2-(2’-pyridyl)pyrimidine-4-carboxylic acid nitric acid adduct | 1094211-78-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-(2’-pyridyl)pyrimidine-4-carboxylic acid nitric acid adduct
• 英文别名: 2-(2'-pyridyl)pyrimidine-4-carboxylic acid - nitric acid (1/1)；2-(2’-pyridyl)pyrimidine-4-carboxylic acid nitrate；2-(pyridin-2-yl)pyrimidine-4-carboxylic acid mononitrate；2-(pyridin-2-yl)pyrimidine-4-carboxylic acid nitrate；cppH*HNO3
• CAS: 1094211-78-5
• 化学式: C₁₀H₇N₃O₂*HNO₃
• 分子量: 264.197
• InChiKey: KGVGKWYHEVQLFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  139.34
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(2’-pyridyl)pyrimidine-4-carboxylic acid nitric acid adduct 在 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 34.0h， 生成 6-(2-(pyridin-2-yl)pyrimidine-4-carboxamido)hexanoic acid
  参考文献：
  名称：

  功能化的钌（II）吡啶基配合物的合成，光谱性质和光诱导的CO释放研究：开发CORM-肽核酸生物共轭物的多功能构建基块

  摘要：

  一系列式[RuCl 2（L）（CO）2 ]的钌（II）二羰基配合物（L = bpy CH3，CH3 = 4,4'-二甲基-2,2'-联吡啶，bpy CH3，CHO = 4 '-甲基-2,2'-联吡啶-4-羧醛，bpy CH3，COOH = 4'-甲基-2,2'-联吡啶-4-羧酸，CppH = 2-（吡啶-2-基）嘧啶- 4-羧酸，dppzcH =二吡啶基[3,2-a：2'，3'-c]吩嗪-11-羧酸）和[RuCl（L）（CO）2 ] +（L = tpy COOH合成了6-（2,2'：6'，2''-叔吡啶-4'-酰氧基）己酸）。此外，还开发了高产率的含有2-（吡啶-2-基）嘧啶配体的肽核酸（PNA）单体的合成方法，并将该化合物用于制备第一个Ru（II）二羰基配合物，将[RuCl 2（CPP-L-PNA）（CO）2 ]，（CPP-L-PNA =叔丁基- ñ - [2-（ñ -9-芴）氨基乙基]

  DOI：

  10.1021/ic400746n

文献信息

• Ruthenium(II) Complexes Incorporating 2-(2′-Pyridyl)pyrimidine-4-carboxylic Acid
  作者：Nickita Nickita、Gilles Gasser、Pauline Pearson、Matthew J. Belousoff、Lai Y. Goh、Alan M. Bond、Glen B. Deacon、Leone Spiccia

  DOI：10.1021/ic800972x

  日期：2009.1.5

  precursor is the same as in the final product. The related complex [RuII(phen)2(cppH)](PF6)2·2H2O (2) (phen = 1,10-phenanthroline) was similarly synthesized. [RuII(bpy)(dppz)(cppH)](PF6)2·CH3CN (3) (dppz = dipyrido[3,2,-a;2′,3-c]phenazine) was also prepared by photochemical decarbonylation of [RuII(bpy)(CO)2Cl2] giving [RuII(bpy)(CO)Cl2]2 followed by bridge splitting with dppz to generate [RuII(bp

