N-(pyridin-2-yl)quinolin-2-amine | 187218-02-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(pyridin-2-yl)quinolin-2-amine
• 英文别名: 2-Pyridyl-2-quinolylamine；N-pyridin-2-ylquinolin-2-amine
• CAS: 187218-02-6
• 化学式: C₁₄H₁₁N₃
• 分子量: 221.261
• InChiKey: LKKVSUQIZFOEEK-UHFFFAOYSA-N

物化性质

• 熔点：
  171.6-173.8 °C
• 沸点：
  392.2±22.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(pyridin-2-yl)quinolin-2-amine 、 7-溴庚酸乙酯 在 sodium hydride 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以55%的产率得到7-(pyridin-2-yl-quinolin-2-yl-amino)-heptanoic acid ethyl ester
  参考文献：
  名称：

  [EN] SCRIPTAID ISOSTERES AND THEIR USE IN THERAPY
  [FR] ISOSTÈRES DU SCRIPTAID ET LEUR UTILISATION EN THÉRAPIE

  摘要：

  本发明的化合物具有公式(I)：其中：…表示双键，X为C；或…表示单键，X为N、CH或CQR1；并且：n为1至10；R为H或QR1；每个R'独立地选自H和QR1；每个Q独立地选自键、CO、NH、S、SO、SO2或O；每个R1独立地选自C1-C10烷基、C2-C10烯基、C2-C10炔基、取代或不取代的芳基或杂芳基、酰基、C1-C10环烷基、卤素、C1-C10烷基芳基或C1-C10杂环烷基；L是含有氮的杂芳基；W是锌螯合残基；或其药用可接受盐。这些化合物在治疗中有用。

  公开号：

  WO2010086646A1
• 作为产物：
  描述：

  喹啉-N-氧化物 在 盐酸 、 sodium hydroxide 、 磺酰氯 作用下， 以 氯仿 为溶剂， 反应 20.0h， 生成 N-(pyridin-2-yl)quinolin-2-amine
  参考文献：
  名称：

  摘要：

  In reaction of quinoline N-oxide with 2-aminopyridine in the presence of tosyl chloride the substrate undergoes reductive amination into 2-pyridyl(2-quinolyl)an-line, and with 3- and 4-aminopyridines reductive tosylamination occurs to furnish N-tosyl derivatives of the corresponding 3- and 4-pyridyl(2-quinolyl)amines. N-tosyl derivatives of aminopyridines also react along reductive tosylamination pathway.

  DOI：

  10.1023/a:1020913929185

文献信息

• Hybrid organic‐inorganic Cu(II) iminoisonicotine@TiO ₂ @Fe ₃ O ₄ heterostructure as efficient catalyst for cross‐couplings
  作者：Mohamed Shaker S. Adam、Farman Ullah、Mohamed M. Makhlouf

  DOI：10.1111/jace.17098

  日期：2020.8

  immobilized copper catalyst (CuL@TiO2@Fe3O4) shell‐shell‐core system. The structural analysis revealed that the catalyst system is composed of both agglomerated nanospheres and deformed nanorods. Both copper catalysts, immobilized CuL@TiO2@Fe3O4 and un‐immobilized CuL were studied in heterogeneous and homogeneous catalysis, respectively, for Suzuki‐Miyaura (C–C) and Buchwald‐Hartwig (C–N) cross‐coupling reactions

  通过与Cu（II）离子配位，（CuL @ TiO 2 @Fe 3 O 4）和不将（CuL）固定在TiO 2上，由Cu（II）离子配位，由新的三齿亚氨基异烟碱配体（HL）合成了两种新型单核铜（II）络合物催化剂。Fe 3 O 4包覆的纳米颗粒。配体背面的酯部分用于固定在Fe 3 O 4纳米颗粒上。配体和CuL络合物均通过使用其他光谱技术（核磁共振，红外，紫外可见光谱和质谱以及元素分析）进行了全面表征。使用不同的分析技术来确定固定化铜催化剂（CuL @ TiO 2 @Fe 3 O 4）壳-壳-核系统的结构特征和形态。结构分析表明，该催化剂体系由团聚的纳米球和变形的纳米棒组成。两种铜催化剂，固定化的CuL @ TiO 2 @Fe 3 O 4分别在Suzuki-Miyaura（CC）和Buchwald-Hartwig（CN）的各种杂芳基卤化物的交叉偶联反应的非均相和均相催化中研究了CuL和未固定的
• Synthesis and biological evaluation of quinoline derivatives as potential anti-prostate cancer agents and Pim-1 kinase inhibitors
  作者：Kun Li、Ying Li、Di Zhou、Yinbo Fan、Hongye Guo、Tianyi Ma、Jiachen Wen、Dan Liu、Linxiang Zhao

