3-(1-methyl-1H-imidazol-4-yl)-2-oxo-4-phenyl-1,2-dihydro-quinoline-6-carbonitrile | 835881-04-4

• 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: 3-(1-methyl-1H-imidazol-4-yl)-2-oxo-4-phenyl-1,2-dihydro-quinoline-6-carbonitrile
• 英文别名: 3-(1-methylimidazol-4-yl)-2-oxo-4-phenyl-1H-quinoline-6-carbonitrile
• CAS: 835881-04-4
• 化学式: C₂₀H₁₄N₄O
• 分子量: 326.357
• InChiKey: GGXQPHJRIPPTEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  70.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-Chloro-3-(1-methylimidazol-4-yl)-4-phenylquinoline-6-carbonitrile 在 乙酸铵 、 溶剂黄146 作用下， 生成 3-(1-methyl-1H-imidazol-4-yl)-2-oxo-4-phenyl-1,2-dihydro-quinoline-6-carbonitrile
  参考文献：
  名称：

  Synthesis and evaluation of novel 3,4,6-substituted 2-quinolones as FMS kinase inhibitors

  摘要：

  A series of 3,4,6-substituted 2-quinolones has been synthesized and evaluated as inhibitors of the kinase domain of macrophage colony-stimulating factor-1 receptor (FMS). The fully optimized compound, 4-(4-ethyl-phenyl)-3-(2-methyl-3H-imidazol-4yl)-2-quinolone-6-carbonitrile 21b, has an IC50 of 2.5 nM in an in vitro assay and 5.0 nM in a bone marrow-derived macrophage cellular assay. Inhibition of FMS signaling in vivo was also demonstrated in a mouse pharmacodynamic model. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.088

文献信息

• Quinolinone derivatives as inhibitors of c-fms kinase
  申请人：Wall J. Mark

  公开号：US20050049274A1

  公开（公告）日：2005-03-03

  The invention is directed to compounds of Formulae I and II: wherein R 1 , R 2 , R 3 , R 5 , R 6 , Y 1 , Y 2 , Y 3 , Y 4 and X are set forth in the specification, as well as solvates, hydrates, tautomers or pharmaceutically acceptable salts thereof, that inhibit protein tyrosine kinases, especially c-fms kinase.

  本发明涉及公式I和II的化合物：其中R1、R2、R3、R5、R6、Y1、Y2、Y3、Y4和X如规范中所示，以及其溶剂化物、水合物、互变异构体或药学上可接受的盐，它们能够抑制蛋白酪氨酸激酶，特别是c-fms激酶。
• QUINOLINONE DERIVATIVES AS INHIBITORS OF C-FMS KINASE
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP1660087A2

  公开（公告）日：2006-05-31
• US7326788B2
  申请人：——

  公开号：US7326788B2

  公开（公告）日：2008-02-05
• [EN] QUINOLINONE DERIVATIVES AS INHIBITORS OF C-FMS KINASE<br/>[FR] DERIVES DE QUINOLINONE EN TANT QU'INHIBITEURS DE C-FMS KINASE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2005009967A2

  公开（公告）日：2005-02-03

  The invention is directed to compounds of Formulae I and II, wherein R1, R2, R3, R5, R6, Y1, Y2, Y3, Y4 and X are set forth in the specification, as well as solvates, hydrates, tautomers or pharmaceutically acceptable salts thereof, that inhibit protein tyrosine kinases, especially c-fms kinase.
• Synthesis and evaluation of novel 3,4,6-substituted 2-quinolones as FMS kinase inhibitors
  作者：Mark J. Wall、Jinsheng Chen、Sanath Meegalla、Shelley K. Ballentine、Kenneth J. Wilson、Renee L. DesJarlais、Carsten Schubert、Margery A. Chaikin、Carl Crysler、Ioanna P. Petrounia、Robert R. Donatelli、Edward J. Yurkow、Lisa Boczon、Marie Mazzulla、Mark R. Player、Raymond J. Patch、Carl L. Manthey、Christopher Molloy、Bruce Tomczuk、Carl R. Illig

  DOI：10.1016/j.bmcl.2008.01.088

  日期：2008.3

  A series of 3,4,6-substituted 2-quinolones has been synthesized and evaluated as inhibitors of the kinase domain of macrophage colony-stimulating factor-1 receptor (FMS). The fully optimized compound, 4-(4-ethyl-phenyl)-3-(2-methyl-3H-imidazol-4yl)-2-quinolone-6-carbonitrile 21b, has an IC50 of 2.5 nM in an in vitro assay and 5.0 nM in a bone marrow-derived macrophage cellular assay. Inhibition of FMS signaling in vivo was also demonstrated in a mouse pharmacodynamic model. (c) 2008 Elsevier Ltd. All rights reserved.