N-(2-aminoethyl)-2-nitro-N-phenylmethoxybenzenesulfonamide | 1048037-21-3

• 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: N-(2-aminoethyl)-2-nitro-N-phenylmethoxybenzenesulfonamide
• CAS: 1048037-21-3
• 化学式: C₁₅H₁₇N₃O₅S
• 分子量: 351.383
• InChiKey: SAUWVXNERCAUKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(2-aminoethyl)-2-nitro-N-phenylmethoxybenzenesulfonamide 、 bis(4-isothiocyanatophenyl)amine 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Efficient one-pot synthesis of 1-alkoxy-2-arylaminoimidazolines from N-alkoxy-N-(2-aminoethyl)-2-nitrobenzenesulfonamides and arylisothiocyanates

  摘要：

  A new synthetic approach towards 1-alkoxy-2-aminoimidazolines that uses N-alkoxy-N-(2-aminoethyl)2-n itrobenzenes ulfonam ides as nucleophile reagents for the reaction with isothiocyanates is reported. Hence, the synthesis of 1-alkoxy-2-aminoimidazolines was performed in high yield with a one-pot procedure involving thiourea formation, nosyl group removal and spontaneous cyclization (42-77% overall yield). (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.098
• 作为产物：
  描述：

  N-(benzyloxy)-N-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-2-nitrobenzenesulfonamide 在 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 0.33h， 以76%的产率得到N-(2-aminoethyl)-2-nitro-N-phenylmethoxybenzenesulfonamide
  参考文献：
  名称：

  Efficient one-pot synthesis of 1-alkoxy-2-arylaminoimidazolines from N-alkoxy-N-(2-aminoethyl)-2-nitrobenzenesulfonamides and arylisothiocyanates

  摘要：

  A new synthetic approach towards 1-alkoxy-2-aminoimidazolines that uses N-alkoxy-N-(2-aminoethyl)2-n itrobenzenes ulfonam ides as nucleophile reagents for the reaction with isothiocyanates is reported. Hence, the synthesis of 1-alkoxy-2-aminoimidazolines was performed in high yield with a one-pot procedure involving thiourea formation, nosyl group removal and spontaneous cyclization (42-77% overall yield). (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.098

文献信息

• A New Nonpolar <i>N</i> -Hydroxy Imidazoline Lead Compound with Improved Activity in a Murine Model of Late-Stage Trypanosoma brucei brucei Infection Is Not Cross-Resistant with Diamidines
  作者：Carlos H. Ríos Martínez、Florence Miller、Kayathiri Ganeshamoorthy、Fabienne Glacial、Marcel Kaiser、Harry P. de Koning、Anthonius A. Eze、Laura Lagartera、Tomás Herraiz、Christophe Dardonville

  DOI：10.1128/aac.03958-14

  日期：2015.2

  slightly improve survival. In addition, 14d showed weak activity in the chronic model of central nervous system infection in mice. No evidence of reduction of this compound with hepatic microsomes and mitochondria was found in vitro, suggesting that N-hydroxy imidazolines are metabolically stable and have intrinsic activity against T. brucei. In contrast to its unsubstituted parent compound, the uptake

  晚期昏睡病的治疗需要能够穿过血脑屏障（BBB）到达大脑中寄生虫的药物。我们在这里报告了比西咪唑啉的四种新的N-羟基和12种新的N-烷氧基衍生物的合成和评估，它们可作为治疗晚期昏睡病的潜在药物。这些化合物与母体铅相比具有降低的碱性（即，在生理pH下离子化程度较低），并在体外针对第一阶段和第二阶段昏睡病的鼠模型对布鲁氏锥虫进行了体外评估，并在体内进行了评估。还确定了耐药性，理化参数，体外血脑屏障通透性和微粒体稳定性。N-羟基咪唑啉类似物在体内最有效，其中4-（（1-hydroxy-4，5-二氢-1H-咪唑-2-基）氨基）-N-（4-（（1-羟基-4,5-二氢-1H-咪唑-2-基）氨基）苯基）苯甲酰胺（14d）显示100治愈第一阶段疾病的百分率是15％，而15d，16d和17d似乎可以稍微提高生存率。另外，在小鼠中枢神经系统感染的慢性模型中，14d显示出弱的活性。在体外未发现该化合物被肝微粒体和
• Efficient one-pot synthesis of 1-alkoxy-2-arylaminoimidazolines from N-alkoxy-N-(2-aminoethyl)-2-nitrobenzenesulfonamides and arylisothiocyanates
  作者：Ainhoa Mascaraque、Lidia Nieto、Christophe Dardonville

  DOI：10.1016/j.tetlet.2008.05.098

  日期：2008.7

  A new synthetic approach towards 1-alkoxy-2-aminoimidazolines that uses N-alkoxy-N-(2-aminoethyl)2-n itrobenzenes ulfonam ides as nucleophile reagents for the reaction with isothiocyanates is reported. Hence, the synthesis of 1-alkoxy-2-aminoimidazolines was performed in high yield with a one-pot procedure involving thiourea formation, nosyl group removal and spontaneous cyclization (42-77% overall yield). (c) 2008 Elsevier Ltd. All rights reserved.