  DOI：10.1016/j.bmc.2016.03.016

  日期：2016.4

  role in the anti-proliferative effects. Mechanistic studies revealed that 9g was a potential Pim-1 kinase inhibitor with abilities of cell cycle arrest and apoptosis induction. Considering of the increased activity of Pim-1 in prostate cancer, such compounds have potential to be developed as anti-prostate cancer agents.

  在这项工作中，设计并合成了一系列喹啉衍生物作为抗肿瘤剂。大多数喹啉类药物对人前列腺癌PC-3细胞系显示出有效的抗增殖活性。其中9d，9f和9g是最有效的化合物，其GI 50值分别为2.60、2.81和1.29μM。结构-活性关系分析表明，仲胺连接的喹啉和吡啶环在抗增殖作用中起重要作用。机理研究表明9g是潜在的Pim-1激酶抑制剂，具有细胞周期阻滞和凋亡诱导能力。考虑到Pim-1在前列腺癌中活性的提高，这类化合物具有开发成为抗前列腺癌药物的潜力。
• Cross Coupling of Substituted Anilines with Quinoline: Synthesis and Structural Characterization of HN(py)quin, PhN(py)quin, MesN(py)quin, and [PhN(py)(H-quin)]BF4
  作者：John J. Allen、Christopher E. Hamilton、Andrew R. Barron

  DOI：10.1007/s10870-009-9616-y

  日期：2010.2

  The molecular structure of RN(py)quin, with R=H (1), Ph (2), and Mes (3) and the protonated complex [PhN(py)(H-quin)]BF4 (4) have been determined. Compounds 2 and 3 both crystallize in a three bladed propeller conformation. Any π–π stacking observed is dominated by quinolyl···quinolyl stacks. In contrast to analogous derivatives the acidic proton in compound 4 is chelated by the pyridyl and quinolyl heterocycles in an asymmetric fashion. Crystal data: 1 group P21/c, a = 11.571(2), b = 6.116(1), c = 15.585(3) Å, β = 90.00(3)°, V = 1103.0(4) Å3, Z = 4, R = 0.0440, wR 2 = 0.1064. 2 group P21/n, a = 8.081(1), b = 13.920(3), c = 27.697(6) Å, β = 96.50(3)°, V = 3095(1) Å3, Z = 8, R = 0.0495, wR 2 = 0.1174. 3 group P21/c, a = 12.359(3), b = 12.585(3), c = 12.457(3) Å, β = 104.09(3)°, V = 1879.4(7) Å3, Z = 4, R = 0.0709, wR 2 = 0.1692. 4 group P21/c, a = 15.308(3), b = 7.585(1), c = 17.227(3) Å, β = 113.43(3)°, V = 1835.5(7) Å3, Z = 4, R = 0.0536, wR 2 = 0.1341. The molecular structure of RN(py)quin, with R=H, Ph, and Mes, and the protonated complex [PhN(py)(H-quin)]BF4 have been determined. The presence of π–π stacking observed is dominated by quinolyl···quinolyl rather than pyridyl···quinolyl or pyridyl···pyridyl interactions.

