2-benzyl-4-phenylpyrrolo[3,4-c]quinoline-1,3(2H)-dione | 1414863-00-5

• 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: 2-benzyl-4-phenylpyrrolo[3,4-c]quinoline-1,3(2H)-dione
• 英文别名: 2-Benzyl-4-phenylpyrrolo[3,4-c]quinoline-1,3-dione；2-benzyl-4-phenylpyrrolo[3,4-c]quinoline-1,3-dione
• CAS: 1414863-00-5
• 化学式: C₂₄H₁₆N₂O₂
• 分子量: 364.403
• InChiKey: NNOQZNSJRBEZHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  50.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(pyridin-2-ylmethyl)thio]acetic acid 、 氯化铑(三水) 、 2-benzyl-4-phenylpyrrolo[3,4-c]quinoline-1,3(2H)-dione 以 乙醇 、 水 为溶剂， 反应 18.0h， 以16%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
• 作为产物：
  描述：

  2-phenylquinoline-3,4-dicarboxylic acid 以 乙酸酐 为溶剂， 反应 6.0h， 生成 2-benzyl-4-phenylpyrrolo[3,4-c]quinoline-1,3(2H)-dione
  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

• 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.