4,5-bis(methoxycarbonyl)-[2,2'-bipyridine]-1-oxide | 1380521-00-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4,5-bis(methoxycarbonyl)-[2,2'-bipyridine]-1-oxide
• 英文别名: Dimethyl 1-oxido-6-pyridin-2-ylpyridin-1-ium-3,4-dicarboxylate
• CAS: 1380521-00-5
• 化学式: C₁₄H₁₂N₂O₅
• 分子量: 288.26
• InChiKey: XSVDZMZDKVJIOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  91
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,5-bis(methoxycarbonyl)-[2,2'-bipyridine]-1-oxide 、 [(9aneS₃)Ru(dmso)₃](PF₆)₂ 以 甲醇 为溶剂， 以81.4%的产率得到fac-(1,4,7-trithiacyclononane)-(dimethylsulfoxide-S)-(4,5-bis(methoxycarbonyl)-[2,2'-bipyridine]-1-oxide)-ruthenium(II) bis(hexafluorophosphate)
  参考文献：
  名称：

  Ruthenium complexes as inhibitors of 15-lipoxygenase-1

  摘要：

  Lipoxygenases metabolize polyunsaturated fatty acids into signalling molecules such as leukotrienes and lipoxins, which play a regulatory role in several inflammatory lung diseases such as asthma, chronic obstructive pulmonary disease (COPD) and chronic bronchitis. Human 15-lipoxygenase-1 (15-LOX-1) is an important mammalian lipoxygenase and plays a crucial role in the biosynthesis of these inflammatory signalling molecules. New classes of inhibitors are needed to explore the lipoxygenases as therapeutic targets. Here, we present the first study that identifies ruthenium(II) (Ru(II)) complexes as novel inhibitors of 15-LOX-1. Our study includes two novel Ru(II) complexes (C1a and C1b), bearing the sulfur macrocycle [9]aneS(3), S-bonded dimethylsulfoxide (dmso-S), and chelate N,N- or N,O-donor ligands which were characterised by high-resolution NMR spectroscopy, X-ray crystallography and other standard physicochemical methods. These novel complexes and previously described Ru(II) complexes with the general formula [(eta(6)-p-cymene)RuCl(O,O-ligand)]CI were tested for inhibition of 15-LOX-1. This enabled identification of Ru(II) complexes that inhibit 15-LOX-1 with a potency in low micromolar range. Enzyme kinetic analysis was also performed, suggesting uncompetitive inhibition. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2015.09.019
• 作为产物：
  描述：

  (2E,3E)-dimethyl 2-((dimethylamino)methylene)-3-(2-oxo-2-(pyridin-2-yl)ethylidene)succinate 在 盐酸羟胺 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以56%的产率得到4,5-bis(methoxycarbonyl)-[2,2'-bipyridine]-1-oxide
  参考文献：
  名称：

  2-取代吡啶-4,5-二羧酸盐及其N-氧化物的简单无金属合成

  摘要：

  在此，由相应的甲基酮简单，无金属地由相应的甲基酮合成2-烷基，2-环烷基，2-芳基和2-杂芳基取代的吡啶3,4-二羧酸酯及其N-氧化物。描述了每种情况下用22个实例证明的收率。该方法补充了2-杂环有机金属试剂的当前偶联反应。

  DOI：

  10.1016/j.tet.2012.04.013