3-[(4-methoxycarbonyl)phenyl]quinoxaline-2-carbonitrile 1,4-dioxide | 877791-59-8

• 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: 3-[(4-methoxycarbonyl)phenyl]quinoxaline-2-carbonitrile 1,4-dioxide
• 英文别名: Benzoic acid, 4-(3-cyano-1,4-dioxido-2-quinoxalinyl)-, methyl ester；methyl 4-(3-cyano-1-oxido-4-oxoquinoxalin-4-ium-2-yl)benzoate
• CAS: 877791-59-8
• 化学式: C₁₇H₁₁N₃O₄
• 分子量: 321.292
• InChiKey: BCDGPCSDPINDJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  96.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[(4-methoxycarbonyl)phenyl]quinoxaline-2-carbonitrile 1,4-dioxide 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 3-(4-Carboxyphenyl)-1-oxido-4-oxoquinoxalin-4-ium-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and structure–activity relationship of 3-phenylquinoxaline 1,4-di-N-oxide derivatives as antimalarial agents

  摘要：

  As a continuation of our research and with the aim of obtaining new antimalarial agents, new series of 3-phenylquinoxaline 1,4-di-N-oxide derivatives have been synthesized following the classical Beirut reaction. Antiplasmodial activity was evaluated in vitro against Plasmodium falciparum by the incorporation of [H-3]-hypoxanthine. Cytotoxicity was tested in KB cells by AlamarBlue assay. Twenty-one of the 60 compounds that were assayed against 3D7 (CQ-sensitive) showed enough activity to be also evaluated against K1 (CQ-resistant) strain. Ten of them were shown to be more active than chloroquine in the resistant strain. The most interesting compounds are 7-(methyl or methoxy)-3-(4'-fluoro or chloro)phenylquinoxaline-2-carbonitrile 1,4-di-N-oxides because of their low IC50 and their high SI shown for the K1 strain, making them valid new leads. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.11.024
• 作为产物：
  描述：

  苯并呋咱 、 4-(氰基乙酰)苯甲酸甲酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 3-[(4-methoxycarbonyl)phenyl]quinoxaline-2-carbonitrile 1,4-dioxide
  参考文献：
  名称：

  Synthesis and structure–activity relationship of 3-phenylquinoxaline 1,4-di-N-oxide derivatives as antimalarial agents

  摘要：

  As a continuation of our research and with the aim of obtaining new antimalarial agents, new series of 3-phenylquinoxaline 1,4-di-N-oxide derivatives have been synthesized following the classical Beirut reaction. Antiplasmodial activity was evaluated in vitro against Plasmodium falciparum by the incorporation of [H-3]-hypoxanthine. Cytotoxicity was tested in KB cells by AlamarBlue assay. Twenty-one of the 60 compounds that were assayed against 3D7 (CQ-sensitive) showed enough activity to be also evaluated against K1 (CQ-resistant) strain. Ten of them were shown to be more active than chloroquine in the resistant strain. The most interesting compounds are 7-(methyl or methoxy)-3-(4'-fluoro or chloro)phenylquinoxaline-2-carbonitrile 1,4-di-N-oxides because of their low IC50 and their high SI shown for the K1 strain, making them valid new leads. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.11.024

文献信息

• Zarranz, Belen; Jaso, Andres; Aldana, Ignacio, Arzneimittel-Forschung/Drug Research, 2005, vol. 55, # 12, p. 754 - 761
  作者：Zarranz, Belen、Jaso, Andres、Aldana, Ignacio、Monge, Antonio、Maurel, Severine、Deharo, Eric、Jullian, Valerie、Sauvain, Michel

  DOI：——

  日期：——