2-羧基-3-苯基喹喔啉1,4-二氧化物 | 83579-75-3

• 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: 2-羧基-3-苯基喹喔啉1,4-二氧化物
• 英文名称: 1,4-Dioxy-3-phenyl-quinoxaline-2-carboxylic acid
• 英文别名: 1-Oxido-4-oxo-3-phenylquinoxalin-4-ium-2-carboxylic acid
• CAS: 83579-75-3
• 化学式: C₁₅H₁₀N₂O₄
• 分子量: 282.255
• InChiKey: JNYOUKCLQYIPCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-羧基-3-苯基喹喔啉1,4-二氧化物 以 甲苯 为溶剂， 生成 2-phenyl-quinoxaline-1,4-dioxide
  参考文献：
  名称：

  El-Abadelah, Mustafa M.; Anani, Ali A.; Khan, Zahida H., Heterocycles, 1982, vol. 19, # 9, p. 1663 - 1666

  摘要：

  DOI：
• 作为产物：
  描述：

  3-phenylquinoxaline-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 2-羧基-3-苯基喹喔啉1,4-二氧化物
  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

• EL-ABADELAH, M. M.;ANANI, A. A.;KHAN, Z. H., HETEROCYCLES, 1982, 19, N 9, 1663-1665
  作者：EL-ABADELAH, M. M.、ANANI, A. A.、KHAN, Z. H.

  DOI：——

  日期：——
• 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.
• El-Abadelah, Mustafa M.; Anani, Ali A.; Khan, Zahida H., Heterocycles, 1982, vol. 19, # 9, p. 1663 - 1666
  作者：El-Abadelah, Mustafa M.、Anani, Ali A.、Khan, Zahida H.

  DOI：——

  日期：——