[2-(2-硝基苯基)硫烷基苯基]肼 | 68207-43-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: [2-(2-硝基苯基)硫烷基苯基]肼
• 英文名称: {2-[(2-nitrophenyl)thio]phenyl}hydrazine
• 英文别名: 2-Nitro-2'-hydrazinodiphenylsulfid；{2-[(2-Nitrophenyl)sulfanyl]phenyl}hydrazine；[2-(2-nitrophenyl)sulfanylphenyl]hydrazine
• CAS: 68207-43-2
• 化学式: C₁₂H₁₁N₃O₂S
• 分子量: 261.304
• InChiKey: IPNFDKWWGMTGPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [2-(2-硝基苯基)硫烷基苯基]肼 、 3-(4-苯基-哌嗪-1-基)-丙酸 在 potassium carbonate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.0h， 生成 3-(4-methylpiperazin-1-yl)-N-(10H-phenothiazin-10-yl)propanamide
  参考文献：
  名称：

  N-Acylaminophenothiazines: Neuroprotective agents displaying multifunctional activities for a potential treatment of Alzheimer’s disease

  摘要：

  We have previously reported the multifunctional profile of N-(3-chloro-10H-phenothiazin-10-yl)-3-(dimethylamino)propanamide (1) as an effective neuroprotectant and selective butyrylcholinesterase inhibitor. In this paper, we have developed a series of N-acylaminophenothiazines obtained from our compound library or newly synthesised. At micro- and sub-micromolar concentrations, these compounds selectively inhibited butyrylcholinesterase (BuChE), protected neurons against damage caused by both exogenous and mitochondrial free radicals, showed low toxicity, and could penetrate into the CNS. In addition, N-(3-chloro-10H-phenothiazin-10-yl)-2-(pyrrolidin-1-yl)acetamide (11) modulated the cytosolic calcium concentration and protected human neuroblastoma cells against several toxics, such as calcium overload induced by an L-type Ca2+-channel agonist, tau-hyperphosphorylation induced by okadaic acid and A beta peptide. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.003
• 作为产物：
  描述：

  2-氨基-2'-硝基二苯硫醚 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 3.0h， 以57%的产率得到[2-(2-硝基苯基)硫烷基苯基]肼
  参考文献：
  名称：

  N-Acylaminophenothiazines: Neuroprotective agents displaying multifunctional activities for a potential treatment of Alzheimer’s disease

  摘要：

  We have previously reported the multifunctional profile of N-(3-chloro-10H-phenothiazin-10-yl)-3-(dimethylamino)propanamide (1) as an effective neuroprotectant and selective butyrylcholinesterase inhibitor. In this paper, we have developed a series of N-acylaminophenothiazines obtained from our compound library or newly synthesised. At micro- and sub-micromolar concentrations, these compounds selectively inhibited butyrylcholinesterase (BuChE), protected neurons against damage caused by both exogenous and mitochondrial free radicals, showed low toxicity, and could penetrate into the CNS. In addition, N-(3-chloro-10H-phenothiazin-10-yl)-2-(pyrrolidin-1-yl)acetamide (11) modulated the cytosolic calcium concentration and protected human neuroblastoma cells against several toxics, such as calcium overload induced by an L-type Ca2+-channel agonist, tau-hyperphosphorylation induced by okadaic acid and A beta peptide. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.003

文献信息

• New method for the synthesis of chloro-substituted dibenzo[b,f][1,4,5]thiadiazepines and their 5,6-dihydro derivatives
  作者：Carlos Corral、Jaime Lissavetzky、Gloria Quintanilla

  DOI：10.1021/jo00132a054

  日期：1982.5
• CORRAL, C.;LISSAVETZKY, J.;QUINTANILLA, G., J. ORG. CHEM., 1982, 47, N 11, 2214-2215
  作者：CORRAL, C.、LISSAVETZKY, J.、QUINTANILLA, G.

  DOI：——

  日期：——
• CORRAL C.; LISSAVETZKY J.; QUINTANILLA G., J. HETEROCYCL. CHEM., 1978, 15, NO 7, 1137-1140
  作者：CORRAL C.、 LISSAVETZKY J.、 QUINTANILLA G.

  DOI：——

  日期：——
• N-Acylaminophenothiazines: Neuroprotective agents displaying multifunctional activities for a potential treatment of Alzheimer’s disease
  作者：Gema C. González-Muñoz、Mariana P. Arce、Beatriz López、Concepción Pérez、Alejandro Romero、Laura del Barrio、María Dolores Martín-de-Saavedra、Javier Egea、Rafael León、Mercedes Villarroya、Manuela G. López、Antonio G. García、Santiago Conde、María Isabel Rodríguez-Franco

  DOI：10.1016/j.ejmech.2011.03.003

  日期：2011.6

  We have previously reported the multifunctional profile of N-(3-chloro-10H-phenothiazin-10-yl)-3-(dimethylamino)propanamide (1) as an effective neuroprotectant and selective butyrylcholinesterase inhibitor. In this paper, we have developed a series of N-acylaminophenothiazines obtained from our compound library or newly synthesised. At micro- and sub-micromolar concentrations, these compounds selectively inhibited butyrylcholinesterase (BuChE), protected neurons against damage caused by both exogenous and mitochondrial free radicals, showed low toxicity, and could penetrate into the CNS. In addition, N-(3-chloro-10H-phenothiazin-10-yl)-2-(pyrrolidin-1-yl)acetamide (11) modulated the cytosolic calcium concentration and protected human neuroblastoma cells against several toxics, such as calcium overload induced by an L-type Ca2+-channel agonist, tau-hyperphosphorylation induced by okadaic acid and A beta peptide. (C) 2011 Elsevier Masson SAS. All rights reserved.