4-(pyridazin-4-yl)butanoic acid | 1251542-14-9

• 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: 4-(pyridazin-4-yl)butanoic acid
• 英文别名: 4-pyridazinylbutanoic acid；pyridazine-4-butanoic acid；4-Pyridazin-4-ylbutanoic acid；4-pyridazin-4-ylbutanoic acid
• CAS: 1251542-14-9
• 化学式: C₈H₁₀N₂O₂
• 分子量: 166.18
• InChiKey: DFJHFKKYCMKVKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  63.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  五羰基氯铼(I) 、 4-(pyridazin-4-yl)butanoic acid 以 甲苯 为溶剂， 以90%的产率得到(ReCl(CO)3)2((4-pyridazin-4-yl)butanoic acid)
  参考文献：
  名称：

  Luminescent conjugates between dinuclear rhenium(i) complexes and peptide nucleic acids (PNA) for cell imaging and DNA targeting

  摘要：

  通过一种可靠的固相合成方法，成功合成了新型发光二核铼(I)三羰基复合物-PNA缀合物。对其光物理性质进行了测量。最具发光性的Re-PNA缀合物7显示出有趣的双光子吸收(TPA)特性，这些特性被用于成像实验，以证明其容易被活细胞摄取。

  DOI：

  10.1039/c0cc00450b
• 作为产物：
  描述：

  1,2,4,5-四嗪 、 5-己炔酸 以 1,4-二氧六环 为溶剂， 以68%的产率得到4-(pyridazin-4-yl)butanoic acid
  参考文献：
  名称：

  双核rh配合物和17α-乙炔基雌二醇之间的发光共轭物：合成，光物理特征和细胞成像

  摘要：

  描述了双核rh配合物和雌二醇之间的三种新的发光共轭物，即E2-Re。衍生物具有通式[Re 2（μ-Cl）2（CO）6（μ-R-pydz-17α-乙炔基雌二醇）]（R-pydz =功能化的1,2-哒嗪），其中雌二醇部分共价结合到哒嗪配体的β位上。研究了不同的合成途径，包括贫电子的1,2,4,5-四嗪与17α-乙炔基雌二醇之间的反型[4 + 2] Diels Alder环加成反应，以合成E2-Re1。三个E2-Re结合物在硅胶上纯化，以光谱纯净的形式分离，产率中等至良好（28–50％）。从光谱学和光物理的角度对所有E2-Re共轭物进行了全面表征。还报道了在人MCF-7和231细胞上进行的细胞内化实验，显示出有趣的染色差异，具体取决于将雌二醇单元连接至有机金属片段的间隔子的性质。此外，首次报道了这些缀合物还适合于染色简单的多细胞生物，即，处于不同发育阶段的肠小孢子（Ciona intestinalis）胚胎和幼虫。

  DOI：

  10.1039/c8ob02472c

文献信息

• Luminescent conjugates between dinuclear rhenium(i) complexes and peptide nucleic acids (PNA) for cell imaging and DNA targeting
  作者：Elena Ferri、Daniela Donghi、Monica Panigati、Giuseppe Prencipe、Laura D'Alfonso、Ivan Zanoni、Clara Baldoli、Stefano Maiorana、Giuseppe D'Alfonso、Emanuela Licandro

  DOI：10.1039/c0cc00450b

  日期：——

  New luminescent dinuclear rhenium(I) tricarbonyl complex–PNA conjugates have been synthesized through a reliable solid-phase synthetic methodology. Their photophysical properties have been measured. The most luminescent Re–PNA conjugate 7 showed interesting two-photon absorption (TPA) properties, that were exploited for imaging experiments, to demonstrate its easy uptake into living cells.

  通过一种可靠的固相合成方法，成功合成了新型发光二核铼(I)三羰基复合物-PNA缀合物。对其光物理性质进行了测量。最具发光性的Re-PNA缀合物7显示出有趣的双光子吸收(TPA)特性，这些特性被用于成像实验，以证明其容易被活细胞摄取。
• Luminescent dinuclear rhenium(I) PNA conjugates for microRNA-21 targeting: Synthesis, chemico-physical and biological characterization
  作者：Silvia Cauteruccio、Monica Panigati、Lorenzo Veronese、Nadia Zaffaroni、Marco Folini、Emanuela Licandro

  DOI：10.1016/j.jorganchem.2019.02.020

  日期：2019.5

  photoluminescence behavior of the organometallic fragments: emission from 3MLCT excited states, centered in a range between 580 and 610 nm, was observed, with satisfactory photoluminescence quantum yields (Φ = ca. 0.03–0.01, in aerated water/acetonitrile solution 1/1). Experiments of cell uptake, performed with living prostate cancer cells showed that the length of the aliphatic linker between the rhenium complex

  具有通式[Re 2（μ-Cl）2（CO）6（μ-1,2-二嗪）]的两种不同的发光complex络合物，其中包含两种不同的二嗪配体，即4-（哒嗪-4-基）制备了-丁酸（Re-1）和8-（5-甲基哒嗪-4-基）-辛酸（Re-2）。利用羧酸部分的存在，两个复合物进一步共价连接到一个20聚体的寡聚体（PNA1），其核碱基序列与成熟的miR-21-5p（5'-TCAACATCAGTCTGATAAGCTA-3'）互补以及20聚体低聚物（PNA2）用作带有序列5'-GTGTAACACGTCCTATACGCC-3'的阴性对照。对所得的四种Re-PNA偶联物进行表征，并用于靶向DU145前列腺癌细胞系中的miR-21。与PNA的结合不会干扰有机金属片段的光致发光行为：观察到3个MLCT激发态的发射中心在580至610 nm之间，具有令人满意的光致发光量子产率（Φ=约0.03-0.01，在加气水/乙腈溶液1/
• Triarylamine-based hydrido-carboxylate rhenium(<scp>i</scp>) complexes as photosensitizers for dye-sensitized solar cells
  作者：Lorenzo Veronese、Elsa Quartapelle Procopio、Thomas Moehl、Monica Panigati、Kazuteru Nonomura、Anders Hagfeldt

