2-[5,7-dimethyl-2-(4-(prop-2-yn-1-yloxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl]-N,N-diethylacetamide | 1254174-27-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[5,7-dimethyl-2-(4-(prop-2-yn-1-yloxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl]-N,N-diethylacetamide
• 英文别名: 2-[5,7-dimethyl-2-(4-prop-2-ynoxyphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]-N,N-diethylacetamide
• CAS: 1254174-27-0
• 化学式: C₂₃H₂₆N₄O₂
• 分子量: 390.485
• InChiKey: VHENJOBTWCOIPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  59.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  癸硼烷 、 2-[5,7-dimethyl-2-(4-(prop-2-yn-1-yloxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl]-N,N-diethylacetamide 在 acetonitrile 作用下， 以 甲苯 、 乙腈 为溶剂， 以35%的产率得到
  参考文献：
  名称：

  富含硼的吡唑并嘧啶的合成和细胞摄取：利用转运蛋白有效地将硼运入人类神经胶质瘤细胞。

  摘要：

  新的1,2-氯和7,8-氨基甲碳烷基吡唑并嘧啶以高亲和力与转运蛋白（TSPO）结合，为氯碳烷衍生物的独特的两个位点结合提供了第一个证据。富硼化合物还可以比硼中子俘获疗法（BNCT）中使用的临床药物更有效地将硼递送给人神经胶质瘤细胞。

  DOI：

  10.1039/c1cc14587h
• 作为产物：
  描述：

  2-(2-(4-isopropoxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-N,N-diethylacetamide 在 aluminum (III) chloride 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 2-[5,7-dimethyl-2-(4-(prop-2-yn-1-yloxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl]-N,N-diethylacetamide
  参考文献：
  名称：

  A practical, multigram synthesis of the 2-(2-(4-alkoxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide (DPA) class of high affinity translocator protein (TSPO) ligands

  摘要：

  A practical, multigram approach to the 2-(2-(4-alkoxyphenyl)-5,7-dimethylpyrazolo[1,5-alpyrimidin-3-yl)acetamide (DPA) class of ligands targeting the translocator protein (TSPO) is described. This synthetic route offers several improvements over all previously described sequences, including the isolation of intermediates without resort to chromatography. The common precursor to the DPA class of high affinity TSPO ligands, N,N-diethyl-2-(2-(4-hydroxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide, was produced in 40% yield over six steps, and was cleanly alkylated to give multigram quantities of several DPA analogues in 90-96% yield after recrystallization. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.044

文献信息

• Pyrazolo[1,5-a]pyrimidine acetamides: 4-Phenyl alkyl ether derivatives as potent ligands for the 18kDa translocator protein (TSPO)
  作者：Aaron Reynolds、Raphy Hanani、David Hibbs、Annelaure Damont、Eleonora Da Pozzo、Silvia Selleri、Frédéric Dollé、Claudia Martini、Michael Kassiou

  DOI：10.1016/j.bmcl.2010.07.135

  日期：2010.10

  we report the synthesis of four new phenyl alkyl ether derivatives (7, 9–11) of the pyrazolo[1,5-a]pyrimidine acetamide class, all of which showed high binding affinity and selectivity for the TSPO and, in the case of the propyl, propargyl, and butyl ether derivatives, the ability to increase pregnenolone biosynthesis by 80–175% over baseline in rat C6 glioma cells. While these compounds fit our in silico

  此，我们报告的四个新的苯基烷基醚衍生物（合成7，9 - 11）的吡唑并[1,5-一个]嘧啶乙酰胺类，所有这些都显示出高结合亲和力和选择性的TSPO，并且在在丙基，炔丙基和丁基醚衍生物的情况下，大鼠C6胶质瘤细胞中孕烯醇酮生物合成的能力比基线提高80-175％。虽然这些化合物适合我们的计​​算机生成的TSPO结合药效基团，但当前模型无法说明观察到的功能活性。
• Synthesis and cellular uptake of boron-rich pyrazolopyrimidines: exploitation of the translocator protein for the efficient delivery of boron into human glioma cells
  作者：Ellen L. Crossley、Fatiah Issa、Alana M. Scarf、Michael Kassiou、Louis M. Rendina

  DOI：10.1039/c1cc14587h

  日期：——

  1,2-closo- and 7,8-nido-carboranylpyrazolopyrimidines bind to the translocator protein (TSPO) with high affinity, providing the first evidence of a unique two-site binding profile for the closo-carborane derivative. The boron-rich compounds can also deliver boron to human glioma cells far more effectively than clinical agents used in boron neutron capture therapy (BNCT).

  新的1,2-氯和7,8-氨基甲碳烷基吡唑并嘧啶以高亲和力与转运蛋白（TSPO）结合，为氯碳烷衍生物的独特的两个位点结合提供了第一个证据。富硼化合物还可以比硼中子俘获疗法（BNCT）中使用的临床药物更有效地将硼递送给人神经胶质瘤细胞。
• A practical, multigram synthesis of the 2-(2-(4-alkoxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide (DPA) class of high affinity translocator protein (TSPO) ligands
  作者：Samuel D. Banister、Shane M. Wilkinson、Raphy Hanani、Aaron J. Reynolds、David E. Hibbs、Michael Kassiou

  DOI：10.1016/j.tetlet.2012.05.044

  日期：2012.7

  A practical, multigram approach to the 2-(2-(4-alkoxyphenyl)-5,7-dimethylpyrazolo[1,5-alpyrimidin-3-yl)acetamide (DPA) class of ligands targeting the translocator protein (TSPO) is described. This synthetic route offers several improvements over all previously described sequences, including the isolation of intermediates without resort to chromatography. The common precursor to the DPA class of high affinity TSPO ligands, N,N-diethyl-2-(2-(4-hydroxyphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide, was produced in 40% yield over six steps, and was cleanly alkylated to give multigram quantities of several DPA analogues in 90-96% yield after recrystallization. (C) 2012 Elsevier Ltd. All rights reserved.