  制备了具有单一羧酸盐官能度的新的双齿配体2-（2'-吡啶基）嘧啶-4-羧酸（cppH），并将其用于一系列钌（II）配合物的合成。这种新的配体与Ru II（bpy）2 Cl 2的反应导致原料发生意外的氧化，从而生成[Ru III（bpy）2 Cl 2 ] Cl·H 2 O和低产率的[Ru II（bpy） ）2（cppH）]（PF 6）2 ·H 2 O（1）加水KPF 6溶液（bpy = 2,2'-联吡啶，cpp = 4-羧酸盐-2'-吡啶基-2-嘧啶）。通过缓慢蒸发1的水溶液获得的1a晶体[Ru II（bpy）2（cpp）]（PF 6）的X射线晶体结构测定表明，氮在cpp中的羧酸酯基对位−配体配位至钌（II）中心，而不是该基团的邻位。相同的复合物通过的的[Ru脱羰制备II（cppH）（CO）2氯2 ]·H 2 ○在联吡啶的存在下与过量的三甲胺N-氧化物的（ME 3NO），作为脱羰剂。前体中c
• Ru(<scp>ii</scp>)-Peptide bioconjugates with the cppH linker (cppH = 2-(2′-pyridyl)pyrimidine-4-carboxylic acid): synthesis, structural characterization, and different stereochemical features between organic and aqueous solvents
  作者：Federica Battistin、Daniel Siegmund、Gabriele Balducci、Enzo Alessio、Nils Metzler-Nolte

  DOI：10.1039/c8dt03575j

  日期：——

  isomers), depending on whether the nitrogen atom ortho (No) or para (Np) to the carboxylate on C4 in the pyrimidine ring binds the metal ion. Thus, one of the aims of this work was to obtain pairs of stereoisomeric conjugates and investigate their biological (anticancer, antibacterial) activity. A thorough NMR characterization clearly indicated that in all cases exclusively Np conjugates were obtained

  三个新的Ru（II）生物缀合物与神经降压素的C末端的六肽序列，RRPYIL，即反式，顺式-RuCl 2（CO）2（cppH-RRPYIL-κ Ñ p）（7），的[Ru（[9] ANES 3）（cppH-RRPYIL-κ ñ p）（PTA）]（Cl）的2（8），和的[Ru（[9] ANES 3）Cl（上cppH-RRPYIL-κ ñ p）]氯（11），其中cppH是不对称的连接基2-（2'-吡啶基）嘧啶-4-羧酸，以纯净形式制备，并在溶液中进行结构表征。cppH接头能够形成立体异构体（即键异构体），具体取决于嘧啶环C4上羧酸根的氮原子是邻位（N o）还是对位（N p）与金属离子结合。因此，这项工作的目的之一是获得一对立体异构共轭物，并研究其生物学（抗癌，抗菌）活性。彻底的NMR表征清楚地表明，在所有情况下，仅以纯净形式获得N p共轭物。此外，NMR研究表明，虽然在DMSO- d 6中每个缀合物都作为一个单一物种存在，但在D
• ¹⁵N NMR spectroscopy unambiguously establishes the coordination mode of the diimine linker 2-(2′-pyridyl)pyrimidine-4-carboxylic acid (cppH) in Ru(<scp>ii</scp>) complexes
  作者：Federica Battistin、Gabriele Balducci、Nicola Demitri、Elisabetta Iengo、Barbara Milani、Enzo Alessio

  DOI：10.1039/c5dt02361k

  日期：——

  We investigated the reactivity of three Ru(II) precursors – trans,cis,cis-[RuCl2(CO)2(dmso-O)2], cis,fac-[RuCl2(dmso-O)(dmso-S)3], and trans-[RuCl2(dmso-S)4] – towards the diimine linker 2-(2′-pyridyl)pyrimidine-4-carboxylic acid (cppH) or its parent compound 4-methyl-2-(2′-pyridyl)pyrimidine ligand (mpp), in which a methyl group replaces the carboxylic group on the pyrimidine ring. In principle, both

