N-((1H-imidazol-2-yl)methylene)aniline | 77302-63-7

• 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-((1H-imidazol-2-yl)methylene)aniline
• 英文别名: 1-(1H-imidazol-2-yl)-N-phenylmethanimine
• CAS: 77302-63-7
• 化学式: C₁₀H₉N₃
• 分子量: 171.202
• InChiKey: QWLQFZWMRSRJHH-UHFFFAOYSA-N

物化性质

• 沸点：
  368.3±25.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-((1H-imidazol-2-yl)methylene)aniline 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 N-(1H-咪唑-2-基甲基)苯胺
  参考文献：
  名称：

  Cardioselective Antiischemic ATP-Sensitive Potassium Channel (K_ATP) Openers. 5. Identification of 4-(N-Aryl)-Substituted Benzopyran Derivatives with High Selectivity

  摘要：

  This paper describes our studies aimed at the discovery of structurally distinct analogs of the cardioprotective K-ATP Opener BMS-180448 (2) with improved selectivity for the ischemic myocardium. The starting compound 6, derived from the indole analog 4, showed good cardioprotective potency and excellent selectivity compared to 2 and the first-generation K-ATP opener cromakalim (1). The structure-activity studies indicate that increasing the size of the alkyl ester leads to diminished potency as does its replacement with a variety of other groups (nitrile, methyl sulfone). Replacement of the ethyl ester of 6 with an imidazole gave the best compound 3 (BMS-191095) of this series which maintains the potency and selectivity of its predecessor 6. The results described in this publication further support that there is no correlation between vasorelaxant and cardioprotective potencies of K-ATP openers. Compound 3 is over 20- and 4000-fold more selective far the ischemic myocardium than 2 and cromakalim (1), respectively. The selectivity for the ischemic myocardium is achieved by reduction of vasorelaxant potency rather than enhancement in antiischemic potency. As for cromakalim (1) and 2, the cardioprotective effects of compound 3 are inhibited by cotreatment with the K-ATP blocker glyburide, indicating that the K-ATP Opening is involved in its mechanism of cardioprotection With its good oral bioavailability (47%) and plasma elimination half life (3 h) in rats, compound 3 offers an excellent candidate to investigate the role of residual vasorelaxant potency of 2 toward its cardioprotective activity in vivo.

  DOI：

  10.1021/jm9605905
• 作为产物：
  描述：

  苯胺 、 2-咪唑甲醛 以 甲醇 为溶剂， 反应 12.0h， 以95%的产率得到N-((1H-imidazol-2-yl)methylene)aniline
  参考文献：
  名称：

  Alteration of steric hindrance modulates glutathione resistance and cytotoxicity of three structurally related Ru^II-p-cymene complexes

  摘要：

  三种结构相关的基于咪唑席夫碱的Ru^II-p-芳烃配合物表现出立体位阻影响、缺氧反应、细胞周期阻滞以及对谷胱甘肽的抵抗力。这些配合物表现出抗转移和抗血管生成的效果。

  DOI：

  10.1039/c5dt04781a

文献信息

• ATP7B Binds Ruthenium(II) <i>p</i>-Cymene Half-Sandwich Complexes: Role of Steric Hindrance and Ru–I Coordination in Rescuing the Sequestration
  作者：Kallol Purkait、Ruturaj、Arindam Mukherjee、Arnab Gupta

  DOI：10.1021/acs.inorgchem.9b02780

  日期：2019.11.18

  Ruthenium(II/III) complexes are predicted to be efficient alternatives to platinum drug-resistant cancers but have never been investigated for sequestration and efflux by Cu-ATPases (ATP7A or ATP7B) overexpressed in resistant cancer cells, although a major cause of platinum drug resistance is found to be sequestration of platinum chemotherapeutic agents by thiol donors glutathione (GSH) or the Cys-X-X-Cys

  钌 (II/III) 配合物预计是铂类耐药癌症的有效替代品，但从未研究过在耐药癌细胞中过度表达的 Cu-ATP 酶（ATP7A 或 ATP7B）的螯合和外排，尽管铂类药物的主要原因发现耐药性是硫醇供体谷胱甘肽（GSH）或胞质溶胶中Cu-ATP酶中的Cys-XX-Cys（CXXC）基序对铂化疗剂的隔离。在这里，我们首次展示了 ATP7B 有效地螯合钌 (II) η6-p-伞花烃复合物。我们提出了七种配合物，[RuII(η6-p-cym)(L)X](PF6) (1-7; L = L1-L3, X = Cl, Br, and I)，其中两种通过细胞硫醇，谷胱甘肽（GSH）。结果表明，Ru-I 配位和适度的空间因子增加了对 GSH 和 CXXC 基序的抗性。RuII-I 配位的 3 和 7 显示出对 ATP7B 螯合的抗性。3 显示对 GSH 的最高抗性，并且不会触发 ATP7B 在肝癌细胞系中的运输。它逃避