7-((4-(phenylsulfonyl)piperazin-1-yl)methyl)quinolin-8-ol | 1196448-93-7

• 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: 7-((4-(phenylsulfonyl)piperazin-1-yl)methyl)quinolin-8-ol
• 英文别名: 7-[[4-(Benzenesulfonyl)piperazin-1-yl]methyl]quinolin-8-ol
• CAS: 1196448-93-7
• 化学式: C₂₀H₂₁N₃O₃S
• 分子量: 383.471
• InChiKey: FUJVDKOTZSYCQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  8-羟基喹啉 、 聚合甲醛 、 1-苯磺酰基哌嗪 以 乙醇 为溶剂， 生成 7-((4-(phenylsulfonyl)piperazin-1-yl)methyl)quinolin-8-ol
  参考文献：
  名称：

  Synthesis and pharmacological exploitation of clioquinol-derived copper-binding apoptosis inducers triggering reactive oxygen species generation and MAPK pathway activation

  摘要：

  In the present study, we carried out Mannich-type reaction to synthesize clioquinol-derived 7-methylarylsulfonylpiperazine analogs with improved growth-inhibitory effects. 11 bearing 5-nitro group on the quinoline ring exhibited 26-fold more potent than that of clioquinol against HeLa cells with a GI(50) value of 0.71 mu M. In addition, 11 revealed synergistic effects on the growth inhibition of HeLa cells with GI(50) values of 0.65, 0.25, and 0.06 mu M in the presence of 1, 10, and 50 mu M copper, respectively. Consistent to the clioquinol-mediated apoptosis, mechanistic study indicates that 9- and 11-induced growth inhibition is attributed to caspase-dependent pathway. Detection of reactive oxygen species in response to clioquinol, 9 and 11 confirmed that ROS was dramatically stimulated in the presence of copper and partially abolished upon treatment of 1 mM tempol. Further study indicated that 9- and 11-mediated induction of oxidative stress by ROS generation resulted in the activation MAPK pathway. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.054

文献信息

• DNA METHYLATION INHIBITORS
  申请人：Chen Ching-Shih

  公开号：US20120157465A1

  公开（公告）日：2012-06-21

  A number of DNA methylation inhibitors are described. The DNA methylation inhibitors were identified using a two-component enhanced green fluorescent protein reporter system to screen a compound library containing procainamide derivatives. The DNA methylation inhibitors can be used for cancer therapy and prevention.
• US8546397B2
  申请人：——

  公开号：US8546397B2

  公开（公告）日：2013-10-01
• [EN] DNA METHYLATION INHIBITORS<br/>[FR] INHIBITEURS DE MÉTHYLATION DE L'ADN
  申请人：UNIV OHIO STATE RES FOUND

  公开号：WO2012087889A2

  公开（公告）日：2012-06-28

  A number of DNA methylation inhibitors are described. The DNA methylation inhibitors were identified using a two-component enhanced green fluorescent protein reporter system to screen a compound library containing procainamide derivatives. The DNA methylation inhibitors can be used for cancer therapy and prevention.
• Synthesis and pharmacological exploitation of clioquinol-derived copper-binding apoptosis inducers triggering reactive oxygen species generation and MAPK pathway activation
  作者：Hui-Ling Chen、Chun-Yi Chang、Hsun-Tzu Lee、Hua-Hsuan Lin、Pei-Jung Lu、Chia-Ning Yang、Chung-Wai Shiau、Arthur Y. Shaw

  DOI：10.1016/j.bmc.2009.08.054

  日期：2009.10

  In the present study, we carried out Mannich-type reaction to synthesize clioquinol-derived 7-methylarylsulfonylpiperazine analogs with improved growth-inhibitory effects. 11 bearing 5-nitro group on the quinoline ring exhibited 26-fold more potent than that of clioquinol against HeLa cells with a GI(50) value of 0.71 mu M. In addition, 11 revealed synergistic effects on the growth inhibition of HeLa cells with GI(50) values of 0.65, 0.25, and 0.06 mu M in the presence of 1, 10, and 50 mu M copper, respectively. Consistent to the clioquinol-mediated apoptosis, mechanistic study indicates that 9- and 11-induced growth inhibition is attributed to caspase-dependent pathway. Detection of reactive oxygen species in response to clioquinol, 9 and 11 confirmed that ROS was dramatically stimulated in the presence of copper and partially abolished upon treatment of 1 mM tempol. Further study indicated that 9- and 11-mediated induction of oxidative stress by ROS generation resulted in the activation MAPK pathway. (C) 2009 Elsevier Ltd. All rights reserved.