ethyl 1-(4-methoxyphenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazole-3-carboxylate | 1049122-22-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1-(4-methoxyphenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazole-3-carboxylate
• 英文别名: ethyl 1-(4-methoxyphenyl)-5-oxo-4H-1,2,4-triazole-3-carboxylate
• CAS: 1049122-22-6
• 化学式: C₁₂H₁₃N₃O₄
• mdl: MFCD11559318
• 分子量: 263.253
• InChiKey: VBCGUZMHQRXHRQ-UHFFFAOYSA-N

物化性质

• 熔点：
  179 °C(Solv: ethanol (64-17-5))
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  80.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 1-(4-methoxyphenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazole-3-carboxylate 在 ammonium acetate 、 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.75h， 生成 2-(4-hydroxyphenyl)-6-methyl-1,2,4-triazolo[4,3-a]pyrazine-3,8-(2H,7H)-dione
  参考文献：
  名称：

  The 1,2,4-Triazolo[4,3-a]pyrazin-3-one as a Versatile Scaffold for the Design of Potent Adenosine Human Receptor Antagonists. Structural Investigations to Target the A_2A Receptor Subtype

  摘要：

  In this work, we describe the identification of the 1,2,4-triazolo[4,3-a]pyrazin-3-one as a new versatile scaffold for the development of adenosine human (h) receptor antagonists. The new chemotype ensued from a molecular simplification approach applied to our previously reported 1,2,4-triazolo[4,3-a]quinoxalin-1-one series. Hence, a set of novel 8-amino-2-aryl-1,2,4-triazolopyrazin-3-one derivatives, featured by different substituents on the 2-phenyl ring (R) and at position 6 (R-6), was synthesized with the main purpose of targeting the hA(2A) adenosine receptor (AR). Several compounds possessed nanomolar affinity for the hA(2A) AR (K-i = 2.910 nM) and some, very interestingly, also showed high selectivity for the target. One selected potent hA(2A) AR antagonist (12, R = H, R-6 = 4-methoxyphenyl) demonstrated some ability to counteract MPP+-induced neurotoxicity in cultured human neuroblastoma SH-SY5Y cells, a widely used in vitro Parkinsons disease model. Docking studies at hAR structures were performed to rationalize the observed affinity data.

  DOI：

  10.1021/acs.jmedchem.7b00457
• 作为产物：
  描述：

  [(4-甲氧基苯基)肼基]氯乙酸乙酯 在 氨 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 4.0h， 生成 ethyl 1-(4-methoxyphenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazole-3-carboxylate
  参考文献：
  名称：

  The 1,2,4-Triazolo[4,3-a]pyrazin-3-one as a Versatile Scaffold for the Design of Potent Adenosine Human Receptor Antagonists. Structural Investigations to Target the A_2A Receptor Subtype

  摘要：

  In this work, we describe the identification of the 1,2,4-triazolo[4,3-a]pyrazin-3-one as a new versatile scaffold for the development of adenosine human (h) receptor antagonists. The new chemotype ensued from a molecular simplification approach applied to our previously reported 1,2,4-triazolo[4,3-a]quinoxalin-1-one series. Hence, a set of novel 8-amino-2-aryl-1,2,4-triazolopyrazin-3-one derivatives, featured by different substituents on the 2-phenyl ring (R) and at position 6 (R-6), was synthesized with the main purpose of targeting the hA(2A) adenosine receptor (AR). Several compounds possessed nanomolar affinity for the hA(2A) AR (K-i = 2.910 nM) and some, very interestingly, also showed high selectivity for the target. One selected potent hA(2A) AR antagonist (12, R = H, R-6 = 4-methoxyphenyl) demonstrated some ability to counteract MPP+-induced neurotoxicity in cultured human neuroblastoma SH-SY5Y cells, a widely used in vitro Parkinsons disease model. Docking studies at hAR structures were performed to rationalize the observed affinity data.

  DOI：

  10.1021/acs.jmedchem.7b00457

文献信息

• A New Method for the Synthesis of 1-Aryl-1,2,4-triazole Derivatives
  作者：Mykola Obushak、Vasyl Matiychuk、Mykhaylo Potopnyk、Roman Luboradzki

  DOI：10.1055/s-0030-1260026

  日期：2011.6

  A new and convenient one-step recyclization method for the synthesis of ethyl 1-aryl-5-oxo-4,5-dihydro-1H-1,2,4-triazole-3-carboxylates is reported. Various ethyl chloro(2-arylhydrazinylidene)ethanoates react with thiazolidine-2,4-dione in the presence of potassium hydroxide to produce the 1-aryl-1,2,4-triazole derivatives in moderate to good yields. The procedure is economical, environmentally friendly

  报道了一种新的方便的一步回收方法，用于合成1-芳基-5-氧代-4，5-二氢-1 H -1,2,4-三唑-3-羧酸乙酯。在氢氧化钾存在下，各种氯（2-芳基肼基亚乙基）乙基乙酯与噻唑烷-2,4-二酮反应，以中等至良好的产率产生1-芳基-1,2,4-三唑衍生物。该程序经济，环保且易于执行。 1,2,4-三唑-重氮盐-开环-噻唑烷-2,4-二酮-杂环化