diethyl 4-amino-1-phenyl-1H-pyrazole-3,5-dicarboxylate | 58838-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: diethyl 4-amino-1-phenyl-1H-pyrazole-3,5-dicarboxylate
• 英文别名: diethyl 4-amino-1-phenylpyrazole-3,5-dicarboxylate
• CAS: 58838-11-2
• 化学式: C₁₅H₁₇N₃O₄
• 分子量: 303.318
• InChiKey: ZUYMVBSMINIVTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  96.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 4-amino-1-phenyl-1H-pyrazole-3,5-dicarboxylate 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以50%的产率得到4-amino-1-phenyl-1H-pyrazole-3,5-dicarboxylic acid
  参考文献：
  名称：

  2-Phenylpyrazolo[4,3-d]pyrimidin-7-one as a New Scaffold To Obtain Potent and Selective Human A₃ Adenosine Receptor Antagonists: New Insights into the Receptor−Antagonist Recognition

  摘要：

  A molecular simplification approach of previously reported 2-arylpyrazolo[3,4-c]quinolin-4-ones was applied to design 2-arylpyrazolo[4,3-d]pyrimidin-7-one derivatives as new human A(3) adenosine receptor antagonists. Substituents with different lipophilicity and steric hindrance were introduced at the 5-position of the bicyclic Scaffold (R-5 = H, Me, Et, Ph, CH2Ph) and on the 2-phenyl ring (OMe, Me). Most of the synthesized derivatives were highly potent hA(3) adenosine receptor antagonists, the best being the 2-(4-methoxyphenyl)pyrazolo[4,3-d]pyrimidin-7-one (K-i = 1.2 nM). The new compounds were also highly selective, being completely devoid of affinity toward hA(1), hA(2A), and hA(2B) adenosine receptors. On the basis of the recently published human A(2A) receptor crystallographic information, we propose it novel receptor-driven hypothesis to explain both A(3) AR affinity and A(3) versus A(2A) Selectivity profiles of these new antagonists.

  DOI：

  10.1021/jm900718w
• 作为产物：
  描述：

  溴乙酸乙酯 、 E-ethyl cyano(phenylhydrazono)acetate 在 氢氧化钾 、 18-冠醚-6 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以81%的产率得到diethyl 4-amino-1-phenyl-1H-pyrazole-3,5-dicarboxylate
  参考文献：
  名称：

  Improved Protocol for Thorpe Reaction: Synthesis of 4‐Amino‐1‐arylpyrazole using Solid–Liquid Phase‐Transfer Conditions

  摘要：

  Solid - liquid phase-transfer conditions were employed for the first time in the Thorpe reaction to synthesize 4-amino-1-aryl-3,5-substituted-1H-pyrazoles 3. Aryl amines were diazotized and coupled with various active methylene compounds such as cyano acetamide, cyanoacetophenone, malononitrile, and ethyl cyanoacetate, resulting into alpha-arylhydrazononitriles 1. Cyclization of 1 using alpha-bromo ketones or esters resulted in compounds 3.

  DOI：

  10.1080/00397910701767023

文献信息

• GEWALD K.; CALDERON O., MONATSH. CHEM. <MOCH-AP>, 1977, 108, NO 3, 611-616
  作者：GEWALD K.、 CALDERON O.

  DOI：——

  日期：——