  DOI：10.1039/c9cp00856j

  日期：——

  light harvesting. Cyclic voltammetry experiments, performed on derivatives containing the methyl ester of the pyridazine ligands, show narrow electrochemical band gaps in the range of 1.36–1.84 eV. Solar cells with each dye have been prepared, using both iodide/triiodide and cobalt redox couples as the electrolytes, platinum or carbon as the counter electrodes, and TiO2 or SnO2 as the metal oxide photoelectrodes

  基于双核a络合物和（E）-3-（5-（4-（双（2'，4'-二丁氧基-[1,1'-联苯] -4-基）氨基）苯基）的两种新型染料已经研究了噻吩-2-基）-2-氰基丙烯酸（即D35）作为染料敏化太阳能电池（DSSC）的敏化剂。已使用两种不同的哒嗪配体，即染料2的4-哒嗪-羧酸（[Re 2（μ-H）（-D35）（CO）6（μ-哒嗪-4-COOH）]）和4-哒嗪基-染料3的丁酸（[Re 2（μ-H）（-D35）（CO）6（μ-哒嗪-4-C 3 H 6-COOH）]。已将这些新染料的性能与含有裸露的4-二苯基氨基苯甲酸（即TPA）作为辅助配体（染料1）的染料的性能进行了比较。与染料1相比，染料2和3在TiO 2上的487–493 nm范围内的吸收强度显着提高了十倍胶片，大大改善了采光效果。在含有哒嗪配体甲酯的衍生物上进行的循环伏安法实验显示，电化学带隙在1.36–1.84 eV范围内。已经制备了具有
• Luminescent Conjugates between Dinuclear Rhenium Complexes and Peptide Nucleic Acids (PNA): Synthesis, Photophysical Characterization, and Cell Uptake
  作者：Cristina Mari、Monica Panigati、Laura D’Alfonso、Ivan Zanoni、Daniela Donghi、Laura Sironi、Maddalena Collini、Stefano Maiorana、Clara Baldoli、Giuseppe D’Alfonso、Emanuela Licandro

  DOI：10.1021/om3004515

  日期：2012.8.27

  Different PNA decamers have been appended to a luminescent [Re-2(mu-Cl)(2)(CO)(6)(mu-1,2-diazine)] complex, to obtain conjugates suitable for cellular imaging. The new compounds can be dissolved in water in the presence of an amount of DMSO as small as 0.4-0.6 mol %. The conjugation with PNA did not perturb the photoluminescence behavior of the organometallic fragment: emission from (MLCT)-M-3 excited states, centered at ca. 610 nm, was observed, with satisfactory photoluminescence quantum yields (Phi = ca. 0.01, in aerated water). Moreover, the emission could be stimulated also by two-photon excitation. Experiments of cell uptake, performed with different cell lines and under different experimental conditions, showed that the nature of the PNA oligomer strongly affects the biointeraction, while no major differences were observed among the cell lines investigated. The Re-PNA conjugates containing neutral PNA decamers (either homothymine or a standard sequence of the four nucleobases) showed a marked tendency to concentrate in the nuclear region, whereas nucleus penetration was more difficult for the free dirhenium complex. Staining of nucleus and cytoplasm with different colors was generally observed. No nucleus penetration was instead observed for a water-soluble Re-PNA homothymine decamer end-capped with four lysine residues, which localized in endosome-like compartments.
• Luminescent conjugates between dinuclear rhenium complexes and 17α-ethynylestradiol: synthesis, photophysical characterization, and cell imaging
  作者：Matteo Proverbio、Elsa Quartapelle Procopio、Monica Panigati、Silvia Mercurio、Roberta Pennati、Miriam Ascagni、Roberta Leone、Caterina La Porta、Michela Sugni

  DOI：10.1039/c8ob02472c

  日期：——

  between the electron poor 1,2,4,5-tetrazine and 17α-ethynylestradiol for the synthesis of E2-Re1. The three E2-Re conjugates are purified on silica gel and isolated in a spectroscopically pure form in moderate to good yields (28–50%). All the E2-Re conjugates are comprehensively characterized from the spectroscopic and photophysical points of view. Cellular internalization experiments on human MCF-7 and

  描述了双核rh配合物和雌二醇之间的三种新的发光共轭物，即E2-Re。衍生物具有通式[Re 2（μ-Cl）2（CO）6（μ-R-pydz-17α-乙炔基雌二醇）]（R-pydz =功能化的1,2-哒嗪），其中雌二醇部分共价结合到哒嗪配体的β位上。研究了不同的合成途径，包括贫电子的1,2,4,5-四嗪与17α-乙炔基雌二醇之间的反型[4 + 2] Diels Alder环加成反应，以合成E2-Re1。三个E2-Re结合物在硅胶上纯化，以光谱纯净的形式分离，产率中等至良好（28–50％）。从光谱学和光物理的角度对所有E2-Re共轭物进行了全面表征。还报道了在人MCF-7和231细胞上进行的细胞内化实验，显示出有趣的染色差异，具体取决于将雌二醇单元连接至有机金属片段的间隔子的性质。此外，首次报道了这些缀合物还适合于染色简单的多细胞生物，即，处于不同发育阶段的肠小孢子（Ciona intestinalis）胚胎和幼虫。