{2-[(4-chloro-2-nitrophenyl)thio]phenyl}hydrazine | 68207-44-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: {2-[(4-chloro-2-nitrophenyl)thio]phenyl}hydrazine
• 英文别名: 2-Nitro-4-chloro-2'-hydrazinodiphenylsulfid；[2-(4-Chloro-2-nitrophenyl)sulfanylphenyl]hydrazine
• CAS: 68207-44-3
• 化学式: C₁₂H₁₀ClN₃O₂S
• 分子量: 295.749
• InChiKey: KFNUKNZPCUMJMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 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-[(4-chloro-2-nitrophenyl)thio]phenyl}hydrazine 在 氢氧化钾 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 6.25h， 生成 2-Chloro-5,6-dihydro-dibenzo[1,4,5]thiadiazepine
  参考文献：
  名称：

  New method for the synthesis of chloro-substituted dibenzo[b,f][1,4,5]thiadiazepines and their 5,6-dihydro derivatives

  摘要：

  DOI：

  10.1021/jo00132a054
• 作为产物：
  描述：

  2,5-二氯硝基苯 在 盐酸 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 生成 {2-[(4-chloro-2-nitrophenyl)thio]phenyl}hydrazine
  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

• Dibenzo[ <i>b</i> , <i>f</i> ][1,4,5]chalcogenadiazepine Photoswitches: Conversion of Excitation Energy into Ring Strain
  作者：Xin Shen、Cefei Zhang、Fengying Lan、Zhishan Su、Yuanqin Zheng、Tingting Zheng、Qin Xiong、Xinyu Xie、Guangxi Du、Xiaohu Zhao、Changwei Hu、Pengchi Deng、Zhipeng Yu

  DOI：10.1002/anie.202209441

  日期：2022.10.10

  Chalcogen-bridged seven-membered cyclic azobenzenes, dibenzo[b,f][1,4,5]chalcogenadiazepine (DBChD), exhibit distinct photo-switching characters with a high-energy E-configuration, especially for sulfur-bridged DBTD with an energy transduction efficiency of 21 % (η) under 445 nm laser activation. Introducing oligothiophene π-EDG on DBTD could further elevate the absorption λmax and coefficient ϵ, reaching

  硫属元素桥接的七元环状偶氮苯二苯并[ b , f ][1,4,5]硫属二氮杂卓 (DBChD) 具有高能 E 构型的独特光开关特性，特别是对于具有高能 E 构型的硫桥接 DBTD在 445 nm 激光激活下，能量转换效率为 21% (η)。在 DBTD 上引入低聚噻吩 π-EDG 可以进一步提高吸收 λ max和系数 ϵ，达到 η=29 %。
• 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.
• 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