dimethyl 2,2'-bipyridine-4,5-dicarboxylate | 1380520-82-0

• 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: dimethyl 2,2'-bipyridine-4,5-dicarboxylate
• 英文别名: Dimethyl 6-pyridin-2-ylpyridine-3,4-dicarboxylate
• CAS: 1380520-82-0
• 化学式: C₁₄H₁₂N₂O₄
• 分子量: 272.26
• InChiKey: MYXBJAFKHRKPKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 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：
  78.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 2,2'-bipyridine-4,5-dicarboxylate 、 [(9aneS₃)Ru(dmso)₃](PF₆)₂ 以 甲醇 为溶剂， 以78.9%的产率得到fac-(1,4,7-trithiacyclononane)-(dimethylsulfoxide-S)-(dimethyl [2,2'-bipyridine]-4,5-dicarboxylate)-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 ammonium acetate 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以47%的产率得到dimethyl 2,2'-bipyridine-4,5-dicarboxylate
  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

文献信息

• Silver(<scp>i</scp>) complexes with different pyridine-4,5-dicarboxylate ligands as efficient agents for the control of cow mastitis associated pathogens
  作者：Tina P. Andrejević、Dusan Milivojevic、Biljana Đ. Glišić、Jakob Kljun、Nevena Lj. Stevanović、Sandra Vojnovic、Strahinja Medic、Jasmina Nikodinovic-Runic、Iztok Turel、Miloš I. Djuran

  DOI：10.1039/d0dt00518e

  日期：——

  study, five new silver(i) complexes with different chelating pyridine-4,5-dicarboxylate types of ligands, [Ag(NO3)(py-2py)]n (1), [Ag(NO3)(py-2metz)]n (2), [Ag(CH3CN)(py-2py)]BF4 (3), [Ag(py-2tz)2]BF4 (4) and [Ag(py-2metz)2]BF4 (5), py-2py is dimethyl 2,2'-bipyridine-4,5-dicarboxylate, py-2metz is dimethyl 2-(4-methylthiazol-2-yl)pyridine-4,5-dicarboxylate and py-2tz is dimethyl 2-(thiazol-2-yl)pyridine-4

  导致乳房炎和牛奶质量降低的牛乳房感染是全世界乳业的最大问题之一。不幸的是，由于对常规使用的抗生素具有抗性的病原体的发展，用于治疗牛乳腺炎的治疗选择受到限制。在寻找对牛乳腺炎相关病原体有活性的药物中，在本研究中，有五种新的具有不同螯合吡啶-4,5-二羧酸盐配体类型的银（i）配合物，[Ag（NO3）（py-2py ）] n（1），[Ag（ ）（py-2metz）] n（2），[Ag（CH3CN）（py-2py）] BF4（3），[Ag（py-2tz）2] （ 4）和[Ag（py-2metz）2] （5），py-2py是2,2'-联吡啶-4,5-二羧酸二甲酯，py-2metz是2-（4-甲基噻唑-2-基）二甲基）-4,5-二羧酸吡啶，而py-2tz是2-（噻唑-2-基）吡啶-4,5-二羧酸二甲酯，使用标准生物测定法和临床分离物，从得自患有乳腺炎的母牛的受污染的牛奶样品中合成，结构
• Tailoring copper(<scp>ii</scp>) complexes with pyridine-4,5-dicarboxylate esters for anti-<i>Candida</i> activity
  作者：Tina P. Andrejević、Ivana Aleksic、Marta Počkaj、Jakob Kljun、Dusan Milivojevic、Nevena Lj. Stevanović、Jasmina Nikodinovic-Runic、Iztok Turel、Miloš I. Djuran、Biljana Đ. Glišić

  DOI：10.1039/d0dt04061d

  日期：——

  Five novel copper(II) complexes with pyridine-4,5-dicarboxylate esters as ligands, [Cu(NO3)(py-2tz)(H2O)3]NO3 (1), [Cu(NO3)2(py-2metz)(H2O)] (2), [Cu(NO3)2(py-2py)(H2O)]·H2O (3), [CuCl2(py-2tz)]2 (4) and [CuCl2(py-2metz)]n (5) (py-2tz is dimethyl 2-(thiazol-2-yl)pyridine-4,5-dicarboxylate, py-2metz is dimethyl 2-(4-methylthiazol-2-yl)pyridine-4,5-dicarboxylate and py-2py is dimethyl 2,2′-bipyridine-4

