1-(4-nitro-phenyl)-5-oxo-2,5-dihydro-1H-[1,2,4]triazole-3-carboxylic acid ethyl ester | 959314-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-nitro-phenyl)-5-oxo-2,5-dihydro-1H-[1,2,4]triazole-3-carboxylic acid ethyl ester
• 英文别名: 1-(4-Nitro-phenyl)-5-oxo-2,5-dihydro-1H-[1,2,4]triazol-3-carbonsaeure-aethylester；Ethyl 1-(4-nitrophenyl)-5-oxo-2,5-dihydro-1H-1,2,4-triazole-3-carboxylate；ethyl 1-(4-nitrophenyl)-5-oxo-4H-1,2,4-triazole-3-carboxylate
• CAS: 959314-36-4
• 化学式: C₁₁H₁₀N₄O₅
• 分子量: 278.224
• InChiKey: QECIUJJOADZZFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(4-nitro-phenyl)-5-oxo-2,5-dihydro-1H-[1,2,4]triazole-3-carboxylic acid ethyl ester 在 氢氧化钾 作用下， 生成 1-(4-nitro-phenyl)-5-oxo-2,5-dihydro-1H-[1,2,4]triazole-3-carboxylic acid
  参考文献：
  名称：

  1,2,4-三唑和吡唑的衍生物。

  摘要：

  DOI：

  10.1021/ja01208a018
• 作为产物：
  描述：

  bromo-(4-nitro-phenylhydrazono)-acetic acid ethyl ester 在 吡啶 、 氨 作用下， 生成 1-(4-nitro-phenyl)-5-oxo-2,5-dihydro-1H-[1,2,4]triazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  1,2,4-三唑和吡唑的衍生物。

  摘要：

  DOI：

  10.1021/ja01208a018

文献信息

• The 1,2,4-Triazolo[4,3-<i>a</i>]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
  作者：Matteo Falsini、Lucia Squarcialupi、Daniela Catarzi、Flavia Varano、Marco Betti、Diego Dal Ben、Gabriella Marucci、Michela Buccioni、Rosaria Volpini、Teresa De Vita、Andrea Cavalli、Vittoria Colotta

  DOI：10.1021/acs.jmedchem.7b00457

  日期：2017.7.13

  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.
• Fusco; Musante, Gazzetta Chimica Italiana, 1938, vol. 68, p. 665,675, 676
  作者：Fusco、Musante

  DOI：——

  日期：——