2-(((3-phenylsulfonylfuroxan-4-yl)oxy)ethyl)ethylamine | 1300743-25-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(((3-phenylsulfonylfuroxan-4-yl)oxy)ethyl)ethylamine
• 英文别名: 2-[[4-(benzenesulfonyl)-5-oxido-1,2,5-oxadiazol-5-ium-3-yl]oxy]-N-ethylethanamine
• CAS: 1300743-25-2
• 化学式: C₁₂H₁₅N₃O₅S
• 分子量: 313.334
• InChiKey: LIPCVKOKNFUFNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(9-(2-(chlorocarbonyl)phenyl)-6-(diethylamino)-3H-xanthen-3-ylidene)-N-ethylethanaminium chloride 、 2-(((3-phenylsulfonylfuroxan-4-yl)oxy)ethyl)ethylamine 在 三乙胺 作用下， 反应 24.0h， 以27%的产率得到4-(2-(2-(6-(diethylamino)-3-(diethyliminio)-3H-xanthen-9-yl)-N-ethylbenzamido)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide
  参考文献：
  名称：

  Tuning NO release of organelle-targeted furoxan derivatives and their cytotoxicity against lung cancer cells

  摘要：

  DOI：

  10.1016/j.bioorg.2021.104911
• 作为产物：
  描述：

  呋咱氮氧化物供体 、 N-乙基乙醇胺 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以48%的产率得到2-(((3-phenylsulfonylfuroxan-4-yl)oxy)ethyl)ethylamine
  参考文献：
  名称：

  Amodiaquine analogues containing NO-donor substructures: Synthesis and their preliminary evaluation as potential tools in the treatment of cerebral malaria

  摘要：

  The synthesis and physico-chemical properties of novel compounds obtained by conjugation of amodiaquine with moieties containing either furoxan or nitrooxy NO-donor substructures are described. The synthesised compounds were tested in vitro against both the chloroquine sensitive, 010 and the chloroquine resistant, W-2 strains of Plasmodium falciparum (P falciparum). Most of the compounds showed an antiplasmodial activity comparable to that of the parent drug. By comparing the activities of simple related structures devoid of the ability to release NO, it appears that the contribution of NO to the antiplasmodial action in vitro is marginal. All the compounds were able to relax rat aorta strips with a NO-dependent mechanism, thus showing their capacity to release NO in the vessels. A preliminary in vivo study using Plasmodium berghei ANKA-infected mice showed a trend for prolonged survival of mice with cerebral malaria treated with compound 40, which is potent and fast amodiaquine-derived NO-donor, when compared with amodiaquine alone or with compound 31, a milder NO-donor. The two compounds showed in vivo antiplasmodial activity similar to that of amodiaquine. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.029

文献信息

• Amodiaquine analogues containing NO-donor substructures: Synthesis and their preliminary evaluation as potential tools in the treatment of cerebral malaria
  作者：Massimo Bertinaria、Stefano Guglielmo、Barbara Rolando、Marta Giorgis、Cristina Aragno、Roberta Fruttero、Alberto Gasco、Silvia Parapini、Donatella Taramelli、Yuri C. Martins、Leonardo J.M. Carvalho

  DOI：10.1016/j.ejmech.2011.02.029

  日期：2011.5

  The synthesis and physico-chemical properties of novel compounds obtained by conjugation of amodiaquine with moieties containing either furoxan or nitrooxy NO-donor substructures are described. The synthesised compounds were tested in vitro against both the chloroquine sensitive, 010 and the chloroquine resistant, W-2 strains of Plasmodium falciparum (P falciparum). Most of the compounds showed an antiplasmodial activity comparable to that of the parent drug. By comparing the activities of simple related structures devoid of the ability to release NO, it appears that the contribution of NO to the antiplasmodial action in vitro is marginal. All the compounds were able to relax rat aorta strips with a NO-dependent mechanism, thus showing their capacity to release NO in the vessels. A preliminary in vivo study using Plasmodium berghei ANKA-infected mice showed a trend for prolonged survival of mice with cerebral malaria treated with compound 40, which is potent and fast amodiaquine-derived NO-donor, when compared with amodiaquine alone or with compound 31, a milder NO-donor. The two compounds showed in vivo antiplasmodial activity similar to that of amodiaquine. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Tuning NO release of organelle-targeted furoxan derivatives and their cytotoxicity against lung cancer cells
  作者：Federica Sodano、Elena Gazzano、Barbara Rolando、Elisabetta Marini、Loretta Lazzarato、Roberta Fruttero、Chiara Riganti、Alberto Gasco

  DOI：10.1016/j.bioorg.2021.104911

  日期：2021.6