N-(2-pyridyl)-2-hydroxy-5-chlorobenzylamine | 362600-51-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-pyridyl)-2-hydroxy-5-chlorobenzylamine
• 英文别名: 4-chloro-2-(pyridin-2-ylaminomethyl)phenol；N-(2-pyridyl)-2-oxy-5-chlorobenzylaminate；N-(2-pyridyl)-2-oxy-5-chlorobenzylamine；4-Chloro-2-[(pyridin-2-ylamino)methyl]phenol
• CAS: 362600-51-9
• 化学式: C₁₂H₁₁ClN₂O
• 分子量: 234.685
• InChiKey: NAKIPYFXJZUDBK-UHFFFAOYSA-N

物化性质

• 沸点：
  404.3±35.0 °C(Predicted)
• 密度：
  1.354±0.06 g/cm3(Predicted)
• 溶解度：
  6.5 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  potassium tetrachloroplatinate(II) 、 N-(2-pyridyl)-2-hydroxy-5-chlorobenzylamine 以 甲醇 、 水 为溶剂， 反应 24.0h， 以81.4%的产率得到Pt[4-chloro-2-(pyridin-2-ylaminomethyl)phenol]Cl₂
  参考文献：
  名称：

  以还原的氨基吡啶席夫碱及其衍生物为配体的铂（II）配合物的合成表征和细胞毒性研究。

  摘要：

  制备了一系列还原氨基吡啶席夫碱铂（II）配合物作为潜在的抗癌药物，并通过NMR，IR光谱，元素分析和摩尔电导率进行了表征。UV和CD结果表明，这些化合物与鲑鱼精子DNA之间的结合方式可能是嵌入的。通过MTT测定法验证了这些复合物对A549，Hela和MCF-7细胞系的细胞毒性。某些复合物显示出比顺铂更好的针对Hela和MCF-7细胞系的细胞毒活性。

  DOI：

  10.1080/09168451.2016.1259550
• 作为产物：
  描述：

  对氯苯酚 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 21.0h， 生成 N-(2-pyridyl)-2-hydroxy-5-chlorobenzylamine
  参考文献：
  名称：

  以还原的氨基吡啶席夫碱及其衍生物为配体的铂（II）配合物的合成表征和细胞毒性研究。

  摘要：

  制备了一系列还原氨基吡啶席夫碱铂（II）配合物作为潜在的抗癌药物，并通过NMR，IR光谱，元素分析和摩尔电导率进行了表征。UV和CD结果表明，这些化合物与鲑鱼精子DNA之间的结合方式可能是嵌入的。通过MTT测定法验证了这些复合物对A549，Hela和MCF-7细胞系的细胞毒性。某些复合物显示出比顺铂更好的针对Hela和MCF-7细胞系的细胞毒活性。

  DOI：

  10.1080/09168451.2016.1259550

文献信息

• A new metal–metal bonded diruthenium(II,III) compound bridged by the dianionic tridentate ligand N-(2-pyridyl)-2-oxy-5-chlorobenzylaminate (5-Clsalpy2−)
  作者：Hitoshi Miyasaka、Chihiro Kachi-Terajima、Tomohiko Ishii、Masahiro Yamashita

  DOI：10.1039/b103186b

  日期：——

  The ligand-substitution reaction of Ru2(O2CCH3)4Cl with the tridentate ligand N-(2-pyridyl)-2-oxy-5-chlorobenzylaminate dianion (5-Clsalpy2−) led to the unique diruthenium(II,III) compound [Na(THF)2}Ru2(O2CCH3)2(5-Clsalpy)2}]·THF (1·THF) which revealed the characteristic 1-D chain structure of the repeating unit [–Na–O–Ru–Ru–O–]∞ and rich redox chemistry.

  Ru2(O2CCH3)4Cl与三叉配体 N-(2-吡啶基)-2-氧-5-氯苄基氨基二离子（5-Clsalpy2â）的配体置换反应产生了独特的二钌（II、III）化合物[Na(THF)2}Ru2(O2CCH3)2(5-Clsalpy)2}]Â-THF（1Â-THF），揭示了重复单元[âNaâOâRuâRuâOâ]â特有的一维链结构和丰富的氧化还原化学性质。
• A Family of Diruthenium Compounds with Dianionic Tridentate Ligands of <i>N</i>-(2-Pyridyl)-2-oxy-5-R-benzylaminate (R = H, Me, Cl, Br, NO₂):  Isolation, Structure Determination, and Electrochemistry
  作者：Hitoshi Miyasaka、Toru Izawa、Ken-ichi Sugiura、Masahiro Yamashita

