N,2,5-trimethyl-3-phenyl-N-(pyridin-2-ylmethyl)pyrazolo[1,5-a]pyrimidin-7-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N,2,5-trimethyl-3-phenyl-N-(pyridin-2-ylmethyl)pyrazolo[1,5-a]pyrimidin-7-amine
• 英文别名: N,2,5-trimethyl-3-phenyl-N-(2-pyridylmethyl)pyrazolo[1,5-a]pyrimidin-7-amine
• 化学式: C₂₁H₂₁N₅
• 分子量: 343.431
• InChiKey: AMTSRWKTRQJCSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-甲基-4-苯基-2H-吡唑-3-胺 在 N,N-二甲基苯胺 、 N,N-二异丙基乙胺 、 三氯化磷 作用下， 以 溶剂黄146 、 异丙醇 、 甲苯 为溶剂， 反应 34.5h， 生成 N,2,5-trimethyl-3-phenyl-N-(pyridin-2-ylmethyl)pyrazolo[1,5-a]pyrimidin-7-amine
  参考文献：
  名称：

  Aminopyrazolo[1,5-a]pyrimidines as potential inhibitors of Mycobacterium tuberculosis: Structure activity relationships and ADME characterization

  摘要：

  Whole-cell high-throughput screening of a diverse SoftFocus library against Mycobacterium tuberculosis (Mtb) generated a novel aminopyrazolo[1,5-a]pyrimidine hit series. The synthesis and structure activity relationship studies identified compounds with potent antimycobacterial activity. The SAR of over 140 compounds shows that the 2-pyridylmethylamine moiety at the C-7 position of the pyrazolopyrimidine scaffold was important for Mtb activity, whereas the C-3 position offered a higher degree of flexibility. The series was also profiled for in vitro cytotoxicity and microsomal metabolic stability as well as physicochemical properties. Consequently liabilities to be addressed in a future lead optimization campaign have been identified. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.10.021

文献信息

• Aminopyrazolo[1,5-a]pyrimidines as potential inhibitors of Mycobacterium tuberculosis: Structure activity relationships and ADME characterization
  作者：Candice Soares de Melo、Tzu-Shean Feng、Renier van der Westhuyzen、Richard K. Gessner、Leslie J. Street、Garreth L. Morgans、Digby F. Warner、Atica Moosa、Krupa Naran、Nina Lawrence、Helena I.M. Boshoff、Clifton E. Barry、C. John Harris、Richard Gordon、Kelly Chibale

  DOI：10.1016/j.bmc.2015.10.021

  日期：2015.11

  Whole-cell high-throughput screening of a diverse SoftFocus library against Mycobacterium tuberculosis (Mtb) generated a novel aminopyrazolo[1,5-a]pyrimidine hit series. The synthesis and structure activity relationship studies identified compounds with potent antimycobacterial activity. The SAR of over 140 compounds shows that the 2-pyridylmethylamine moiety at the C-7 position of the pyrazolopyrimidine scaffold was important for Mtb activity, whereas the C-3 position offered a higher degree of flexibility. The series was also profiled for in vitro cytotoxicity and microsomal metabolic stability as well as physicochemical properties. Consequently liabilities to be addressed in a future lead optimization campaign have been identified. (C) 2015 Elsevier Ltd. All rights reserved.