(7-chloroquinolin-4-yl)(2-dimethylaminomethylruthenocen-1-ylmethyl)amine | 552298-96-1

• 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: (7-chloroquinolin-4-yl)(2-dimethylaminomethylruthenocen-1-ylmethyl)amine
• 英文别名: ruthenoquine；7-chloro-N-[[2-[(dimethylamino)methyl]cyclopenta-2,4-dien-1-yl]methyl]quinolin-4-amine;cyclopenta-1,3-diene;ruthenium(2+)
• CAS: 552298-96-1
• 化学式: C₂₃H₂₄ClN₃Ru
• 分子量: 478.987
• InChiKey: QAUJPGMQNKFDDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (7-chloroquinolin-4-yl)(2-dimethylaminomethylruthenocen-1-ylmethyl)amine 、 乙酸酐 反应 0.08h， 以51%的产率得到7-chloro-4-(2-(acetoxymethyl)ruthenocenylmethylamino)quinoline
  参考文献：
  名称：

  有机钌氨基喹啉-三恶烷杂化物的合成及其抗恶性疟原虫的活性及其对正常哺乳动物细胞的毒性

  摘要：

  摘要合成了在单个分子结构中包含钌茂金属，4-氨基喹啉和1,2,4-三恶烷的新杂化化合物5，并评估了其抗疟潜力。为了确定杂种5的每个成分的作用，与氯喹，青蒿素（一种不含氨基喹啉的钌茂茂-三恶烷化合物9）相比，已测定了其对恶性疟原虫抗氯喹和氯喹敏感菌株的抗疟活性。，前体三恶烷酮4和三恶烷二聚体10。Hybrid 5在中低纳摩尔浓度IC 50中显示出高抗疟活性范围广，对健康哺乳动物细胞的细胞毒性低，这转化为良好的选择性指标。5的效力始终高于氯喹，不含母体的三恶烷和化合物9（结构中间体，特征在于钌茂金属部分键合到三恶烷上，但缺少氨基喹啉）的效力。这些结果证实了我们的假设，即单个分子中氨基喹啉，钌烯基部分和三恶烷的结合提供了增强的抗血浆活性，并突显了杂化化合物作为一种值得进一步关注的策略。 图形概要

  DOI：

  10.1007/s00044-016-1769-6
• 作为产物：
  描述：

  4,7-二氯喹啉 、 2-dimethylaminomethylruthenocen-1-ylmethylamine 在 Na₂CO₃ 、 triethylamine 作用下， 以 further solvent(s) 为溶剂， 以44%的产率得到(7-chloroquinolin-4-yl)(2-dimethylaminomethylruthenocen-1-ylmethyl)amine
  参考文献：
  名称：

  Synthesis and antimalarial activity in vitro of new ruthenocene–chloroquine analogues

  摘要：

  报道了新化合物 (7-氯喹啉-4-基)(2-二甲氨基甲基钌烯-1-基甲胺) 3 和 N-(7-氯喹啉-4-基)-N'-(2-二甲氨基甲基钌烯-1-基甲胺)乙烯-1,2-二胺 5 的合成。将这些反应与之前报告的类铁烯化合物的制备进行了比较。反应的关键步骤是通过在二乙醚中用 t-BuLi 去质子化二甲氨基甲基钌烯，选择性合成 2-二甲氨基甲基钌烯羧醛 10，随后加入 DMF。此外，还制备了 1'-二甲氨基甲基钌烯羧醛 11，意外合成了 1,1'-同分异构体 (7-氯喹啉-4-基)(1'-二甲氨基甲基钌烯-1-基甲胺) 17 和 N-(7-氯喹啉-4-基)-N'-(1'-二甲氨基甲基钌烯-1-基甲胺)乙烯-1,2-二胺 18。报道了化合物 3 和 17·H2O 的 X 射线晶体和分子结构。4-氨基喹啉配合物在体外对青蒿素敏感和耐药型的恶性疟原虫菌株表现出高效性；这些结果与类铁烯化合物的结果进行了比较。

  DOI：

  10.1039/b205432a

文献信息

• Statistical Methodology for the Detection of Small Changes in Distances by EXAFS: Application to the Antimalarial Ruthenoquine
  作者：Emmanuel Curis、Faustine Dubar、Ioannis Nicolis、Simone Bénazeth、Christophe Biot

  DOI：10.1021/jp301811r

  日期：2012.6.14

  Antimalarial compounds ruthenoquine and methylruthenoquine were studied by X-ray absorption spectroscopy both in solid state and in solution, in normal (aqueous or CH2Cl2 solutions) and oxidative (aqueous solution with H2O, either equimolar or in large excess) conditions, to detect small changes in the coordination sphere of the ruthenium atom. Since changes in the EXAFS spectra of these compounds are quite subtle, a complete procedure was developed to assess the different sources of uncertainties in fitted structural parameters, including the use of multivariate statistic methods for simultaneous comparison of edge energy correction Delta E-0 and distances, which can take into account the very strong correlation between these two parameters. Factors limiting the precision of distance determination depend on the recording mode. In transmission mode, the main source of uncertainty is the data reduction process, whereas in fluorescence mode, experimental noise is the main source of variability in the fitted parameters. However, it was shown that the effects of data reduction are systematic and almost identical for all compounds; hence, they can be ignored when comparing distances. Consequently, for both fluorescence and transmission recorded spectra, experimental noise is the limiting factor for distance comparisons, which leads to the use of statistical methods for comparing distances. Univariate methods, focusing on the distance only, are shown to be less powerful in detecting changes in distances than bivariate methods making a simultaneous comparison of Delta E-0 and distances. This bivariate comparison can be done either by using the Hotel ling's T-2 test or by using a graphical comparison of Monte Carlo simulation results, We have shown that using these methods allows for the detection of very subtle changes in distances. When applied to ruthenoquine compounds, it suggests that the implication of the nonbinding doublet of the aminoquine nitrogen in either protonation or methylation enhances the tilt of the two cyclopentadienyls. It also suggests that ruthenoquine and methylruthenoquine are, at least partially, oxidized in the presence of H2O2, with a small decrease in the Ru-C bond length and increase in the edge energy.