2-氧代-3-(2-溴-6-硝基苯基)丙酸乙酯 | 608510-29-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氧代-3-(2-溴-6-硝基苯基)丙酸乙酯
• 英文名称: ethyl 3-(2-bromo-6-nitrophenyl)-2-oxopropanoate
• 英文别名: Ethyl 3-(2-Bromo-6-nitrophenyl)-2-oxopropanoate
• CAS: 608510-29-8
• 化学式: C₁₁H₁₀BrNO₅
• 分子量: 316.108
• InChiKey: PMPDZGIUYJJZHL-UHFFFAOYSA-N

物化性质

• 沸点：
  404.2±35.0 °C(Predicted)
• 密度：
  1.577±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氧代-3-(2-溴-6-硝基苯基)丙酸乙酯 在 盐酸 、 硫酸 、 氨 、 三甲基铝 、 iron(II) sulfate 作用下， 生成 4-bromo-2-(4,5-dihydro-1H-imidazol-2-yl)-1-methyl-2,3-dihydroindole
  参考文献：
  名称：

  Indoline analogs of idazoxan: potent .alpha.2-antagonists and .alpha.1-agonists

  摘要：

  The synthesis and alpha-adrenergic activity of a series of substituted 2-imidazolinylindolines are described. Substitution in the indoline ring generated compounds with a spectrum of adrenoceptor antagonist/agonist profiles that proved sensitive to both the nature and position of the substituent. Many of the derivatives possess greater presynaptic antagonist potency than the corresponding benzodioxan 1, dihydrobenzofuran 2, and indan 3 analogues; however, this alpha 2-antagonism is often accompanied by alpha 1-agonist activity. It was not possible to separate alpha 2-antagonist from alpha 1-agonist properties in this series. Compounds of most interest proved to be the N-ethyl 6, 5-chloro-N-methyl 18, and 5-chloro-N-ethyl 23 derivatives, all being potent alpha 2-antagonists and alpha 1-agonists. Substitution at the 4- and 7-position of the indoline ring generally gave compounds with nonselective agonist properties.

  DOI：

  10.1021/jm00400a009
• 作为产物：
  描述：

  2-溴-6-硝基甲苯 、 草酸二乙酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到2-氧代-3-(2-溴-6-硝基苯基)丙酸乙酯
  参考文献：
  名称：

  7和15-癸基苯甲内酯-V8对蛋白激酶C同工酶C1域的合成及结合选择性。

  摘要：

  苯甲内酯-V8（4）是人工肿瘤启动子苯并内酰胺-V8（1）的内酯类似物。为了研究4位7和15上的疏水取代基对蛋白激酶C（PKC）同工酶的结合选择性的影响，合成了7-和15-癸基苯甲内酯-V8（7，8）以及它们对合成PKC同工酶C1的结合亲和力检查肽。化合物8对类似于9-癸基苯甲内酯-V8（5）的新型PKC同工酶显示出中等选择性，而7则选择性较低。与8-癸基苯并内酯-V8不同，化合物7和8在新型PKC同工酶中没有显示出明显的选择性（6）。这些结果表明，在4的8位上引入疏水取代基最有效地开发了PKCε-和PKCeta-选择性粘合剂。

  DOI：

  10.1016/s0960-894x(03)00637-1

文献信息

• Improved synthetic route for the GluN2-specific NMDA receptor glycine site agonist AICP
  作者：Fabao Zhao、Nirvan Rouzbeh、Kasper B. Hansen、Rasmus P. Clausen

  DOI：10.1016/j.tetlet.2020.151653

  日期：2020.3

  for the amino acid moiety, which can be widely used in the synthesis of other amino acid ligands. Further functional evaluation of AICP at the different ionotropic glutamate receptor (iGluR) classes demonstrates that high affinity binding of AICP to the orthosteric binding site is selective for NMDA receptors over AMPA and kainate receptors. Furthermore, high affinity binding of AICP is not observed

