6-[4-(4-Methylpiperazin-1-yl)phenyl]-3-phenylpyrazolo[1,5-a]pyrimidine | 1435615-74-9

• 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: 6-[4-(4-Methylpiperazin-1-yl)phenyl]-3-phenylpyrazolo[1,5-a]pyrimidine
• CAS: 1435615-74-9
• 化学式: C₂₃H₂₃N₅
• 分子量: 369.469
• InChiKey: CRGMZDXJWHXPDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-溴-吡唑[1,5-a]咪唑 在 potassium phosphate 、 N-碘代丁二酰亚胺 、 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 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 6-[4-(4-Methylpiperazin-1-yl)phenyl]-3-phenylpyrazolo[1,5-a]pyrimidine
  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.