2-(4-chloro-2-nitrophenylthio)aniline | 14393-61-4

• 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-nitrophenylthio)aniline
• 英文别名: 2-(4-chloro-2-nitro-phenylsulfanyl)-aniline；2-(4-Chlor-2-nitro-phenylmercapto)-anilin；2-Amino-4'-chloro-2'-nitrodiphenylsulphid；2-Amino-4'-chlor-2'-nitro-diphenylsulfid；2-(4-Chloro-2-nitro-phenylsulfanyl)-phenylamine；2-(4-chloro-2-nitrophenyl)sulfanylaniline
• CAS: 14393-61-4
• 化学式: C₁₂H₉ClN₂O₂S
• 分子量: 280.735
• InChiKey: RIQHSWGSXDCMIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-chloro-2-nitrophenylthio)aniline 在 盐酸 、 铁粉 、 sodium nitrite 作用下， 生成 N,N-diethyl-N'-[5-chloro-2-(2-chloro-phenylsulfanyl)-phenyl]-ethylenediamine
  参考文献：
  名称：

  Morisawa et al., Yakugaku Kenkyu, 1957, vol. 29, p. 161

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基苯硫醇 、 2,5-二氯硝基苯 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以60%的产率得到2-(4-chloro-2-nitrophenylthio)aniline
  参考文献：
  名称：

  Modulation of cAMP-Specific PDE without Emetogenic Activity: New Sulfide-Like PDE7 Inhibitors

  摘要：

  A forward chemical genetic approach was followed to discover new targets and lead compounds for Parkinson's disease (PD) treatment. By analysis of the cell protection produced by some small molecules, a diphenyl sulfide compound was revealed to be a new phosphodiesterase 7 (PDE7) inhibitor and identified as a new hit. This result allows us to confirm the utility of PDE7 inhibitors as a potential pharmacological treatment of PD. On the basis of these data, a diverse family of diphenyl sulfides has been developed and pharmacologically evaluated in the present work. Moreover, to gain insight into the safety of PDE7 inhibitors for human chronic treatment, we evaluated the new compounds in a surrogate emesis model, showing nonemetic effects.

  DOI：

  10.1021/jm501090m

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 %。
• Onda et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1956, vol. 76, p. 564
  作者：Onda et al.

  DOI：——

  日期：——
• Chlorinated <i>o</i>-Dimethylaminopropylaminodiphenyl Sulfide Derivatives
  作者：ALFRED. BURGER、JOSEPH L. STANMYER

  DOI：10.1021/jo01118a013

  日期：1956.12.1
• 354. A rearrangement of o-acetamido-sulphoxides
  作者：Alfred Levi、Leonard A. Warren、Samuel Smiles

  DOI：10.1039/jr9330001490

  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.