  （R）-2-氨基-3-（4-（2-乙基苯基）-1H-吲哚-2-羧酰胺基）丙酸（AICP）是N-甲基-d-天冬氨酸（NMDA）受体甘氨酸位点激动剂，在低纳摩尔范围内具有空前的高效力，并且在效力和激动剂功效方面均具有GluN2亚基依赖性药理作用[1]。在这里，我们报告了一种适用于AICP的可扩展，实用且具有成本效益的合成路线，与之前报道的路线相比，这是一种改进。这种改进的合成路线包括对氨基酸部分的通用二苯甲基酯（DPM）保护，可广泛用于合成其他氨基酸配体。在不同离子型谷氨酸受体（iGluR）类别上对AICP进行的进一步功能评估表明，AICP与正构结合位点的高亲和力结合对NMDA受体的选择性高于对AMPA和KA酸酯的受体。此外，在GluN3A上未观察到AICP的高亲和力结合，d-丝氨酸。因此，这里描述的新方法可以实现AICP的可扩展合成，用作药理学工具化合物来研究神经元NMDA受体亚型与正常脑功能和疾病的关系。
• Indoline analogs of idazoxan: potent .alpha.2-antagonists and .alpha.1-agonists
  作者：Gay P. Fagan、Christopher B. Chapleo、Anthony C. Lane、Malcolm Myers、Alan G. Roach、Colin F. C. Smith、Michael R. Stillings、Anthony P. Welbourn

  DOI：10.1021/jm00400a009

  日期：1988.5

  The synthesis and alpha-adrenergic activity of a series of substituted 2-imidazolinylindolines are described. Substitution in the indoline ring generated compounds with a spectrum of adrenoceptor antagonist/agonist profiles that proved sensitive to both the nature and position of the substituent. Many of the derivatives possess greater presynaptic antagonist potency than the corresponding benzodioxan 1, dihydrobenzofuran 2, and indan 3 analogues; however, this alpha 2-antagonism is often accompanied by alpha 1-agonist activity. It was not possible to separate alpha 2-antagonist from alpha 1-agonist properties in this series. Compounds of most interest proved to be the N-ethyl 6, 5-chloro-N-methyl 18, and 5-chloro-N-ethyl 23 derivatives, all being potent alpha 2-antagonists and alpha 1-agonists. Substitution at the 4- and 7-position of the indoline ring generally gave compounds with nonselective agonist properties.
• Synthesis and binding selectivity of 7- and 15-decylbenzolactone-V8 for the C1 domains of protein kinase C isozymes
  作者：Yu Nakagawa、Kazuhiro Irie、Nobuhiro Yamanaka、Hajime Ohigashi、Ken-ichiro Tsuda

  DOI：10.1016/s0960-894x(03)00637-1

  日期：2003.9

  lactone analogue of the artificial tumor promoter benzolactam-V8 (1). To investigate the effect of hydrophobic substituents at positions 7 and 15 of 4 on binding selectivity for protein kinase C (PKC) isozymes, 7- and 15-decylbenzolactone-V8 (7, 8) were synthesized and their binding affinities for synthetic PKC isozyme C1 peptides were examined. Compound 8 showed moderate selectivity for novel PKC isozymes

  苯甲内酯-V8（4）是人工肿瘤启动子苯并内酰胺-V8（1）的内酯类似物。为了研究4位7和15上的疏水取代基对蛋白激酶C（PKC）同工酶的结合选择性的影响，合成了7-和15-癸基苯甲内酯-V8（7，8）以及它们对合成PKC同工酶C1的结合亲和力检查肽。化合物8对类似于9-癸基苯甲内酯-V8（5）的新型PKC同工酶显示出中等选择性，而7则选择性较低。与8-癸基苯并内酯-V8不同，化合物7和8在新型PKC同工酶中没有显示出明显的选择性（6）。这些结果表明，在4的8位上引入疏水取代基最有效地开发了PKCε-和PKCeta-选择性粘合剂。