1,4-bis(2-quinolyl)-2,3-diaza-1,3-butadiene | 27346-97-0

• 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: 1,4-bis(2-quinolyl)-2,3-diaza-1,3-butadiene
• 英文别名: 1-quinolin-2-yl-N-(quinolin-2-ylmethylideneamino)methanimine
• CAS: 27346-97-0
• 化学式: C₂₀H₁₄N₄
• 分子量: 310.358
• InChiKey: DAYMATJJOGQAIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  六氟磷酸钾 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 1,4-bis(2-quinolyl)-2,3-diaza-1,3-butadiene 以 甲醇 、 二氯甲烷 为溶剂， 以71 %的产率得到
  参考文献：
  名称：

  双喹啉钌 (II) 芳烃复合物对去势抵抗性前列腺癌细胞具有亚微摩尔细胞毒性

  摘要：

  使用2-双(喹啉-2-基亚甲基)肼(L)开发了一种新型Ru( II )芳烃氯化有机金属络合物[(η 6 - p -伞花烃)(L)RuCl]PF 6 (命名为pCYRuL )，其表现出对去势抵抗性前列腺癌 (CRPC) 具有有效的抗癌活性 (IC 50 = 0.71 μM)，在去势抵抗性人前列腺癌细胞系中，其疗效比标准药物顺铂 (IC 50 = 31.3 μM) 强 45 倍。 PC-3），但对正常人肾细胞（HK2）和正常乳腺细胞（MCF10A）无毒，并发现pCYRuL通过诱导细胞凋亡和 PC-3 细胞 G2/M 期的细胞周期阻滞发挥抗癌活性。

  DOI：

  10.1039/d3cc05083a
• 作为产物：
  描述：

  喹啉-2-甲醛 在 一水合肼 作用下， 以 乙醇 为溶剂， 以85%的产率得到1,4-bis(2-quinolyl)-2,3-diaza-1,3-butadiene
  参考文献：
  名称：

  Azine-Based Receptor for Recognition of Hg²⁺ Ion: Crystallographic Evidence and Imaging Application in Live Cells

  摘要：

  A newly synthesized azine-based receptor (L) is found to show remarkable specificity toward the Hg2+ ion in aqueous media over other metal ions. Coordination of L to Hg2+ induces a detectable change in color and a turn-on fluorescence response. Restricted C=N isomerization of the azine moieties in the excited state as well as the Photoinduced Electron Transfer (PET) involving the lone pair of electrons of N-1/N-2 on coordination of L to the Hg2+ ion account for the turn-on fluorescence response. This reagent could be used for imaging the accumulation of Hg2+ ions in Epithelial cell line KB 31 cells.

  DOI：

  10.1021/ol102204r

文献信息

• Azine-Based Receptor for Recognition of Hg²⁺ Ion: Crystallographic Evidence and Imaging Application in Live Cells
  作者：Moorthy Suresh、Amal Kumar Mandal、Sukdeb Saha、E. Suresh、Amit Mandoli、Rosa Di Liddo、Pier Paolo Parnigotto、Amitava Das

  DOI：10.1021/ol102204r

  日期：2010.12.3

  A newly synthesized azine-based receptor (L) is found to show remarkable specificity toward the Hg2+ ion in aqueous media over other metal ions. Coordination of L to Hg2+ induces a detectable change in color and a turn-on fluorescence response. Restricted C=N isomerization of the azine moieties in the excited state as well as the Photoinduced Electron Transfer (PET) involving the lone pair of electrons of N-1/N-2 on coordination of L to the Hg2+ ion account for the turn-on fluorescence response. This reagent could be used for imaging the accumulation of Hg2+ ions in Epithelial cell line KB 31 cells.
• Cu(II)-selective fluorescence of a bis-quinolylimine derivative
  作者：Chizuru Ichimura、Yasuhiro Shiraishi、Takayuki Hirai

  DOI：10.1016/j.jphotochem.2010.10.018

  日期：2011.1

  A new bis-quinolylimine ligand containing an azadiene moiety, 1,4-bis(2-quinolyI)-2,3-diaza-1,3-buthadiene (1), was synthesized by one-step facile condensation. This simple ligand, when dissolved in acetonitrile, shows a Cu(2+)-selective fluorescence enhancement. Coordination of 1 with Cu(2+) produces two kinds of complexes with 1:1 and 1:2 stoichiometries. The 1:2 complex shows a strong fluorescence (Phi(F) = 0.37), while the 1:1 complex does not (Phi(F) < 0.01). Ab initio molecular orbital calculation reveals that the 1:1 complex has a distorted structure, while the 1:2 complex has a planar structure. The planar configuration of the 1:2 complex, therefore, allows an extended pi-conjugation over the entire molecule and, hence, results in fluorescence enhancement. (C) 2010 Elsevier B.V. All rights reserved.
• A bis-quinoline ruthenium(<scp>ii</scp>) arene complex with submicromolar cytotoxicity in castration-resistant prostate cancer cells
  作者：Tanveer A. Khan、Kishalay Bhar、Rohit Samanta、Surabhi Bhatt、Mamta Singh、Reshma Rani、Vinit Kumar、Anuj K. Sharma

  DOI：10.1039/d3cc05083a

  日期：——

  A new Ru(II) arene chlorido organometallic complex [(η6-p-cymene)(L)RuCl]PF6 (named as pCYRuL) using 2-bis(quinolin-2-ylmethylene) hydrazine (L) was developed that exhibits potent anticancer activity against castration-resistant prostate cancer (CRPC) (IC50 = 0.71 μM), and it is 45 times more effective than the standard drug cisplatin (IC50 = 31.3 μM) in a castration-resistant human prostatic adenocarcinoma

  使用2-双(喹啉-2-基亚甲基)肼(L)开发了一种新型Ru( II )芳烃氯化有机金属络合物[(η 6 - p -伞花烃)(L)RuCl]PF 6 (命名为pCYRuL )，其表现出对去势抵抗性前列腺癌 (CRPC) 具有有效的抗癌活性 (IC 50 = 0.71 μM)，在去势抵抗性人前列腺癌细胞系中，其疗效比标准药物顺铂 (IC 50 = 31.3 μM) 强 45 倍。 PC-3），但对正常人肾细胞（HK2）和正常乳腺细胞（MCF10A）无毒，并发现pCYRuL通过诱导细胞凋亡和 PC-3 细胞 G2/M 期的细胞周期阻滞发挥抗癌活性。