2-choloro-3-(4-methylphenylsulfonyl)quinoxaline | 948234-10-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-choloro-3-(4-methylphenylsulfonyl)quinoxaline
• 英文别名: 2-chloro-3-(4-methylphenylsulfonyl)quinoxaline；2-Chloro-3-(4-methylbenzenesulfonyl)quinoxaline；2-chloro-3-(4-methylphenyl)sulfonylquinoxaline
• CAS: 948234-10-4
• 化学式: C₁₅H₁₁ClN₂O₂S
• 分子量: 318.784
• InChiKey: HPYNAICIJNELED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  68.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-choloro-3-(4-methylphenylsulfonyl)quinoxaline 、 3-氨基苯酚 以 甲苯 为溶剂， 反应 12.0h， 以18%的产率得到2-(3-hydroxyphenylamino)-3-tosylquinoxaline
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2-arylamino-3-(arylsulfonyl)quinoxalines as PI3Kα inhibitors

  摘要：

  A series of novel 2-arylamino-3-(arylsulfonyl)quinoxalines was synthesized through a newly developed approach. All synthesized target compounds were screened for their cytotoxicities against cancer cell lines including PC3, A549, HCT116, HL60 and KB. Representative compounds with favorable cytotoxicities were tested for their PI3K alpha inhibitory activities. Among the synthesized target compounds, 17 (PI3K alpha IC50: 0.07 mu M) displayed the most potent cellular activities (IC50 values of 0.14 mu M, 0.07 mu M, 0.95 mu M and 0.05 mu M against PC3, A549, HCT116 and HL 60, respectively). (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.015
• 作为产物：
  描述：

  2,3-二羟基喹喔啉 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 乙醇 为溶剂， 反应 1.67h， 生成 2-choloro-3-(4-methylphenylsulfonyl)quinoxaline
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2-arylamino-3-(arylsulfonyl)quinoxalines as PI3Kα inhibitors

  摘要：

  A series of novel 2-arylamino-3-(arylsulfonyl)quinoxalines was synthesized through a newly developed approach. All synthesized target compounds were screened for their cytotoxicities against cancer cell lines including PC3, A549, HCT116, HL60 and KB. Representative compounds with favorable cytotoxicities were tested for their PI3K alpha inhibitory activities. Among the synthesized target compounds, 17 (PI3K alpha IC50: 0.07 mu M) displayed the most potent cellular activities (IC50 values of 0.14 mu M, 0.07 mu M, 0.95 mu M and 0.05 mu M against PC3, A549, HCT116 and HL 60, respectively). (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.015

文献信息

• Discovery of novel morpholino–quinoxalines as PI3Kα inhibitors by pharmacophore-based screening
  作者：Peng Wu、Yi Su、Xiaowen Liu、Jingying Yan、Yong Ye、Lei Zhang、Jianchao Xu、Shaoyu Weng、Yani Li、Tao Liu、Xiaowu Dong、Maotang Sun、Bo Yang、Qiaojun He、Yongzhou Hu

  DOI：10.1039/c2md00255h

  日期：——

  A pharmacophore model of PI3Kα inhibitors was built using the DiscoveryStudio 2.0 package. Pharmacophore-based screening (PBS) retrieved a series of novel morpholino–quinoxalines as PI3Kα inhibitors, as exemplified by 1a (PI3Kα IC50: 0.44 μM). All target compounds showed good in vitro cytotoxicity against tested human cell lines. A pharmacophore mapping analysis and docking study indicated that both the morpholino group and the sulfonyl group contributed significantly to the potent PI3Kα inhibitory activity and cytotoxicity of the compounds.

  利用 DiscoveryStudio 2.0 软件包建立了 PI3Kδ抑制剂的药理模型。药理筛选（PBS）发现了一系列新型吗啉喹喔啉类 PI3Kδ抑制剂，如 1a（PI3Kδ IC50：0.44 μM）。所有目标化合物都对测试的人体细胞系显示出良好的体外细胞毒性。药效图谱分析和对接研究表明，吗啉基团和磺酰基团对这些化合物的强效 PI3K δ 抑制活性和细胞毒性都有显著作用。
• Discovery of novel 2-piperidinol-3-(arylsulfonyl)quinoxalines as phosphoinositide 3-kinase α (PI3Kα) inhibitors
  作者：Peng Wu、Yi Su、Xiaowen Liu、Bo Yang、Qiaojun He、Yongzhou Hu

  DOI：10.1016/j.bmc.2012.03.026

  日期：2012.5

  A series of novel 2-aliphatic cyclic amine-3-(arylsulfonyl)quinoxalines was synthesized based on the structural features of a previously identified lead, WR1. The 2-piperidinol-3-(arylsulfonyl) quinoxalines, which showed excellent antitumor activities against five human cell lines, with inhibitory activities ranging from 0.34 to 2.32 mu M, proved to be a promising class of novel PI3K alpha inhibitors. The most potent compound 10d (WR23) showed an inhibitory IC50 value of 0.025 mu M against PI3K alpha and significant pAkt suppression effect. Molecular docking analysis was performed to determine possible binding modes between PI3K alpha and target compounds. (C) 2012 Elsevier Ltd. All rights reserved.