4-(4-(pyrazolo[1,5-a]pyrimidin-6-yl)phenyl)morpholine | 1435614-94-0

• 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: 4-(4-(pyrazolo[1,5-a]pyrimidin-6-yl)phenyl)morpholine
• 英文别名: 4-(4-Pyrazolo[1,5-a]pyrimidin-6-ylphenyl)morpholine；4-(4-pyrazolo[1,5-a]pyrimidin-6-ylphenyl)morpholine
• CAS: 1435614-94-0
• 化学式: C₁₆H₁₆N₄O
• 分子量: 280.329
• InChiKey: RNGBSHAPBHVXTG-UHFFFAOYSA-N

物化性质

• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-(pyrazolo[1,5-a]pyrimidin-6-yl)phenyl)morpholine 在 N-碘代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以73%的产率得到4-(4-(3-iodopyrazolo[1,5-a]pyrimidin-6-yl)phenyl)morpholine
  参考文献：
  名称：

  Synthesis and structure–activity relationships of a novel and selective bone morphogenetic protein receptor (BMP) inhibitor derived from the pyrazolo[1.5-a]pyrimidine scaffold of Dorsomorphin: The discovery of ML347 as an ALK2 versus ALK3 selective MLPCN probe

  摘要：

  A structure-activity relationship of the 3- and 6-positions of the pyrazolo[1,5-a] pyrimidine scaffold of the known BMP inhibitors dorsomorphin, 1, LDN-193189, 2, and DMH1, 3, led to the identification of a potent and selective compound for ALK2 versus ALK3. The potency contributions of several 3-position substituents were evaluated with subtle structural changes leading to significant changes in potency. From these studies, a novel 5-quinoline molecule was identified and designated an MLPCN probe molecule, ML347, which shows >300-fold selectivity for ALK2 and presents the community with a selective molecular probe for further biological evaluation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.113
• 作为产物：
  描述：

  4-(4-吗啉基)苯硼酸频哪酯 、 6-溴-吡唑[1,5-a]咪唑 在 potassium phosphate 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.5h， 以71%的产率得到4-(4-(pyrazolo[1,5-a]pyrimidin-6-yl)phenyl)morpholine
  参考文献：
  名称：

  Synthesis and structure–activity relationships of a novel and selective bone morphogenetic protein receptor (BMP) inhibitor derived from the pyrazolo[1.5-a]pyrimidine scaffold of Dorsomorphin: The discovery of ML347 as an ALK2 versus ALK3 selective MLPCN probe

  摘要：

  A structure-activity relationship of the 3- and 6-positions of the pyrazolo[1,5-a] pyrimidine scaffold of the known BMP inhibitors dorsomorphin, 1, LDN-193189, 2, and DMH1, 3, led to the identification of a potent and selective compound for ALK2 versus ALK3. The potency contributions of several 3-position substituents were evaluated with subtle structural changes leading to significant changes in potency. From these studies, a novel 5-quinoline molecule was identified and designated an MLPCN probe molecule, ML347, which shows >300-fold selectivity for ALK2 and presents the community with a selective molecular probe for further biological evaluation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.113

文献信息

• Synthesis and structure–activity relationships of a novel and selective bone morphogenetic protein receptor (BMP) inhibitor derived from the pyrazolo[1.5-a]pyrimidine scaffold of Dorsomorphin: The discovery of ML347 as an ALK2 versus ALK3 selective MLPCN probe
  作者：Darren W. Engers、Audrey Y. Frist、Craig W. Lindsley、Charles C. Hong、Corey R. Hopkins

  DOI：10.1016/j.bmcl.2013.03.113

  日期：2013.6

  A structure-activity relationship of the 3- and 6-positions of the pyrazolo[1,5-a] pyrimidine scaffold of the known BMP inhibitors dorsomorphin, 1, LDN-193189, 2, and DMH1, 3, led to the identification of a potent and selective compound for ALK2 versus ALK3. The potency contributions of several 3-position substituents were evaluated with subtle structural changes leading to significant changes in potency. From these studies, a novel 5-quinoline molecule was identified and designated an MLPCN probe molecule, ML347, which shows >300-fold selectivity for ALK2 and presents the community with a selective molecular probe for further biological evaluation. (C) 2013 Elsevier Ltd. All rights reserved.