2-{(Z)-phenyl[2-(pyridin-2-yl)hydrazinylidene]methyl}pyridine | 95526-04-8

• 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: 2-{(Z)-phenyl[2-(pyridin-2-yl)hydrazinylidene]methyl}pyridine
• 英文别名: (Z)-2-(phenyl(2-(pyridin-2-yl)hydrazono)methyl)pyridine；2-(Phenyl(2-(pyridin-2-yl)hydrazono)methyl)pyridine；N-[(Z)-[phenyl(pyridin-2-yl)methylidene]amino]pyridin-2-amine
• CAS: 95526-04-8
• 化学式: C₁₇H₁₄N₄
• 分子量: 274.325
• InChiKey: ZFZHDOZUCPKKKI-FXBPSFAMSA-N

物化性质

• 熔点：
  145-146 °C(Solv: ethanol (64-17-5))
• 沸点：
  459.2±43.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [Re(carbonyl)3(water)3]Br 、 2-{(Z)-phenyl[2-(pyridin-2-yl)hydrazinylidene]methyl}pyridine 以 甲醇 为溶剂， 反应 3.0h， 以70%的产率得到fac-Re(CO)₃(bpph)Br
  参考文献：
  名称：

  Synthesis of (Pyridin-2-YL)Hydrazone Rhenium(I) Tricarbonyl Complexes that Exhibit pH-Sensitive Fluorescence

  摘要：

  There is great potential for novel diagnostic and therapeutic agents that combine multiple imaging modalities. The combination of optical and radionuclide imaging systems is particularly promising for the improved management of cancer. We describe a new heteroorganometallacyclic system containing the (2-pyridyl)hydrazono-Re(CO)(3) that exhibits pH-sensitive photophysical properties. This optical reporter group was easily incorporated into a novel synthetic probe for targeting estrogen receptors in cancer. The efficient complexation conditions are expected to be compatible with Tc-99m-radiolabeling to obtain dual function imaging probes.

  DOI：

  10.1007/s10593-014-1469-4
• 作为产物：
  描述：

  2-肼吡啶 、 2-苯甲酰吡啶 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.5h， 以75%的产率得到2-{(Z)-phenyl[2-(pyridin-2-yl)hydrazinylidene]methyl}pyridine
  参考文献：
  名称：

  具有不同核数和几何形状的铜（II）配合物：合成，结构表征，抗氧化SOD活性和抗增殖性能

  摘要：

  摘要合成了具有（Z）-2-（苯基（2-（吡啶-2-基）肼基）甲基）吡啶（L）的新型铜（II）配合物，并采用多种物理化学方法对其进行了表征。配合物的几何形状可分为单核和双核。配合物1 [Cu（L）（Cl）2]是单核，而配合物2的固态结构包含单核和双核配合物2a [Cu（L）（H2O） （SO4）]和2b，[Cu2（L）2（μ-SO4）2]。2的晶胞包含两个单元的单核复合物2a和一个单元的双核复合物2b。所有单核和双核络合物中所含的铜原子均呈扭曲的方形棱锥几何形状。本研究表明，可以通过改变合成条件和方法来实现具有不同核数和几何形状的配合物。配合物的可变温度磁化率测量结果表明存在弱的反铁磁相互作用。这些相互作用是由1中的分子间氢键和2中的对称硫酸盐桥介导的。由于两个铜（II）离子之间的自旋相互作用，在1和2的多晶状态下的EPR光谱在〜2.149处显示了宽信号。 。DMSO中配合物1和2的循环伏安

  DOI：

  10.1016/j.poly.2020.114624

文献信息

• Novel hydrazone-based and oxime-based fluorescent and chromophoric/pro-fluorescent and pro-chromophoric reagents and linkers
  申请人：Schwartz David A.

