(R)-1-(pyridin-2-ylmethyl)pyrrolidine-2-carboxylic acid | 1414863-06-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-1-(pyridin-2-ylmethyl)pyrrolidine-2-carboxylic acid
• 英文别名: (R)-N-(pyridin-2-ylmethyl)proline；(2R)-1-(pyridin-2-ylmethyl)pyrrolidine-2-carboxylic acid
• CAS: 1414863-06-1
• 化学式: C₁₁H₁₄N₂O₂
• 分子量: 206.244
• InChiKey: JXAKWFRDECJWGV-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氯化铑(三水) 、 (R)-1-(pyridin-2-ylmethyl)pyrrolidine-2-carboxylic acid 、 1,3-dioxo-4-phenyl-2H-pyrrolo<3,4-c>quinoline 以 乙醇 、 水 为溶剂， 反应 18.0h， 以28%的产率得到
  参考文献：
  名称：

  Cyclometalated phenylquinoline rhodium complexes as protein kinase inhibitors

  摘要：

  A new metal-containing scaffold for the generation of rhodium(III)-based protein kinase inhibitors is introduced in which the pharmacophore ligand 4-phenylpyrrolo[3,4-c]quinoline-1,3(2H)-dione is designed to form two hydrogen bonds with the hinge region of the ATP-binding site. The phenylquinoline ligand binds to rhodium(III) in a cyclometalated fashion by coordinating to the quinoline nitrogen and forming a covalent bond to a carbon atom of the phenyl substituent. Additional acyclic tridentate ligands were used to control the relative stereochemistry, whereas a chiral proline-derived tridentate ligand was employed for the asymmetric synthesis of single enantiomers. Finally, protein kinase profiling and inhibition data confirmed that the new rhodium(III)-phenylquinoline scaffold is suitable for the generation of selective protein kinase inhibitors. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.04.035

文献信息

• Correlation between the Stereochemistry and Bioactivity in Octahedral Rhodium Prolinato Complexes
  作者：Rajathees Rajaratnam、Elisabeth K. Martin、Markus Dörr、Klaus Harms、Angela Casini、Eric Meggers

  DOI：10.1021/acs.inorgchem.5b01349

  日期：2015.8.17

  octahedral metal complexes constitutes a key challenge that needs to be overcome in order to fully exploit the structural properties of octahedral metal complexes for applications in the fields of catalysis, materials sciences, and life sciences. Herein, we describe the application of a proline-based chiral tridentate ligand to decisively control the coordination mode of an octahedral rhodium(III) complex

  控制八面体金属配合物的相对和绝对构型是一个关键的挑战，必须充分克服八面体金属配合物的结构特性，才能在催化，材料科学和生命科学领域中应用。在这里，我们描述了基于脯氨酸的手性三齿配体的应用，以决定性地控制八面体铑（III）配合物的配位模式。我们证明了合成对映异构体之间的镜像关系和非对映异构体之间的差异。此外，我们证明，使用已建立的吡啶并咔唑药效基团配体作为有机金属配合物的一部分，相对手性环境（如蛋白激酶）在金属上相对和绝对立体化学的重要性。蛋白激酶分析和抑制数据证实，尽管具有相同的构成，但基于脯氨酸的对映纯铑（III）络合物尽管选择性明确，但它们的选择性性质差异很大。此外，已经显示出两种示例性化合物在离体大鼠肝脏模型中诱导不同的毒性作用。
• Cyclometalated phenylquinoline rhodium complexes as protein kinase inhibitors
  作者：Stefan Mollin、Sebastian Blanck、Klaus Harms、Eric Meggers

  DOI：10.1016/j.ica.2012.04.035

  日期：2012.12

  A new metal-containing scaffold for the generation of rhodium(III)-based protein kinase inhibitors is introduced in which the pharmacophore ligand 4-phenylpyrrolo[3,4-c]quinoline-1,3(2H)-dione is designed to form two hydrogen bonds with the hinge region of the ATP-binding site. The phenylquinoline ligand binds to rhodium(III) in a cyclometalated fashion by coordinating to the quinoline nitrogen and forming a covalent bond to a carbon atom of the phenyl substituent. Additional acyclic tridentate ligands were used to control the relative stereochemistry, whereas a chiral proline-derived tridentate ligand was employed for the asymmetric synthesis of single enantiomers. Finally, protein kinase profiling and inhibition data confirmed that the new rhodium(III)-phenylquinoline scaffold is suitable for the generation of selective protein kinase inhibitors. (C) 2012 Elsevier B.V. All rights reserved.