5-氨基-1-苯乙基吡唑-4-甲酸乙酯 | 252903-25-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氨基-1-苯乙基吡唑-4-甲酸乙酯
• 中文别名: 5-氨基-1-苯乙基吡唑-4-羧酸乙酯
• 英文名称: ethyl 5-amino-1-phenethyl-1H-pyrazole-4-carboxylate
• 英文别名: ethyl 5-amino-1-(2-phenylethyl)-1H-pyrazole-4-carboxylate；5-amino-1-phenethyl-1H-pyrazole-4-carboxylic acid ethyl ester；Ethyl 5-amino-1-phenethylpyrazole-4-carboxylate；ethyl 5-amino-1-(2-phenylethyl)pyrazole-4-carboxylate
• CAS: 252903-25-6
• 化学式: C₁₄H₁₇N₃O₂
• 分子量: 259.308
• InChiKey: RQQNKPOAHSWRAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  5-氨基-1-苯乙基吡唑-4-甲酸乙酯 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 42.17h， 生成 6-(methylthio)-1-(2-phenylethyl)-1,5-dihydro-4H-pyrazolo[3,4-d]-pyrimidin-4-one
  参考文献：
  名称：

  Identification of potent c-Src inhibitors strongly affecting the proliferation of human neuroblastoma cells

  摘要：

  Neuroblastoma (NB) represents the most common extracranial paediatric solid tumor for which no specific FDA-approved treatment is currently available. The tyrosine kinase c-Src has been reported to play an important role in the differentiation, cell-adhesion and survival of NB cells. Starting from dual Src/Abl inhibitors previously found active in NB cell lines (1-3), small modification of the original structures almost abolished the Abl activity with a contemporary improvement of affinity and specificity for cSrc. Among the synthesized compounds, the most potent c-Src inhibitor (10a) showed a very interesting antiproliferative activity in SH-SY5Y cells with an IC50 of 80 nM and a favourable ADME profile. A 3D SAR analysis was also attempted and may guide the design of more potent c-Src inhibitors as potential agents for NB treatment. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.079
• 作为产物：
  描述：

  苯肼,硫酸盐 、 2-氰基-3-乙氧基丙烯酸乙酯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 15.5h， 以67%的产率得到5-氨基-1-苯乙基吡唑-4-甲酸乙酯
  参考文献：
  名称：

  迈克尔平衡模型，控制位点对氨基吡唑类化合物的缩合反应

  摘要：

  提出了迈克尔平衡模型，以提供烷氧基丙烯腈和肼之间的位点选择性吡唑缩合。通过采用动力学或热力学控制条件，可以高选择性地获得两种吡唑异构体。迈克尔中间体的底物范围和鉴定，以及竞争途径，为提出的机械方案提供了支持。桑德迈尔的衍生化作用提供了对完全取代的吡唑的位置选择的途径。

  DOI：

  10.1021/acs.orglett.5b01248

文献信息

• AMINOPYRAZOLE DERIVATIVES, PROCESS FOR THE PREPARATION THEREOF, AND COMPOSITION FOR PREVENTING OR TREATING ISCHEMIC DISEASES CONTAINING THE SAME
  申请人：JUNG Yong-Sam

  公开号：US20100063106A1

  公开（公告）日：2010-03-11

  Provided are aminopyrazole derivatives, a process for the preparation thereof, and a composition for preventing or treating an ischemic disease containing the same. Since the aminopyrazole derivatives of the present invention can reduce an ischemic cell death significantly, they can be effectively used for the prevention and treatment of ischemic diseases mediated by ischemic cell death, or protection of organs.

  提供了氨基吡唑衍生物，其制备方法，以及含有该衍生物的用于预防或治疗缺血性疾病的组合物。由于本发明的氨基吡唑衍生物可以显著减少缺血细胞死亡，因此它们可以有效用于预防和治疗由缺血细胞死亡介导的缺血性疾病，或保护器官。
• Identification of potent c-Src inhibitors strongly affecting the proliferation of human neuroblastoma cells
  作者：Marco Radi、Chiara Brullo、Emmanuele Crespan、Cristina Tintori、Francesca Musumeci、Mariangela Biava、Silvia Schenone、Elena Dreassi、Claudio Zamperini、Giovanni Maga、Dafne Pagano、Adriano Angelucci、Mauro Bologna、Maurizio Botta

  DOI：10.1016/j.bmcl.2011.07.079

  日期：2011.10

  Neuroblastoma (NB) represents the most common extracranial paediatric solid tumor for which no specific FDA-approved treatment is currently available. The tyrosine kinase c-Src has been reported to play an important role in the differentiation, cell-adhesion and survival of NB cells. Starting from dual Src/Abl inhibitors previously found active in NB cell lines (1-3), small modification of the original structures almost abolished the Abl activity with a contemporary improvement of affinity and specificity for cSrc. Among the synthesized compounds, the most potent c-Src inhibitor (10a) showed a very interesting antiproliferative activity in SH-SY5Y cells with an IC50 of 80 nM and a favourable ADME profile. A 3D SAR analysis was also attempted and may guide the design of more potent c-Src inhibitors as potential agents for NB treatment. (C) 2011 Elsevier Ltd. All rights reserved.
• A Michael Equilibration Model To Control Site Selectivity in the Condensation toward Aminopyrazoles
  作者：Daniel R. Fandrick、Sanjit Sanyal、Joseph Kaloko、Jason A. Mulder、Yuwen Wang、Ling Wu、Heewon Lee、Frank Roschangar、Matthias Hoffmann、Chris H. Senanayake

  DOI：10.1021/acs.orglett.5b01248

  日期：2015.6.19

  A Michael equilibration model is presented to provide for site-selective pyrazole condensations between alkoxyacrylonitriles and hydrazines. Both pyrazole isomers were accessed with high selectivity by employment of kinetically or thermodynamically controlled conditions. Substrate scope and identification of Michael intermediates, as well as competitive pathways, support the presented mechanistic proposal

  提出了迈克尔平衡模型，以提供烷氧基丙烯腈和肼之间的位点选择性吡唑缩合。通过采用动力学或热力学控制条件，可以高选择性地获得两种吡唑异构体。迈克尔中间体的底物范围和鉴定，以及竞争途径，为提出的机械方案提供了支持。桑德迈尔的衍生化作用提供了对完全取代的吡唑的位置选择的途径。