  公开号：US20080221343A1

  公开（公告）日：2008-09-11

  Conjugationally extended hydrazine compositions of the formula (RR 2 )N(H) n (NH 2 ) n , fluorescent hydrazone compositions of the formula (RR 2 )NN═C(R 1 R 2 ), methods of the formation of hydrazones from the reaction of conjugationally extended hydrazines with conjugationally extended carbonyls and methods of their use in assays systems are described. Use of these conjugationally extended hydrazine and oxime compositions for direct calorimetric and fluorometric assays wherein a chromophore or the fluorophore is incorporated into the linker that is positioned between a reactive linking moiety and a biotin molecule. More specifically the linker comprises one molecule of a high affinity binding pair such as for example biotin of the biotin/avidin high affinity binding pair, connected to a spacer molecule such as for example a length of polyethyleneglycol followed by a pro-chromophoric, chromophoric, pro-fluorescent or fluorescent moiety connected to an amino-, thiol- or carbohydrate-reactive moiety such as for example succinimidyl, maleimido or aminoxy group respectively, that may covalently link to a biomolecule.

  描述了公式(RR2)N(H)n(NH2)n的共轭扩展肼组合物，公式(RR2)NN═C(R1R2)的荧光肼酮组合物，以及从共轭扩展肼与共轭扩展羰基化合物反应形成肼酮的方法，以及在测定系统中使用它们的方法。利用这些共轭扩展肼和肟组合物进行直接量热和荧光测定，其中色团或荧光团被并入连接基团中，该连接基团位于反应性连接基团和生物素分子之间。更具体地，连接基团包括一分子高亲和性结合对之一，例如生物素/亲和素高亲和性结合对之一，连接到一个间隔分子，例如一段聚乙二醇长度，后接一个前色团、色团、前荧光团或荧光团，连接到一个氨基、硫醇或碳水化合物反应性基团，例如琥珀酰亚胺基、马来酰亚胺基或氨氧基团，可以共价连接到生物分子。
• Butler, Richard N.; Johnston, Sean M., Journal of the Chemical Society. Perkin transactions I, 1984, p. 2109 - 2116
  作者：Butler, Richard N.、Johnston, Sean M.

  DOI：——

  日期：——
• Azinyl and Diazinyl Hydrazones Derived from Aryl <i>N</i>-Heteroaryl Ketones:  Synthesis and Antiproliferative Activity^,
  作者：Johnny Easmon、Gottfried Heinisch、Gerhard Pürstinger、Thierry Langer、Jürgen K. Österreicher、Hans H. Grunicke、Johann Hofmann

  DOI：10.1021/jm970255w

  日期：1997.12.1

  A series of N-heteroaryl hydrazones derived from aryl N-heteroaryl or bis-N-heteroaryl methanones was prepared in search for potential novel antitumor agents. The stereochemistry of these compounds was established by means of NMR spectroscopy. Antiproliferative activity was determined in a panel of human tumor cell Lines (CCRF-CEM, Burkitt's lymphoma, HeLa, ZR-75-1, HT-29, and MEXF 276L) in vitro. Generally, the new compounds were found to be more patent (IC(50) = 0.011-0.436 mu M) than the ribonucleotide reductase inhibitor hydroxyurea (IC(50) = 140 mu M) Most of the compounds exhibited the highest activity against Burkitt's lymphoma with an IC(50) Of 0.011-0.035 mu M. [(14)C]Cytidine incorporation into DNA was quantitated for selected hydrazones (Z-A, E-1, Z-3, Z-4, E-5, Z-5, E-13, E-18, Z-19, Z-24, and E-26) as a measure of the inhibition of-ribonucleotide reductase in Burkitt's lymphoma cells. The E-configurated compounds were found to inhibit [(14)C]cytidine incorporation to a greater extent (IC(50) = 0.67-5.05 mu M) than the Z-isomers (IC(50) = 7.20 to > 10 mu M). Principal component analysis of the IC(50) values obtained for inhibition of cell proliferation revealed that the cell lines tested can be grouped into three main families showing different sensitivities toward the compounds in our series [(i) CCRF-CEM, Burkitt's lymphoma, and Hela; (ii) HT-29; and (iii) MEXF 276 L].
• Synthesis and characterization of penta-coordinated copper(II) complexes with hydrazido based ligand and imidazole as auxiliary ligand
  作者：Abhay K. Patel、Rajendra N. Jadeja、Ray J. Butcher

  DOI：10.1016/j.jics.2021.100182

  日期：2021.11
• PELLERANO, C.;SAVINI, L.;MASSARELLI, P., FARMACO. ED. SCI., 1985, 40, N 9, 645-654
  作者：PELLERANO, C.、SAVINI, L.、MASSARELLI, P.

  DOI：——

  日期：——