2-氯-5-硝基苯硫醇 | 89880-53-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氯-5-硝基苯硫醇
• 英文名称: 2-chloro-5-nitrobenzenethiol
• 英文别名: 5-amino-2-chlorothiophenol；2-chloro-5-nitro-benzenethiol
• CAS: 89880-53-5
• 化学式: C₆H₄ClNO₂S
• 分子量: 189.622
• InChiKey: NBFJQCOMMJXWHD-UHFFFAOYSA-N

物化性质

• 沸点：
  291.7±25.0 °C(Predicted)
• 密度：
  1.506±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氯-5-硝基苯硫醇 在 碳酸氢钠 作用下， 以 氘代二甲亚砜 为溶剂， 以88%的产率得到4-chloro-3-((5-amino-2-chlorophenyl)disulfanyl)aniline
  参考文献：
  名称：

  Synthesis and evaluation of N-(methylthiophenyl)picolinamide derivatives as PET radioligands for metabotropic glutamate receptor subtype 4

  摘要：

  In recent years, mGlu(4) has received great research attention because of the potential benefits of mGlu(4) activation in treating numerous brain disorders, such as Parkinson's disease (PD). A specific mGlu(4) PET radioligand could be an important tool in understanding the role of mGlu(4) in both healthy and disease conditions, and also for the development of new drugs. In this study, we synthesized four new N-(methylthiophenyl)picolinamide derivatives 11-14. Of these ligands, 11 and 14 showed high in vitro binding affinity for mGlu(4) with IC50 values of 3.4 nM and 3.1 nM, respectively, and suitable physicochemical parameters. Compound 11 also showed enhanced metabolic stability and good selectivity to other mGluRs. [C-11]11 and [C-11]14 were radiolabeled using the [C-11] methylation of the thiophenol precursors 20a and 20c with [C-11]CH3I in 19.0% and 34.8% radiochemical yields (RCY), and their specific activities at the end of synthesis (EOS) were 496 +/- 138 GBq/mu mol (n = 6) and 463 +/- 263 GBq/mu mol (n = 4), respectively. The PET studies showed that [C-11]11 accumulated fast into the brain and had higher uptake, slower washout and 25% better contrast than [C-11]2, indicating improved imaging characteristics as PET radiotracer for mGlu(4) compared to [C-11]2. Therefore, [C-11]11 will be a useful radioligand to investigate mGlu(4) in different biological applications. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.015
• 作为产物：
  描述：

  (2-氯-5-硝基苯基)硫氰酸盐 在 sodium tetrahydroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.07h， 以80%的产率得到2-氯-5-硝基苯硫醇
  参考文献：
  名称：

  Still, Ian W. J.; Sayeed, Vilayat A., Synthetic Communications, 1983, vol. 13, # 14, p. 1181 - 1192

  摘要：

  DOI：

文献信息

• Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function
  申请人：——

  公开号：US20040077605A1

  公开（公告）日：2004-04-22

  Fused cyclic compounds, methods of using such compounds in the treatment of nuclear hormone receptor-associated conditions such as cancer and immune disorders, and pharmaceutical compositions containing such compounds.

  融合的环化合物，使用这种化合物治疗与核激素受体相关的疾病，如癌症和免疫紊乱的方法，以及含有这种化合物的药物组合物。
• METHOD FOR THE PREPARATION OF FUSED HETEROCYCLIC SUCCINIMIDE COMPOUNDS AND ANALOGS THEREOF
  申请人：Salvati E. Mark

  公开号：US20050119228A1

  公开（公告）日：2005-06-02

  Fused cyclic compounds, methods of using such compounds in the treatment of nuclear hormone receptor-associated conditions such as cancer and immune disorders, and pharmaceutical compositions containing such compounds.

  融合的环化合物，使用这种化合物治疗与核激素受体相关的疾病，如癌症和免疫紊乱的方法，以及含有这种化合物的药物组合物。
• Improved synthesis of the thiophenol precursor N-(4-chloro-3-mercaptophenyl)picolinamide for making the mGluR4 PET ligands
  作者：Junfeng Wang、Timothy M. Shoup、Anna-Liisa Brownell、Zhaoda Zhang

  DOI：10.1016/j.tet.2019.06.010

  日期：2019.7

  However, the previously reported multi-step synthesis of the thiophenol precursor suffered from low yields and difficult workup procedures. To support the translational research of [11C]mG4P012 and the other potential applications, we have developed a new route for synthesis of the thiophenol precursor and optimized the reaction conditions. The synthesis of N-(4-chloro-3-mercaptophenyl)picolinamide

  最近，[ 11 C] mG4P012（以前是[ 11 C] KALB012，现在被Prexton Therapeutics命名为[ 11 C] PXT012253）在潜在治疗药物PXT0002331（mGluR4 PAM）的临床前开发中被用作生物标志物。 PD和1-多巴引起的运动障碍。[ 11 C] mG4P012被证明是猴脑中mGluR4以及人类受试者进一步发展的有前途的PET放射性配体。然而，先前报道的硫酚前体的多步合成遭受产率低和后处理程序困难的困扰。支持[ 11C] mG4P012和其他潜在的应用，我们已经开发出了一种新的合成苯硫酚前体的途径，并优化了反应条件。由1-氯-4-硝基苯合成N-（4-氯-3-巯基苯基）吡啶甲酸酰胺的总收率从8％提高到52％，并且易于处理且克级。
• [EN] MODULATORS OF METABOTROPIC GLUTAMATE RECEPTOR 4<br/>[FR] MODULATEURS DU RÉCEPTEUR DU GLUTAMATE MÉTABOTROPIQUE 4
  申请人：MASSACHUSETTS GEN HOSPITAL

  公开号：WO2020146515A1

  公开（公告）日：2020-07-16

  The present application provides picolinamide compounds that can be used as allosteric positron emission tomography ("PET") imaging probes. Methods of using these compounds for treating a neurodegenerative disease are also provided.

  本申请提供了可以用作变构位置发射断层扫描（PET）成像探针的吡啶甲酰胺化合物。同时还提供了利用这些化合物治疗神经退行性疾病的方法。
• [EN] FUSED HETEROCYCLIC SUCCINIMIDE COMPOUNDS AND ANALOGS THEREOF, MODULATORS OF NUCLEAR HORMONE RECEPTOR FUNCTION<br/>[FR] COMPOSES DE SUCCINIMIDE HETEROCYCLIQUES FUSIONNES ET LEURS ANALOGUES, MODULATEURS DE LA FONCTION DE RECEPTEUR HORMONAL NUCLEAIRE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2002024702A1

  公开（公告）日：2002-03-28

  Fused cyclic compounds, methods of using such compounds in the treatment of nuclear hormone receptor-associated conditions such as cancer and immune disorders, and pharmaceutical compositions containing such compounds.

  融合环化合物，使用这种化合物治疗与核激素受体相关的疾病，如癌症和免疫紊乱的方法，以及包含这种化合物的药物组合物。