  我们研究了三种Ru（II）前体的反应性-反式，顺式，顺式[RuCl 2（CO）2（dmso- O）2 ]，顺式，fac- [RuCl 2（dmso- O）（dmso- S）3 ]和反式-[RuCl 2（dmso- S）4] –朝向二亚胺连接基2-（2'-吡啶基）嘧啶-4-羧酸（cppH）或其母体化合物4-甲基-2-（2'-吡啶基）嘧啶配体（mpp），其中甲基取代嘧啶环上的羧基。原则上，取决于嘧啶环如何通过氮原子邻位（N o）或对位（N p）到位置4的小组。这项工作的主要目的是建立光谱指纹，以在没有X射线结构表征的情况下区分cppH / mpp的配位模式。借助此处描述的新配合物以及我们先前报告的其他配合物，我们成功地在自然数量的15 N同位素上记录了 1 H，15 N} -HMBC NMR光谱，该光谱具有一定数量的完全表征的Ru（II）–cppH / mpp化合物，其中大多数是立体异构体和/或键合异构体。因此，我们发现15
• Electrochemiluminescent Monomers for Solid Support Syntheses of Ru(II)-PNA Bioconjugates: Multimodal Biosensing Tools with Enhanced Duplex Stability
  作者：Tanmaya Joshi、Gregory J. Barbante、Paul S. Francis、Conor F. Hogan、Alan M. Bond、Gilles Gasser、Leone Spiccia

  DOI：10.1021/ic202761w

  日期：2012.3.5

  The feasibility of devising a solid support mediated approach to multimodal Ru(II)-peptide nucleic acid (PNA) oligomers is explored. Three Ru(II)-PNA-like monomers, [Ru(bpy)(2)(Cpp-L-PNA-OH)](2+) (M1), [Ru(phen)(2)(Cpp-L-PNA-OH)](2+) (M2), and [Ru(dppz)(2)(Cpp-L-PNA-OH)](2+) (M3) (bpy = 2,2'-bipyridine, phen = 1,10-phenanthroline, dppz = dipyrido[3,2-a:2',3'-c]phenazine, Cpp-L-PNA-OH = [2-(N-9-fluorenylmethoxycarbonyl)aminoethyl]-N-[6-(2-(pyridin-2yl)pyrimidine-4-carboxamido)hexanoyl]-glycine), have been synthesized as building blocks for Ru(II)-PNA oligomers and characterized by IR and H-1 NMR spectroscopy, mass spectrometry, electrochemistry and elemental analysis. As a proof of principle, M1 was incorporated on the solid phase within the PNA sequences H-g-c-a-a-t-a-a-a-a-Lys-NH2 (PNA1) and H-P-K-K-K-R-K-V-g-c-a-a-t-a-a-a-a-lys-NH2 (PNA4) to give PNA2(H-g-c-a-a-t-a-a-a-a-M1-lys-NH2) and PNA3 (H-P-K-K-K-R-K-V-g-c-a-a-t-a-a-a-a-M1-lys-NH2), respectively. The two Ru(II) PNA oligomers, PNA2 and PNA3, displayed a metal to ligand charge transfer (MLCT) transition band centered around 445 nm and an emission maximum at about 680 nm following 450 nm excitation in aqueous solutions (10 mM PBS, pH 7.4). The absorption and emission response, of the duplexes formed with the cDNA strand (DNA: 5'-T-T-T-T-T-T-T-A-T-T-G-C-T-T-T-3') showed no major Variations, suggesting that the electronic properties of the Ru(II) complexes are largely unaffected by hybridization. The thermal stability of the PNA center dot DNA duplexes, as evaluated from UV melting experiments, is enhanced compared to the corresponding nonmetalated duplexes. The melting temperature (T-m) was almost 8 degrees C higher for PNA2 center dot DNA duplex, and 4 degrees C for PNA3 center dot DNA duplex, with the stabilization attributed to the electrostatic interaction between the cationic residues (Ru(II) unit and positively charged lysine/arginine) and the polyanionic DNA backbone. In presence of tripropylamine (TPA) as co-reactant, PNA2, PNA3, PNA2 center dot DNA and PNA3 center dot DNA displayed strong electrochemiluminescence (ECL) signals even at submicromolar concentrations. Importantly, the combination of spectrochemical, thermal and ECL properties possessed by the Ru(II)-PNA sequences offer an elegant approach for the design of highly sensitive multimodal biosensing tools.