4-chloro-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinoline-3-carbonitrile | 423180-28-3

• 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: 4-chloro-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinoline-3-carbonitrile
• CAS: 423180-28-3
• 化学式: C₁₈H₂₀ClN₃O₂
• 分子量: 345.829
• InChiKey: XKONXPUSBPPOGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4-二氯-5-甲氧基苯胺 、 4-chloro-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinoline-3-carbonitrile 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 4-(2,4-二氯-5-甲氧基苯胺基)-6-甲氧基-7-[(1-甲基哌啶-4-基)甲氧基]喹啉-3-腈
  参考文献：
  名称：

  Investigation of the effect of varying the 4-anilino and 7-alkoxy groups of 3-quinolinecarbonitriles on the inhibition of Src kinase activity

  摘要：

  Several 7-alkoxy-4-anilino-3-quinolinecarbonitriles were synthesized and evaluated for Src kinase inhibitory activity. Optimal inhibition of both Src enzymatic and cellular activity was seen with analogues having a 2,4-dichloro-5-methoxyaniline group at C-4. Compound 18, which has a 1-methylpiperidinemethoxy group at C-7, showed in vivo activity in a xenograft model. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.001
• 作为产物：
  描述：

  香草酸甲酯 在 palladium on activated charcoal 正丁基锂 、 甲酸 、 氢气 、 硝酸 、 potassium carbonate 、 三氟乙酸 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 4-chloro-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinoline-3-carbonitrile
  参考文献：
  名称：

  Investigation of the effect of varying the 4-anilino and 7-alkoxy groups of 3-quinolinecarbonitriles on the inhibition of Src kinase activity

  摘要：

  Several 7-alkoxy-4-anilino-3-quinolinecarbonitriles were synthesized and evaluated for Src kinase inhibitory activity. Optimal inhibition of both Src enzymatic and cellular activity was seen with analogues having a 2,4-dichloro-5-methoxyaniline group at C-4. Compound 18, which has a 1-methylpiperidinemethoxy group at C-7, showed in vivo activity in a xenograft model. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.001

文献信息

• Process for the preparation of 7-substituted-3 quinolinecarbonitriles
  申请人：Wyeth Holdings Corporation

  公开号：US20030212276A1

  公开（公告）日：2003-11-13

  There is provided a process for the preparation of 7-substituted-3-quinolinecarbonitriles and intermediates useful in a process to prepare 7-substituted-3-quinolinecarbonitriles and pharmaceutically acceptable salts is described. Where 7-fluoro-4-oxo-1,4-dihydro-3-quinolinecarbonitrile is converted in three steps to 7-substituted-3-quinolinecarbonitriles which inhibit the action of certain protein kinases and are useful in the treatment of cancer.

  提供了一种制备7-取代-3-喹啉羰基腈和中间体的方法，该中间体在制备7-取代-3-喹啉羰基腈和药用可接受盐的过程中有用。将7-氟-4-氧代-1,4-二氢-3-喹啉羰基腈转化为7-取代-3-喹啉羰基腈，经过三个步骤，这些化合物抑制某些蛋白激酶的作用，并在癌症治疗中有用。
• [EN] PROCESS FOR THE PREPARATION OF 7-SUBSTITUTED-3-QUINOLINE AND 3-QUINOL-4-ONE CARBONITRILES<br/>[FR] PREPARATION DE 3-QUINOLINE ET DE 3-QUINOL- 4-ONE CARBONITRILES SUBSTITUES EN POSITION 7
  申请人：WYETH CORP

  公开号：WO2003093241A1

  公开（公告）日：2003-11-13

  There is provided a process for the preparation of 7-substituted-3-quinolinecarbonitriles and intermediates useful in a process to prepare 7-substituted-3-quinolinecarbonitriles and pharmaceutically acceptable salts is described. Where 7-fluoro-4-oxo-1,4-dihydro-3-quinolinecarbonitrile is converted in three steps to 7-substituted-3-quinolinecarbonitriles which inhibit the action of certain protein kinases and are useful in the treatment of cancer.

  提供了一种制备7-取代-3-喹啉羰基腈及其中间体的方法，该中间体可用于制备7-取代-3-喹啉羰基腈及其药用可接受盐的方法。其中，7-氟-4-氧代-1,4-二氢-3-喹啉羰基腈经过三步转化成为抑制某些蛋白激酶作用且用于治疗癌症的7-取代-3-喹啉羰基腈。
• 4-Substituted quinolines as antitumor agents
  申请人：Boyle Thomas Francis

  公开号：US20080027054A1

  公开（公告）日：2008-01-31

  The invention concerns compounds of formula (I), wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , R 9 , R 10 m, n, p, X, Y and Z have any meanings defined in the description, processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use as an anti-proliferative agent in the treatment of solid tumour disease.

  该发明涉及式(I)的化合物，其中R1、R2、R3、R4、R5、R6、R8、R9、R10、m、n、p、X、Y和Z的任何含义定义在说明中，它们的制备方法，包含它们的制药组合物，以及在制造用于治疗实体肿瘤疾病的抗增殖剂药物时使用它们的用途。
• PROCESS FOR THE PREPARATION OF 7-SUBSTITUTED-3-QUINOLINE AND 3-QUINOL-4-ONE CARBONITRILES
  申请人：Wyeth Holdings Corporation

  公开号：EP1499594A1

  公开（公告）日：2005-01-26
• US6780996B2
  申请人：——

  公开号：US6780996B2

  公开（公告）日：2004-08-24