7-Chloro-3-(4-methoxyphenyl)-1,4-dioxido-quinoxaline-1,4-diium-2-carbonitrile | 1079038-69-9

• 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: 7-Chloro-3-(4-methoxyphenyl)-1,4-dioxido-quinoxaline-1,4-diium-2-carbonitrile
• 英文别名: 7-chloro-3-(4-methoxyphenyl)-1-oxido-4-oxoquinoxalin-4-ium-2-carbonitrile
• CAS: 1079038-69-9
• 化学式: C₁₆H₁₀ClN₃O₃
• 分子量: 327.727
• InChiKey: WWBXAHYRXSLRDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-氯苯并呋咱 3-氧化物 、 4-甲氧基苯甲酰基乙腈 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 7-Chloro-3-(4-methoxyphenyl)-1,4-dioxido-quinoxaline-1,4-diium-2-carbonitrile
  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

• Synthesis and structure–activity relationship of 3-phenylquinoxaline 1,4-di-N-oxide derivatives as antimalarial agents
  作者：Esther Vicente、Lidia M. Lima、Emily Bongard、Sarah Charnaud、Raquel Villar、Beatriz Solano、Asunción Burguete、Silvia Perez-Silanes、Ignacio Aldana、Livia Vivas

  DOI：10.1016/j.ejmech.2007.11.024

  日期：2008.9

  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.