  五种以吡啶-4,5-二羧酸酯为配体的新型铜( II )配合物，[Cu(NO 3 )(py-2tz)(H 2 O) 3 ]NO 3 ( 1 )，[Cu(NO 3 ) 2 (py-2metz)(H 2 O)] ( 2 ), [Cu(NO 3 ) 2 (py-2py)(H 2 O)]·H 2 O ( 3 ), [CuCl 2 (py-2tz)] 2 ( 4 ) 和 [CuCl 2 (py-2metz)] n ( 5) (py-2tz 是 2-(噻唑-2-基)吡啶-4,5-二甲酸二甲酯，py-2metz 是 2-(4-甲基噻唑-2-基)吡啶-4,5-二甲酸二甲酯和 py- 2py 是 2,2'-联吡啶-4,5-二羧酸二甲酯），通过不同的光谱和电化学方法合成和结构表征。这些配合物的结构通过单晶 X 射线衍射分析确定，证实了相应的吡啶-4,5-二羧酸酯通过氮原子与 Cu( II ) 离子的双齿配位模式。针对两种细菌和两种念珠菌物种评估了铜
• Concomitant polymorphism in an organometallic ruthenium(II) complex with an <i>N</i>,<i>N</i>′-donor ligand
  作者：Katja Traven、Iztok Turel、Julia Koziskova、Lukáč Bučinský、Jozef Kožíšek

  DOI：10.1107/s2053229618006654

  日期：2018.6.1

  The simultaneous crystallization of different polymorphs, i.e. concomitant polymorphism, is a phenomenon which, when properly recognized and studied, can provide useful information for a variety of disciplines. It is rare for ruthenium complexes, although it has been observed. In the synthesis of the ruthenium(II) complex chlorido(η⁶-p-cymene)(dimethyl 2,2′-bypyridine-4,5-dicarboxylate-κ² N,N′)ruthenium(II) hexafluoridophosphate, [RuCl(C₁₀H₁₄)(C₁₄H₁₂N₂O₄)]PF₆, concomitant polymorphs were crystallized under the same conditions. The colour of both crystals was orange, but the shapes, as well as the orientation of the p-cymene and methoxycarbonyl groups, were different. The crystal structures of both isomers show approximately the same bond lengths. In the asymmetric unit, there is one cation and one anion. Due to the absence of strong hydrogen bonds, only weak intermolecular interactions were observed. The Hirshfeld surface and two-dimensional fingerprint plots of both isomers satisfactorily explain the difference in the melting points.

  不同多晶型的同时结晶（即伴随多晶型）是一种现象，如果认识和研究得当，可以为各种学科提供有用的信息。这种现象在钌络合物中比较罕见，但也曾被观察到。在合成钌（II）络合物 chlorido(η6-p-cymene)(dimethyl 2,2′-bypyridine-4,5-dicarboxylate-κ2 在相同条件下，结晶出了[RuCl(C10H14)(C14H12N2O4)]PF6（N,N′）六氟磷酸钌(II)。两种晶体的颜色均为橙色，但形状以及对伞花烃基和甲氧基羰基的取向均不同。两种异构体的晶体结构显示出大致相同的键长。在不对称单元中，有一个阳离子和一个阴离子。由于缺乏强氢键，只能观察到微弱的分子间相互作用。两种异构体的 Hirshfeld 表面和二维指纹图都能很好地解释熔点的差异。
• Ruthenium complexes as inhibitors of the aldo–keto reductases AKR1C1–1C3
  作者：Katja Traven、Maša Sinreih、Jure Stojan、Sara Seršen、Jakob Kljun、Jure Bezenšek、Branko Stanovnik、Iztok Turel、Tea Lanišnik Rižner

  DOI：10.1016/j.cbi.2014.11.005

  日期：2015.6

  The human aldo-keto reductases (AKRs) from the 1C subfamily are important targets for the development of new drugs. In this study, we have investigated the possible interactions between the recombinant AKR1C enzymes AKR1C1-AKR1C3 and ruthenium(II) complexes; in particular, we were interested in the potential inhibitory actions. Five novel ruthenium complexes (1a, 1b, 2a, 2b, 2c), two precursor ruthenium compounds (P1, P2), and three ligands (a, b, c) were prepared and included in this study. Two different types of novel ruthenium(II) complexes were synthesized. First, bearing the sulphur macrocycle [9]aneS(3), S-bonded dimethylsulphoxide (dmso-S), and an N,N-donor ligand, with the general formula of [Ru([9]aneS(3))(dmso)(N,N-ligand)](PF6)(2) (1a, 1b), and second, with the general formula of [(eta(6)-p-cymene)RuCl(N,N-ligand)]Cl (2a, 2b, 2c). All of these synthesized compounds were characterized by high-resolution NMR spectroscopy, X-ray crystallography (compounds a, b, c, 1a, 1b) and other standard physicochemical methods. To evaluate the potential inhibitory actions of these compounds on the AKR1C enzymes, we followed enzymatically catalyzed oxidation of the substrate 1-acenaphthenol by NAD(+) in the absence and presence of various micromolar concentrations of the individual compounds. Among 10 compounds, one ruthenium complex (2b) and two precursor ruthenium compounds (P1, P2) inhibited all three AKR1C enzymes, and one ruthenium complex (2a) inhibited only AKR1C3. Ligands a, b and c revealed no inhibition of the AKR1C enzymes. All four of the active compounds showed multiple binding with the AKR1C enzymes that was characterized by an initial instantaneous inhibition followed by a slow quasi-irreversible step. To the best of our knowledge, this is the first study that has examined interactions between these AKR1C enzymes and ruthenium(II) complexes. (C) 2014 Elsevier Ireland Ltd. All rights reserved.