C6H4C2NH(C5H3N)C4O2N(benzyl) | 1234890-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: C6H4C2NH(C5H3N)C4O2N(benzyl)
• 英文别名: 4-Benzyl-4,11,14-triazapentacyclo[11.7.0.02,6.07,12.015,20]icosa-1,6,8,10,12,15,17,19-octaene-3,5-dione
• CAS: 1234890-16-4
• 化学式: C₂₄H₁₅N₃O₂
• 分子量: 377.402
• InChiKey: GHAAQZNVODXUKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  66.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  RhCl3(tetrahydrothiophen)3 、 C6H4C2NH(C5H3N)C4O2N(benzyl) 以 乙醇 、 水 为溶剂， 以71%的产率得到
  参考文献：
  名称：

  作为蛋白质激酶抑制剂的吡啶并咔唑-铑 (III) 复合物

  摘要：

  惰性金属配合物是设计酶抑制剂的复杂结构支架。尽管我们实验室以前的工作主要基于钌 (II)，但本研究评估了 +3 氧化态的铑作为设计惰性金属基酶抑制剂的结构中心的适用性。基于我们建立的 staurosporine 启发的金属吡啶并咔唑支架，开发了方便合成铑 (III)-吡啶并咔唑复合物的策略，并将其应用于蛋白激酶抑制剂的合成。通过 X 射线晶体学研究了几种铑配合物的结构。稳定性研究证实了这种铑配合物在生物相关条件下的高动力学惰性，例如存在毫摩尔浓度的硫醇。最后，发现了一种极其有效的皮摩尔铑蛋白激酶 Pim1 抑制剂。因此，可以得出结论，铑 (III) 扩展了设计具有生物活性的惰性金属配合物的工具箱。

  DOI：

  10.1002/ejic.201101175
• 作为产物：
  描述：

  以 甲苯 为溶剂， 以78%的产率得到C6H4C2NH(C5H3N)C4O2N(benzyl)
  参考文献：
  名称：

  应变促进的叠氮化物-炔烃环加成反应与钌（II）-叠氮基配合物

  摘要：

  研究了示例性的钌（II）-叠氮基络合物在室温和低叠氮化物和炔烃浓度下对未活化的，电子不足的以及对应变活化的炔烃的反应性。在这种条件下，即使在铜（I）催化条件下，未活化的末端炔烃和内部炔烃也无法反应。相反，正如预期的那样，使用缺电子的乙炔二羧酸二甲酯（DMAD）作为双极性亲和剂，观察到了快速的环加成反应。由于DMAD和相关的炔丙基酯是出色的Michael受体，因此不适合生物学应用，因此我们研究了叠氮基络合物与环辛炔（OCT），双环[6.1.0] non-4-yne（BCN）衍生物的环加成反应性，和氮杂二苯并环辛炔（ADIBO）。虽然在应变较小的环辛炔OCT的情况下未观察到反应，但应变较大的环辛炔BCN和ADIBO容易与叠氮基络合物反应，提供了相应的稳定的三唑并合物，可通过常规硅胶柱色谱纯化。获得了ADIBO环加合物的X射线晶体结构，并验证了形成的1,2,3-三唑并配体通过中心N2原子配位金属

  DOI：

  10.1002/chem.201302502

文献信息

• Iridium Complex with Antiangiogenic Properties
  作者：Alexander Wilbuer、Danielle H. Vlecken、Daan J. Schmitz、Katja Kräling、Klaus Harms、Christoph P. Bagowski、Eric Meggers

  DOI：10.1002/anie.201000682

  日期：——

  Identified as nanomolar and selective inhibitor of receptor protein kinase VEGFR3 (Flt4), the nontoxic and octahedrally coordinated IrIII complex 1 was synthesized by a stereoselective oxidative addition to a square‐planar coordinated IrI precursor. The arrows in the image indicate positions at which the blood vessel formation in a zebrafish model of angiogenesis has been hampered by 1.

  无毒且八面体配位的Ir III复合物1被鉴定为受体蛋白激酶VEGFR3（Flt4）的纳摩尔浓度和选择性抑制剂，是通过将立体选择性氧化加成到方形平面配位的Ir I前体中而合成的。图像中的箭头表示斑马鱼血管生成模型中的血管形成已受1阻碍的位置。
• P-donor ligand containing ruthenium half-sandwich complexes as protein kinase inhibitors
  作者：Craig Streu、Li Feng、Patrick J. Carroll、Jasna Maksimoska、Ronen Marmorstein、Eric Meggers

  DOI：10.1016/j.ica.2011.07.032

  日期：2011.11

  Metal complexes have emerged as promising and novel scaffolds for the design of enzyme inhibitors. Reported herein are the design, synthesis, and evaluation of protein kinase inhibition properties of pyridocarbazole half-sandwich complexes containing P-donor ligands. The nature of the monodentate P-donor ligand has a strong effect on protein kinase binding properties, most likely due to a direct interaction with the glycine-rich loop in the ATP-binding site. We furthermore discovered that PMe3 pyridocarbazole complexes are interesting lead structures for the design of potent inhibitors for the protein kinase TrkA for which we obtained a nanomolar organometallic inhibitor. (C) 2011 Elsevier B. V. All rights reserved.
• Octahedral rhodium(III) complexes as kinase inhibitors: Control of the relative stereochemistry with acyclic tridentate ligands
  作者：Stefan Mollin、Radostan Riedel、Klaus Harms、Eric Meggers

  DOI：10.1016/j.jinorgbio.2015.01.005

  日期：2015.7

  Octahedral metal complexes are attractive structural templates for the design of enzyme inhibitors as has been demonstrated, for example, with the development of metallo-pyridocarbazoles as protein kinase inhibitors. The octahedral coordination sphere provides untapped structural opportunities but at the same time poses the drawback of dealing with a large number of stereoisomers. In order to address this challenge of controlling the relative metal-centered configuration, the synthesis of rhodium(III) pyridocarbazole complexes with facially coordinating acyclic tridentate ligands was investigated. A strategy for the rapid synthesis of such complexes is reported, the diastereoselectivities of these reactions were investigated, the structure of several complexes were determined by X-ray crystallography, the high kinetic stability of such complexes in thiol-containing solutions was demonstrated in H-1-NMR experiments, and the protein kinase inhibition ability of this class of complexes was confirmed. It can be concluded that the use of multidentate ligands is currently maybe the most practical strategy to avoid a large number of possible stereoisomers in the course of exploiting octahedral coordination spheres as structural templates for the design of bioactive molecules. (C) 2015 Elsevier Inc. All rights reserved.
• US7488817B2
  申请人：——

  公开号：US7488817B2

  公开（公告）日：2009-02-10
• US7671046B2
  申请人：——

  公开号：US7671046B2

  公开（公告）日：2010-03-02