5(6)-Ethoxycarbonyl-benzofuroxan | 39060-33-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: 5(6)-Ethoxycarbonyl-benzofuroxan
• 英文别名: 3-oxy-benzo[1,2,5]oxadiazole-5-carboxylic acid ethyl ester；Ethyl 3-oxido-2,1,3-benzoxadiazol-3-ium-5-carboxylate
• CAS: 39060-33-8
• 化学式: C₉H₈N₂O₄
• 分子量: 208.174
• InChiKey: LWNNTOUMKJKTKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  77.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5(6)-Ethoxycarbonyl-benzofuroxan 、 N-乙酰乙酰苯胺 在 C.I.酸性橙108 、 calcium chloride 作用下， 以 甲醇 为溶剂， 以22.4%的产率得到ethyl 2-phenylamide-3-methylquinoxaline-7-carboxylate 1,4-di-N-oxide
  参考文献：
  名称：

  Synthesis and in vitro evaluation of new ethyl and methyl quinoxaline-7-carboxylate 1,4-di-N-oxide against Entamoeba histolytica

  摘要：

  In our search for new antiamoebic agents, a new series of ethyl and methyl quinoxaline-7-carboxylate 1,4-di-N-oxide derivatives have been synthesized using the Beirut reaction. All compounds were characterized by spectroscopic techniques and elemental analysis. Antiamoebic activity was evaluated in vitro against Entamoeba histolytica strain HM1:IMSS by the microdilution method, and the structure-activity relationship was analyzed. We found that eleven quinoxaline derivatives showed greater activity than metronidazole and nitazoxanide with IC50 values in the range 1.99-0.35 mu M. Compounds T-001 and T-016 shows IC50 values of 1.41 and 1.47 mu M, respectively, with a value of selectivity index >60. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.036

文献信息

• <i>In vitro</i> and <i>In Vivo</i> Evaluation of Quinoxaline 1,4-di-N-oxide Against <i>Giardia lamblia</i>
  作者：Elizabeth Barbosa-Cabrera、Rosa Moo-Puc、Antonio Monge、Alma Delia Paz-González、Virgilio Bocanegra-García、Gildardo Rivera

  DOI：10.2174/1570180816666190618115854

  日期：2020.4.25

  Giardiasis is an important public health problem. However, its pharmacological treatment is limited mainly to two drugs, metronidazole and nitazoxanide. Objectives: Screening four series of esters (methyl, ethyl, isopropyl and n-propyl) of quinoxaline-7- carboxylate 1,4-di-N-oxide in in vitro and in vivo models as antigiardiasis agents.

  Screening four series of esters (methyl, ethyl, isopropyl and n-propyl) of quinoxaline-7- carboxylate 1,4-di-N-oxide in in vitro and in vivo models as antigiardiasis agents.

  Briefly, 4 × 104 trophozoites of G. lamblia were incubated for 48 h at 37 °C with different concentrations of esters of quinoxaline-7-carboxylate 1,4-di-N-oxide, albendazole, metronidazole and nitazoxanide. Afterwards, trophozoites were counted and the half maximal inhibitory concentration (IC50) was calculated by Probit analysis. The in vivo antigiardial activity of the compounds was demonstrated using experimental infections of G. lamblia in suckling female CD-1 mice.

  Compound T-069 with a thienyl, a trifluoromethyl and an isopropyl group at R1-, R2- and R3-position, respectively, on the quinoxaline 1,4-di-N-oxide ring in an in vitro model showed an IC50 value of 0.0014 µM, and 3502 and 1108 times more giardicidal activity than nitazoxanide and metronidazole in an in vivo model.

  Isopropyl ester of quinoxaline-7-carboxylate 1,4-di-N-oxide derivatives showed better giardicidal activity than the reference drugs; therefore, these compounds are good candidates to develop new pharmacological treatment for giardiasis.

  背景：贾第虫病是一个重要的公共卫生问题。然而，其药物治疗主要局限于两种药物，甲硝唑和硝唑酮。目标：在体外和体内模型中筛选四系列喹诺酮-7-羧酸二-N-氧化物（甲基、乙基、异丙基和正丙基）的酯类化合物作为抗贾第虫药剂。 目标：在体外和体内模型中筛选四系列喹诺酮-7-羧酸二-N-氧化物（甲基、乙基、异丙基和正丙基）的酯类化合物作为抗贾第虫药剂。 方法：简而言之，将4 × 104个贾第虫滋养体与不同浓度的喹诺酮-7-羧酸二-N-氧化物酯类、阿苯达唑、甲硝唑和硝唑酮一起在37°C下孵育48小时。然后，对滋养体进行计数，并通过Probit分析计算半最大抑制浓度（IC50）。这些化合物的体内抗贾第虫活性是通过在哺乳期雌性CD-1小鼠中进行贾第虫实验性感染来证明的。 结果：在体外模型中，具有噻吩基、三氟甲基和异丙基基团分别位于喹诺酮-7-羧酸二-N-氧化物环的R1、R2和R3位置的化合物T-069显示出IC50值为0.0014微米，在体内模型中的贾第杀灭活性比硝唑酮和甲硝唑分别高出3502倍和1108倍。 结论：喹诺酮-7-羧酸二-N-氧化物的异丙基酯衍生物显示出比参考药物更好的贾第杀灭活性；因此，这些化合物是开发新的贾第虫病药物治疗的良好候选。
• Synthesis and in vitro evaluation of new ethyl and methyl quinoxaline-7-carboxylate 1,4-di-N-oxide against Entamoeba histolytica
  作者：Blanca Estela Duque-Montaño、Lilia Citlalli Gómez-Caro、Mario Sanchez-Sanchez、Antonio Monge、Efrén Hernández-Baltazar、Gildardo Rivera、Oscar Torres-Angeles

  DOI：10.1016/j.bmc.2013.05.036

  日期：2013.8

  In our search for new antiamoebic agents, a new series of ethyl and methyl quinoxaline-7-carboxylate 1,4-di-N-oxide derivatives have been synthesized using the Beirut reaction. All compounds were characterized by spectroscopic techniques and elemental analysis. Antiamoebic activity was evaluated in vitro against Entamoeba histolytica strain HM1:IMSS by the microdilution method, and the structure-activity relationship was analyzed. We found that eleven quinoxaline derivatives showed greater activity than metronidazole and nitazoxanide with IC50 values in the range 1.99-0.35 mu M. Compounds T-001 and T-016 shows IC50 values of 1.41 and 1.47 mu M, respectively, with a value of selectivity index >60. (C) 2013 Elsevier Ltd. All rights reserved.