5,7-dichloro-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine | 1373519-64-2

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: 5,7-dichloro-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine
• 英文别名: 5,7-Dichloro-2-methyl-[1,2,4]triazolo[1,5-A]pyrimidine
• CAS: 1373519-64-2
• 化学式: C₆H₄Cl₂N₄
• 分子量: 203.031
• InChiKey: JLQBKJYNOAHPBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,7-dichloro-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine 在 potassium carbonate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.92h， 生成 5-chloro-3-(2,3-dichlorobenzyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7(3H)-one
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 1,2,4-triazolo[1,5-a]pyrimidin-7(3H)-ones as novel series of potent β isoform selective phosphatidylinositol 3-kinase inhibitors

  摘要：

  A series of 1,2,4-triazolo[1,5-a]pyrimidin-7(3H)-ones with excellent enzyme inhibition, improved isoform selectivity, and excellent inhibition of downstream phosphorylation of AKT has been identified. Several compounds in the series demonstrated potent (similar to 0.100 mu M IC50) growth inhibition in a PTEN deficient cancer cell line. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.039
• 作为产物：
  描述：

  2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-5,7-diol 在 三氯氧磷 作用下， 反应 12.0h， 以60%的产率得到5,7-dichloro-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidine
  参考文献：
  名称：

  Synthesis and biological evaluation of benzhydryl-based antiplasmodial agents possessing Plasmodium falciparum chloroquine resistance transporter (PfCRT) inhibitory activity

  摘要：

  DOI：

  10.1016/j.ejmech.2021.113227

文献信息

• Synthesis and biological evaluation of benzhydryl-based antiplasmodial agents possessing Plasmodium falciparum chloroquine resistance transporter (PfCRT) inhibitory activity
  作者：Nicola Relitti、Stefano Federico、Luca Pozzetti、Stefania Butini、Stefania Lamponi、Donatella Taramelli、Sarah D’Alessandro、Rowena E. Martin、Sarah H. Shafik、Robert L. Summers、Simone K. Babij、Annette Habluetzel、Sofia Tapanelli、Reto Caldelari、Sandra Gemma、Giuseppe Campiani

  DOI：10.1016/j.ejmech.2021.113227

  日期：2021.4
• Synthesis and structure–activity relationships of 1,2,4-triazolo[1,5-a]pyrimidin-7(3H)-ones as novel series of potent β isoform selective phosphatidylinositol 3-kinase inhibitors
  作者：Robert M. Sanchez、Karl Erhard、Mary Ann Hardwicke、Hong Lin、Jeanelle McSurdy-Freed、Ramona Plant、Kaushik Raha、Cynthia M. Rominger、Michael D. Schaber、Michael D. Spengler、Michael L. Moore、Hongyi Yu、Juan I. Luengo、Rosanna Tedesco、Ralph A. Rivero

  DOI：10.1016/j.bmcl.2012.03.039

  日期：2012.5

  A series of 1,2,4-triazolo[1,5-a]pyrimidin-7(3H)-ones with excellent enzyme inhibition, improved isoform selectivity, and excellent inhibition of downstream phosphorylation of AKT has been identified. Several compounds in the series demonstrated potent (similar to 0.100 mu M IC50) growth inhibition in a PTEN deficient cancer cell line. (C) 2012 Elsevier Ltd. All rights reserved.