3,5-Dichloro-4-[2,5-dimethyl-7-[2-(oxan-4-ylamino)ethylamino]pyrazolo[1,5-a]pyrimidin-3-yl]phenol | 683202-57-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,5-Dichloro-4-[2,5-dimethyl-7-[2-(oxan-4-ylamino)ethylamino]pyrazolo[1,5-a]pyrimidin-3-yl]phenol
• CAS: 683202-57-5
• 化学式: C₂₁H₂₅Cl₂N₅O₂
• 分子量: 450.368
• InChiKey: UUUPYJGZOPAZQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  83.7
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,5-Dichloro-4-[2,5-dimethyl-7-[2-(oxan-4-ylamino)ethylamino]pyrazolo[1,5-a]pyrimidin-3-yl]phenol 、 碘乙烷 在 sodium hydroxide 作用下， 以 水 、 异丙醇 为溶剂， 生成 N-[3-(2,6-dichloro-4-ethoxy-phenyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl]-N'-(tetrahydro-pyran-4-yl)-ethane-1,2-diamine
  参考文献：
  名称：

  Discovery and evaluation of pyrazolo[1,5-a]pyrimidines as neuropeptide Y1 receptor antagonists

  摘要：

  A novel series of pyrazolo[1,5-a]pyrimidine derivatives was synthesized and evaluated as NPY Y1R antagonists. High binding affinity and selectivity were achieved with C3 trisubstituted aryl groups and C7 substituted 2-(tetrahydro-2H-pyran-4-ylamino)ethylamine moieties. Efforts to find close analogs with low plasma clearance in the rat and minimal p-glycoprotein efflux in the mouse were unsuccessful. Compound 2f (CP-671906) inhibited NPY-induced increases in blood pressure and food intake after iv and icv administration, respectively, in Sprague-Dawley (SD) rat models. Oral administration of compound 2f resulted in a modest, but statistically significant, reduction in food intake in a Wistar rat model of feeding behavior. Small inhibitions of food intake were also observed in an overnight fasting/refeeding model in SD rats. These data suggest a potential role for Y1R in the regulation of food intake in rodents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.116
• 作为产物：
  描述：

  N-[3-(2,6-dichloro-4-methoxy-phenyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl]-ethane-1,2-diamine 在 氢溴酸 、 三乙酰氧基硼氢化钠 作用下， 以 水 、 溶剂黄146 为溶剂， 生成 3,5-Dichloro-4-[2,5-dimethyl-7-[2-(oxan-4-ylamino)ethylamino]pyrazolo[1,5-a]pyrimidin-3-yl]phenol
  参考文献：
  名称：

  Discovery and evaluation of pyrazolo[1,5-a]pyrimidines as neuropeptide Y1 receptor antagonists

  摘要：

  A novel series of pyrazolo[1,5-a]pyrimidine derivatives was synthesized and evaluated as NPY Y1R antagonists. High binding affinity and selectivity were achieved with C3 trisubstituted aryl groups and C7 substituted 2-(tetrahydro-2H-pyran-4-ylamino)ethylamine moieties. Efforts to find close analogs with low plasma clearance in the rat and minimal p-glycoprotein efflux in the mouse were unsuccessful. Compound 2f (CP-671906) inhibited NPY-induced increases in blood pressure and food intake after iv and icv administration, respectively, in Sprague-Dawley (SD) rat models. Oral administration of compound 2f resulted in a modest, but statistically significant, reduction in food intake in a Wistar rat model of feeding behavior. Small inhibitions of food intake were also observed in an overnight fasting/refeeding model in SD rats. These data suggest a potential role for Y1R in the regulation of food intake in rodents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.116