3-amino-4-cyano-1-(2-fluorobenzyl)pyrazole | 154909-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-amino-4-cyano-1-(2-fluorobenzyl)pyrazole
• 英文别名: 3-Amino-1-[(2-fluorophenyl)methyl]pyrazole-4-carbonitrile
• CAS: 154909-83-8
• 化学式: C₁₁H₉FN₄
• 分子量: 216.218
• InChiKey: ZCQCSAFPAAKBOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  67.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-amino-4-cyano-1-(2-fluorobenzyl)pyrazole 在 对甲苯磺酸 作用下， 以 二苯醚 为溶剂， 反应 4.0h， 生成 5-amino-8-(2-fluorobenzyl)-2-(2-furyl)-pyrazolo<4,3-e>-1,2,4-triazolo<1,5-c>pyrimidine
  参考文献：
  名称：

  Synthesis of imidazo[1,2-c]pyrazolo[4,3-e]pyrimidines, pyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidines and 1,2,4-triazolo[5,1-i]purines: new potent adenosine A2 receptor antagonists

  摘要：

  A number of 2- or 4-fluorobenzylderivatives of imidazo[1,2-c]pyrazolo[4,3-e]pyrimidine, pyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidine and 1,2,4-triazolo[5,1-i] purine have been synthesized. The interaction with the adenosine A2 and A1 receptors was evaluated using selected biological assays . The highest degree of activity was displayed by the 5-amino-2-(2-furyl)-7-(or 8-)-fluorobenzyl-pyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidine 13e, f and 18e, f and -3-fluorobenzyl-1-2-4-triazolo[5,1-i] purines 19e, f. The compound 18f was found to be the most potent A2 antagonist in our series with a selectivity similar to that of the reference compound CGS 15943, but with 75-fold more activity in the platelet aggregation model.

  DOI：

  10.1016/0223-5234(93)90087-u
• 作为产物：
  描述：

  3-氨基-4-氰基吡唑 、 邻氟氯苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以49%的产率得到3-amino-4-cyano-1-(2-fluorobenzyl)pyrazole
  参考文献：
  名称：

  Synthesis of imidazo[1,2-c]pyrazolo[4,3-e]pyrimidines, pyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidines and 1,2,4-triazolo[5,1-i]purines: new potent adenosine A2 receptor antagonists

  摘要：

  A number of 2- or 4-fluorobenzylderivatives of imidazo[1,2-c]pyrazolo[4,3-e]pyrimidine, pyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidine and 1,2,4-triazolo[5,1-i] purine have been synthesized. The interaction with the adenosine A2 and A1 receptors was evaluated using selected biological assays . The highest degree of activity was displayed by the 5-amino-2-(2-furyl)-7-(or 8-)-fluorobenzyl-pyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidine 13e, f and 18e, f and -3-fluorobenzyl-1-2-4-triazolo[5,1-i] purines 19e, f. The compound 18f was found to be the most potent A2 antagonist in our series with a selectivity similar to that of the reference compound CGS 15943, but with 75-fold more activity in the platelet aggregation model.

  DOI：

  10.1016/0223-5234(93)90087-u

文献信息

• Synthesis of imidazo[1,2-c]pyrazolo[4,3-e]pyrimidines, pyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidines and 1,2,4-triazolo[5,1-i]purines: new potent adenosine A2 receptor antagonists
  作者：F Gatta、MR Del Giudice、A Borioni、PA Borea、S Dionisotti、E Ongini

  DOI：10.1016/0223-5234(93)90087-u

  日期：1993.1

  A number of 2- or 4-fluorobenzylderivatives of imidazo[1,2-c]pyrazolo[4,3-e]pyrimidine, pyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidine and 1,2,4-triazolo[5,1-i] purine have been synthesized. The interaction with the adenosine A2 and A1 receptors was evaluated using selected biological assays . The highest degree of activity was displayed by the 5-amino-2-(2-furyl)-7-(or 8-)-fluorobenzyl-pyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidine 13e, f and 18e, f and -3-fluorobenzyl-1-2-4-triazolo[5,1-i] purines 19e, f. The compound 18f was found to be the most potent A2 antagonist in our series with a selectivity similar to that of the reference compound CGS 15943, but with 75-fold more activity in the platelet aggregation model.