3-(4-Fluorophenyl)-1,4-dioxido-7-(trifluoromethyl)quinoxaline-1,4-diium-2-carbonitrile | 1079038-88-2

• 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-Fluorophenyl)-1,4-dioxido-7-(trifluoromethyl)quinoxaline-1,4-diium-2-carbonitrile
• 英文别名: 3-(4-fluorophenyl)-1-oxido-4-oxo-7-(trifluoromethyl)quinoxalin-4-ium-2-carbonitrile
• CAS: 1079038-88-2
• 化学式: C₁₆H₇F₄N₃O₂
• 分子量: 349.244
• InChiKey: HYPPVQDTROHSCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-氟苯甲酰基乙腈 、 5-trifluoromethylbenzofuroxan 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 3-(4-Fluorophenyl)-1,4-dioxido-7-(trifluoromethyl)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

• Selective activity against Mycobacterium tuberculosis of new quinoxaline 1,4-di-N-oxides
  作者：Esther Vicente、Silvia Pérez-Silanes、Lidia M. Lima、Saioa Ancizu、Asunción Burguete、Beatriz Solano、Raquel Villar、Ignacio Aldana、Antonio Monge

  DOI：10.1016/j.bmc.2008.10.086

  日期：2009.1

  New series of 3-phenylquinoxaline 1,4-di-N-oxide with selective activity against Mycobacterium tuberculosis have been prepared and evaluated. Thirty-four of the seventy tested compounds showed an MIC value less than 0.2 mu g/mL, a value on the order of the MIC of rifampicin. Furthermore, 45% of the evaluated derivatives showed a good in vitro activity/toxicity ratio. The most active and selective compounds carry a fluorine atom in the quinoxaline 7-position or in the phenyl substituent para-position. In conclusion, the potency, low cytotoxicity and selectivity of these compounds make them valid lead compounds for synthesizing new analogues, particularly compound 7-methyl-3-(4'-fluoro) phenylquinoxaline-2-carbonitrile 1,4-di-N-oxide (MIC <0.2 mu g/mL and SI > 500). (C) 2008 Elsevier Ltd. All rights reserved.
• Anti-T. cruzi activities and QSAR studies of 3-arylquinoxaline-2-carbonitrile di-N-oxides
  作者：Esther Vicente、Pablo R. Duchowicz、Diego Benítez、Eduardo A. Castro、Hugo Cerecetto、Mercedes González、Antonio Monge

  DOI：10.1016/j.bmcl.2010.06.101

  日期：2010.8

  In a continuing effort to identify new active compounds for combating Chagas disease and other neglected diseases, our research group synthesized and evaluated 23 3-arylquinoxaline-2-carbonitrile di-N-oxides against Trypanosoma cruzi. Five of them presented IC50 values of the same magnitude as the standard drug Nifurtimox, making them valid as new lead compounds. The optimized molecular structures of 23 derivatives represented by 1497 types of DRAGON descriptors were subjected to linear regression analysis, and the derived QSAR was shown to be predictive. In this way, we achieved a rational guide for the proposal of new candidate structures whose activities still remain unknown. (C) 2010 Elsevier Ltd. All rights reserved.