2-[1,3,5-trimethyl-1-H-pyrazolo[4,3-d]pyrimidin-7-yl]amino-1-butanol | 111770-30-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 2-[1,3,5-trimethyl-1-H-pyrazolo[4,3-d]pyrimidin-7-yl]amino-1-butanol
• 英文别名: 2-[(1,3,5-trimethylpyrazolo[4,3-d]pyrimidin-7-yl)amino]butan-1-ol
• CAS: 111770-30-0
• 化学式: C₁₂H₁₉N₅O
• 分子量: 249.316
• InChiKey: JCBBEMOZAPQKDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  75.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[1,3,5-trimethyl-1-H-pyrazolo[4,3-d]pyrimidin-7-yl]amino-1-butanol 在 三氯氧磷 作用下， 以70%的产率得到CI 943
  参考文献：
  名称：

  Synthesis and potential antipsychotic activity of 1H-imidazo[1,2-c]pyrazolo[3,4-e]pyrimidines

  摘要：

  The synthesis of a series of 1H-imidazo[1,2-c]pyrazolo[3,4-e]pyrimidines is reported along with the effects of these compounds in preclinical tests for antipsychotic activity. Certain of these compounds displayed antipsychotic-like effects in conditioned avoidance tests, but unlike currently used antipsychotic drugs, they did not have affinity for brain dopamine receptors. These compounds also did not cause dystonias predictive of extrapyramidal side effects in monkeys at doses that produced behavioral effects. On the basis of this unique biological profile, a member of this series 7,8-dihydro-8-ethyl-1,3,5-trimethyl-1H-imidao[1,2-c]pyrazol[3,4-e] pyrimidine (19, CI-943), has been selected for clinical evaluation as an antipsychotic agent.

  DOI：

  10.1021/jm00397a032
• 作为产物：
  描述：

  2,5-二甲基-4-硝基吡唑-3-甲酰胺 在 盐酸 、 sodium hydroxide 、 五氯化磷 、 铁粉 、 三乙胺 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 13.5h， 生成 2-[1,3,5-trimethyl-1-H-pyrazolo[4,3-d]pyrimidin-7-yl]amino-1-butanol
  参考文献：
  名称：

  Synthesis and potential antipsychotic activity of 1H-imidazo[1,2-c]pyrazolo[3,4-e]pyrimidines

  摘要：

  The synthesis of a series of 1H-imidazo[1,2-c]pyrazolo[3,4-e]pyrimidines is reported along with the effects of these compounds in preclinical tests for antipsychotic activity. Certain of these compounds displayed antipsychotic-like effects in conditioned avoidance tests, but unlike currently used antipsychotic drugs, they did not have affinity for brain dopamine receptors. These compounds also did not cause dystonias predictive of extrapyramidal side effects in monkeys at doses that produced behavioral effects. On the basis of this unique biological profile, a member of this series 7,8-dihydro-8-ethyl-1,3,5-trimethyl-1H-imidao[1,2-c]pyrazol[3,4-e] pyrimidine (19, CI-943), has been selected for clinical evaluation as an antipsychotic agent.

  DOI：

  10.1021/jm00397a032

文献信息

• Alkylimidazo[1,2-c]pyrazolo[3,4-e]pyrimidines
  申请人：Warner-Lambert Company

  公开号：US04469868A1

  公开（公告）日：1984-09-04

  Alkylimidazo[1,2-c]pyrazolo[3,4-e]pyrimidines and pharmaceutically acceptable salts are described. These compounds are antipsychotic agents. Methods for their preparation, pharmaceutical compositions which contain them and methods for using said compositions are also described.

  描述了烷基咪唑[1,2-c]吡唑并[3,4-e]嘧啶以及药学上可接受的盐。这些化合物是抗精神病药物。还描述了它们的制备方法、含有它们的制药组合物以及使用这些组合物的方法。
• DEWALD, HORACE A.;BEESON, NICHOLAS W.;HERSHENSON, FRED M.;WISE, LAWRENCE +, J. MED. CHEM., 31,(1988) N 2, 454-461
  作者：DEWALD, HORACE A.、BEESON, NICHOLAS W.、HERSHENSON, FRED M.、WISE, LAWRENCE +

  DOI：——

  日期：——
• Synthesis and potential antipsychotic activity of 1H-imidazo[1,2-c]pyrazolo[3,4-e]pyrimidines
  作者：Horace A. DeWald、Nicholas W. Beeson、Fred M. Hershenson、Lawrence D. Wise、David A. Downs、Thomas G. Heffner、Linda L. Coughenour、Thomas A. Pugsley

  DOI：10.1021/jm00397a032

  日期：1988.2

  The synthesis of a series of 1H-imidazo[1,2-c]pyrazolo[3,4-e]pyrimidines is reported along with the effects of these compounds in preclinical tests for antipsychotic activity. Certain of these compounds displayed antipsychotic-like effects in conditioned avoidance tests, but unlike currently used antipsychotic drugs, they did not have affinity for brain dopamine receptors. These compounds also did not cause dystonias predictive of extrapyramidal side effects in monkeys at doses that produced behavioral effects. On the basis of this unique biological profile, a member of this series 7,8-dihydro-8-ethyl-1,3,5-trimethyl-1H-imidao[1,2-c]pyrazol[3,4-e] pyrimidine (19, CI-943), has been selected for clinical evaluation as an antipsychotic agent.