meridianin and psammopemmin analogs

  摘要：

  The marine invertebrate-derived meridianin A. the originally proposed structure for psammopemmin A. and several related 3-pyrimidylindole analogs were synthesized and subsequently investigated for central nervous system, antimalarial, and cytotoxic activity. A Suzuki coupling of an indoleborate ester to the pyrimidine electrophile was utilized to form the natural product and derivatives thereof. The 3-pyrimidineindoles were found to prevent radioligand binding to several CNS receptors and transporters, most notably, serotonin receptors (<0.2 mu M K-i for 5HT(2B)). Two compounds also inhibited the human malaria parasite Plasmodium falciparum (IC50 <50 mu M). Only the natural product was cytotoxic toward A549 cells (IC50 = 15 mu M). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.033
• 作为产物：
  描述：

  4-羟基吲哚 在 四(三苯基膦)钯 、 正丁基锂 、 叔丁基锂 、 sodium carbonate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 、 正戊烷 、 苯 为溶剂， 反应 31.25h， 生成 4-(4-methoxy-1-(triisopropylsilyl)-1H-indol-3-yl)pyrimidin-2-amine
  参考文献：
  名称：

  CNS and antimalarial activity of synthetic meridianin and psammopemmin analogs

  摘要：

  The marine invertebrate-derived meridianin A. the originally proposed structure for psammopemmin A. and several related 3-pyrimidylindole analogs were synthesized and subsequently investigated for central nervous system, antimalarial, and cytotoxic activity. A Suzuki coupling of an indoleborate ester to the pyrimidine electrophile was utilized to form the natural product and derivatives thereof. The 3-pyrimidineindoles were found to prevent radioligand binding to several CNS receptors and transporters, most notably, serotonin receptors (<0.2 mu M K-i for 5HT(2B)). Two compounds also inhibited the human malaria parasite Plasmodium falciparum (IC50 <50 mu M). Only the natural product was cytotoxic toward A549 cells (IC50 = 15 mu M). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.033