5,7-二硝基-3-苯基-2-氯喹喔啉 | 1010857-57-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 5,7-二硝基-3-苯基-2-氯喹喔啉
• 英文名称: 5,7-dinitro-3-phenyl-2-chloroquinoxaline
• 英文别名: 2-Chloro-5,7-dinitro-3-phenylquinoxaline
• CAS: 1010857-57-4
• 化学式: C₁₄H₇ClN₄O₄
• 分子量: 330.687
• InChiKey: VJAFBWDNHMPUSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4,5-三甲氧基苄胺 、 5,7-二硝基-3-苯基-2-氯喹喔啉 以 丙醇 为溶剂， 反应 1.0h， 以95%的产率得到5,7-dinitro-3-phenyl-2-[(3,4,5-trimethoxybenzyl)amino]quinoxaline
  参考文献：
  名称：

  Synthesis and in vitro antitumor activity of new quinoxaline derivatives

  摘要：

  A series of novel 5,7-diamino-3-phenyl-2-benzylamino, 2-phenoxy, and 2-thiophenyl substituted quinoxalines has been designed, synthesized and evaluated for their in vitro antitumor activity towards cell lines of nine different types of human cancers. Some of these compounds exhibited inhibitory effects on the growth of a wide range of cancer cell lines generally at 10(-6) M, in some cases at 10(-7) M and 10(-8) M concentrations. Within this series the benzylamino quinoxaline derivatives 1b-7b were the most active, whereas compound 2c showed the highest MG_MD value (-5.66). (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.07.025
• 作为产物：
  描述：

  5,7-dinitro-3-phenylquinoxalin-2(1H)one 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 反应 1.67h， 以90%的产率得到5,7-二硝基-3-苯基-2-氯喹喔啉
  参考文献：
  名称：

  Synthesis of N-(5,7-diamino-3-phenyl-quinoxalin-2-yl)-3,4,5-substituted anilines and N-[4[(5,7-diamino-3-phenylquinoxalin-2-yl)amino]benzoyl]-l-glutamic acid diethyl ester: Evaluation of in vitro anti-cancer and anti-folate activities

  摘要：

  Several diamino quinoxalines were designed, synthesized and evaluated as anti-tumor agents. Two compounds showed the most potent cytotoxic activities against the leukemia CCRF-CEM cell line (GI(50) < 0-01 mu M) and the ovarian cancer cell line OVCAR-4 (GI(50) = 0.03 mu M), respectively, with comparable/better activities than Methotrexate (MTX). Docking calculations of the complexes of hDHFR with the most active compounds identified the binding mode of the described molecules with respect to MTX. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.03.035

文献信息

• Synthesis and in vitro antitumor activity of new quinoxaline derivatives
  作者：Paola Corona、Antonio Carta、Mario Loriga、Gabriella Vitale、Giuseppe Paglietti

  DOI：10.1016/j.ejmech.2008.07.025

  日期：2009.4

  A series of novel 5,7-diamino-3-phenyl-2-benzylamino, 2-phenoxy, and 2-thiophenyl substituted quinoxalines has been designed, synthesized and evaluated for their in vitro antitumor activity towards cell lines of nine different types of human cancers. Some of these compounds exhibited inhibitory effects on the growth of a wide range of cancer cell lines generally at 10(-6) M, in some cases at 10(-7) M and 10(-8) M concentrations. Within this series the benzylamino quinoxaline derivatives 1b-7b were the most active, whereas compound 2c showed the highest MG_MD value (-5.66). (C) 2008 Elsevier Masson SAS. All rights reserved.
• Synthesis of N-(5,7-diamino-3-phenyl-quinoxalin-2-yl)-3,4,5-substituted anilines and N-[4[(5,7-diamino-3-phenylquinoxalin-2-yl)amino]benzoyl]-l-glutamic acid diethyl ester: Evaluation of in vitro anti-cancer and anti-folate activities
  作者：Paola Corona、Mario Loriga、M. Paola Costi、Stefania Ferrari、Giuseppe Paglietti

  DOI：10.1016/j.ejmech.2007.03.035

  日期：2008.1

  Several diamino quinoxalines were designed, synthesized and evaluated as anti-tumor agents. Two compounds showed the most potent cytotoxic activities against the leukemia CCRF-CEM cell line (GI(50) < 0-01 mu M) and the ovarian cancer cell line OVCAR-4 (GI(50) = 0.03 mu M), respectively, with comparable/better activities than Methotrexate (MTX). Docking calculations of the complexes of hDHFR with the most active compounds identified the binding mode of the described molecules with respect to MTX. (C) 2007 Elsevier Masson SAS. All rights reserved.