7-chloro-2,5-dimethyl-3-phenylpyrazolo[1,5-a]pyrimidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 7-chloro-2,5-dimethyl-3-phenylpyrazolo[1,5-a]pyrimidine
• 化学式: C₁₄H₁₂ClN₃
• mdl: MFCD11982958
• 分子量: 257.722
• InChiKey: JOISBKFSEWNWGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-氨甲基吡啶 、 7-chloro-2,5-dimethyl-3-phenylpyrazolo[1,5-a]pyrimidine 在 N,N-二异丙基乙胺 作用下， 以 异丙醇 为溶剂， 反应 16.0h， 以98%的产率得到2,5-dimethyl-3-phenyl-N-(pyridin-3-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
• 作为产物：
  描述：

  α-苯乙酰乙腈 在 盐酸肼 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 生成 7-chloro-2,5-dimethyl-3-phenylpyrazolo[1,5-a]pyrimidine
  参考文献：
  名称：

  Optimization of 3-phenylpyrazolo[1,5- a ]pyrimidines as potent corticotropin-releasing factor-1 antagonists with adequate lipophilicity and water solubility

  摘要：

  In our efforts to identify potent CRF1 antagonists with proper physicochemical properties, a series of 3-phenylpyrazolo[1,5-a]pyrimidines bearing polar groups, such as amino, hydroxyl, methoxy, sulfoxide, were designed and synthesized. Several positions of the core structure were identified, where a polar group was tolerated with slight reduction in receptor binding. NBI 30545 (18n) was found to have good binding affinity and potent antagonistic activity at the human CRF1 receptor. Moreover, this compound had proper lipophilicity (log D = 2.78) and good solubility in water (>10 mg/mL), and exhibited good plasma and brain exposure when given orally. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.019