  已经确定了RN(py)quin的分子结构，其中R=H（1）、Ph（2）和Mes（3），以及质子化的复合物[PhN(py)(H-quin)]BF4（4）。化合物2和3均以三片桨叶旋转构型结晶。观察到的任何π–π堆叠主要由喹啉基···喹啉基堆叠主导。与类似衍生物相比，化合物4中的酸性质子是通过吡啶环和喹啉环以不对称的方式螯合。晶体数据：1组P21/c，a = 11.571(2)，b = 6.116(1)，c = 15.585(3) Å，β = 90.00(3)°，V = 1103.0(4) ų，Z = 4，R = 0.0440，wR² = 0.1064。2组P21/n，a = 8.081(1)，b = 13.920(3)，c = 27.697(6) Å，β = 96.50(3)°，V = 3095(1) ų，Z = 8，R = 0.0495，wR² = 0.1174。3组P21/c，a = 12.359(3)，b = 12.585(3)，c = 12.457(3) Å，β = 104.09(3)°，V = 1879.4(7) ų，Z = 4，R = 0.0709，wR² = 0.1692。4组P21/c，a = 15.308(3)，b = 7.585(1)，c = 17.227(3) Å，β = 113.43(3)°，V = 1835.5(7) ų，Z = 4，R = 0.0536，wR² = 0.1341。RN(py)quin的分子结构及质子化复合物[PhN(py)(H-quin)]BF4已经确定。观察到的π–π堆叠主要由喹啉基···喹啉基堆叠主导，而非吡啶基···喹啉基或吡啶基···吡啶基的相互作用。
• [EN] BICYCLIC COMPOUNDS USEFUL FOR TREATING DISEASES CAUSED BY RETROVIRUSES<br/>[FR] COMPOSÉS BICYCLIQUES UTILES POUR LE TRAITEMENT DE MALADIES CAUSÉES PAR DES RÉTROVIRUS
  申请人：SPLICOS

  公开号：WO2015001518A1

  公开（公告）日：2015-01-08

  Described herein are methods for preventing or treating a retroviral infection and/or for preventing, inhibiting or treating a disease caused by the retroviral infection. In certain aspects, the methods described herein include contacting a cell in need thereof with compound (I), wherein (II) means a pyridazine, a pyrimidine or a pyrazine group, R independently represent a hydrogen atom, a halogen atom or a group chosen among a –CN group, a hydroxyl group, a –COOR1 group, a (C1 -C3)fluoroalkyl group, a (C1 -C3)fluoroalkoxy group, a –NO2 group, a –NR1R2 group, a (C1-C4)alkoxy group, a phenoxy group and a (C1-C3)alkyl group, said alkyl being optionally mono-substituted by a hydroxyl group, n is 1, 2 or 3, n' is 1 or 2, R' is a hydrogen atom, a halogen atom or a group chosen among a (C1-C3)alkyl group,, a hydroxyl group, a –COOR1 group, a –NO2 group, a –NR1R2 group, a morpholinyl or a morpholino group, a N-methylpiperazinyl group, a (C1-C3)fluoroalkyl group, a (C1-C4)alkoxy group and a –CN group, Z is N or C, Y is N or C, X is N or C, W is N or C, T is N or C, U is N or C, to prevent or treat the retroviral infection and/or for preventing, inhibiting or treating a disease caused by the retroviral infection, wherein the retroviral infection is not HIV and the disease caused by the retroviral infection is not AIDS.

  本文描述了一种预防或治疗逆转录病毒感染和/或预防、抑制或治疗由逆转录病毒感染引起的疾病的方法。在某些方面，所述方法包括将化合物(I)与需要其治疗的细胞接触，其中(II)表示吡啶嗪、嘧啶或吡嗪基团，R独立地表示氢原子、卤素原子或在-CN基团、羟基基团、-COOR1基团、(C1-C3)氟代烷基团、(C1-C3)氟代烷氧基团、-NO2基团、-NR1R2基团、(C1-C4)烷氧基团、苯氧基团和(C1-C3)烷基团中选择的一种基团，所述烷基可以选择性地被羟基基团单取代，n为1、2或3，n'为1或2，R'为氢原子、卤素原子或在(C1-C3)烷基团、羟基基团、-COOR1基团、- 基团、-NR1R2基团、吗啉基或吗啉基团、N-甲基哌嗪基团、(C1-C3)氟代烷基团、(C1-C4)烷氧基团和-CN基团中选择的一种基团，Z为N或C，Y为N或C，X为N或C，W为N或C，T为N或C，U为N或C，以预防或治疗逆转录病毒感染和/或预防、抑制或治疗由逆转录病毒感染引起的疾病，其中逆转录病毒感染不是HIV，由逆转录病毒感染引起的疾病不是艾滋病。
• Organic element for electroluminescent devices
  申请人：Eastman Kodak Company

  公开号：US20030201415A1

  公开（公告）日：2003-10-30

  Disclosed is an OLED device comprising a light-emitting layer containing a host and a dopant where the dopant comprises a boron compound complexed by two ring nitrogens of a deprotonated bis(azinyl)amine ligand.

  本发明公开了一种OLED器件，包括一个发光层，该发光层包含主体和掺杂剂，其中掺杂剂包括被去质子的双(吖嗪基)胺配体的两个环状氮络合的硼化合物。