1,3-dioxo-4-phenyl-2H-pyrrolo<3,4-c>quinoline | 29202-73-1

• 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: 1,3-dioxo-4-phenyl-2H-pyrrolo<3,4-c>quinoline
• 英文别名: 4-phenylpyrrolo[3,4-c]quinoline-1,3(2H)-dione；4-phenyl-pyrrolo[3,4-c]quinoline-1,3-dione；2-Phenylchinolin-3,4-dicarboxamid；4-Phenylpyrrolo[3,4-c]quinoline-1,3-dione
• CAS: 29202-73-1
• 化学式: C₁₇H₁₀N₂O₂
• 分子量: 274.279
• InChiKey: HXVXZDICSQQUKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 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) 、 1,3-dioxo-4-phenyl-2H-pyrrolo<3,4-c>quinoline 以 乙醇 、 水 为溶剂， 反应 18.0h， 以14%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：

  3-amino-2-phenylquinoline-4-carboxylic acid 在 氢溴酸 、 copper(I) bromide 、 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.42h， 生成 1,3-dioxo-4-phenyl-2H-pyrrolo<3,4-c>quinoline
  参考文献：
  名称：

  3-卤-2-苯基喹啉-4-羧酸的新型合成

  摘要：

  通过一种新颖的方法，以高收率获得了3-氯和3-溴-2-苯基喹啉-4-羧酸，需要合成3-氨基中间体，然后用氯或溴取代氨基。桑德迈尔反应。

  DOI：

  10.1002/jhet.5570340235

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.
• A novel synthesis of 3-halo-2-phenylquinoline-4-carboxylic acids
  作者：Luca F. Raveglia、Giuseppe A. M. Giardina、Mario Grugni、Roberto Rigolio、Carlo Farina

  DOI：10.1002/jhet.5570340235

  日期：1997.3

  3-bromo-2-phenylquinoline-4-carboxylic acids were obtained in good yields through a novel procedure, entailing the synthesis of the 3-amino intermediate and the subsequent replacement of the amino group with chlorine or bromine, according to the Sandmeyer reaction.

  通过一种新颖的方法，以高收率获得了3-氯和3-溴-2-苯基喹啉-4-羧酸，需要合成3-氨基中间体，然后用氯或溴取代氨基。桑德迈尔反应。