  DOI：10.1021/ic034625k

  日期：2003.11.1

  The ligand substitution reaction of Ru-2(O2CCH3)(4)Cl with 5-substituted N-(2-pyridyl)-2-oxy-5-R-benzylaminate (R = H, Me, Cl, Br, NO2) resulted in a family of anionic diruthenium species of [Ru-2(O2CCH3)(2)(R-salpy)(2)](-) that were isolated by using Na+- or K+-18-crown-6-ether as the countercation: [A(18-crown-6)(S)(x)][Ru-2(O2CCH3)(2)(R-salpy)(2)] (A = Na+, K+; S = solvent; R = H, 1; Me, 2; Cl, 3; Br, 4; NO2, 5). All compounds were structurally characterized by X-ray crystallography. The structural features of the anionic parts are very similar among the compounds: two acetate and two R-salpy(2-) ligands are, respectively, located around the Ru-2 unit in a trans fashion, where the R-salpy2- ligand acts as a tridentate ligand having both bridging and chelating characters to form the M-M bridging/axial-chelating mode. Compounds 1 and 5 with K+-18-crown-6-ether have one-dimensional chain structures, the K+-18-crown-6-ether interacting with phenolate oxygens of the [Ru-2(O2CCH3)(2)(R-salpy)(2)](-) unit to form a repeating unit, [(KO)-K-...-O-...-Ru-Ru-O-...], whereas 2-4 are discrete. Cyclic voltammetry and differential pulse voltammetry revealed systematic redox activities based on the dimetal center and the substituted ligand, obeying the Hammett law with the reaction constants per substituent, rho, for the redox processes being 127 mV for Ru-2(5+)/Ru-2(4+), 185 mV for Ru-2(6+)/Ru-2(5+), 92 mV for Ru-2(7+)/Ru-2(6+), and 179 mV for R-salpy(-)/R-salpy(2-). For 3, the singly oxidized and reduced species, Ru-2(6+) and Ru-2(4+), respectively, generated by bulk controlled-potential electrolyses were finally monitored by spectroscopy. The singly oxidized species can also be slowly generated by air oxidation.
• A unique diruthenium(II, III) unit surrounded by tridentate ligands of N-(2-pyridyl)-2-oxy-5-chlorobenzylaminate
  作者：Hitoshi Miyasaka、Ken-ichi Sugiura、Masahiro Yamashita

  DOI：10.1016/s1387-7003(03)00185-0

  日期：2003.8

  A new metal-metal bonded diruthenium(II, III) compound with a dianionic tridentate ligand, N-(2-pyridyl)-2-oxy-5-chlorobenzylaminate (5-Clsalpy(2-)), was synthesized and structurally characterized as Li-2(THF)(4)Cl[Ru-2(5-Clsalpy)(3)] (1). The 5-Clsalpy(2-) ligand that acts as a bridging/chelating co-ligand afforded a unique coordination mode of [M-M bridging/equatorial-chelating] in addition to the "common" mode of [M-M bridging/axial-chelating] around the diruthenium unit of 1. (C) 2003 Elsevier Science B.V. All rights reserved.
• Synthesis characterization and cytotoxicity studies of platinum(II) complexes with reduced amino pyridine schiff base and its derivatives as ligands
  作者：Li-Jun Li、Qin-Qin Yan、Guo-Jun Liu、Zhen Yuan、Zhen-Hua Lv、Bin Fu、Yan-Jun Han、Jian-Long Du

  DOI：10.1080/09168451.2016.1259550

  日期：2017.6.3

  A series of reduced amino pyridine Schiff base platinum(II) complexes were prepared as potential anticancer drugs, and characterized by NMR, IR spectroscopy, elemental analysis, and molar conductivity. UV and CD results showed the binding mode between these compounds and salmon sperm DNA may be intercalation. The cytotoxicity of these complexes was validated against A549, Hela, and MCF-7 cell lines

  制备了一系列还原氨基吡啶席夫碱铂（II）配合物作为潜在的抗癌药物，并通过NMR，IR光谱，元素分析和摩尔电导率进行了表征。UV和CD结果表明，这些化合物与鲑鱼精子DNA之间的结合方式可能是嵌入的。通过MTT测定法验证了这些复合物对A549，Hela和MCF-7细胞系的细胞毒性。某些复合物显示出比顺铂更好的针对Hela和MCF-7细胞系的细胞毒活性。