N-(4-(methylthio)phenyl)picolinamide

• 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-(4-(methylthio)phenyl)picolinamide
• 英文别名: N-(4-methylsulfanylphenyl)pyridine-2-carboxamide
• 化学式: C₁₃H₁₂N₂OS
• 分子量: 244.317
• InChiKey: BBBNEPHODZHGRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  67.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-(methylthio)phenyl)picolinamide 在 二苯甲酮亚胺 、 copper(l) chloride 、 盐酸 作用下， 以 甲苯 、 四氢呋喃 、 水 为溶剂， 反应 16.0h， 以81%的产率得到N-(2-amino-4-(methylthio)phenyl)picolinamide
  参考文献：
  名称：

  铜介导的苯胺邻位C H 初级胺化

  摘要：

  我们在此报告了通过使用廉价且市售的二苯甲酮亚胺作为胺化试剂对苯胺进行铜介导的邻位C H 初级胺化。该协议显示出良好的官能团耐受性和杂环兼容性。药物的后期多样化证明了该协议的综合效用。

  DOI：

  10.1016/j.tetlet.2021.153099
• 作为产物：
  描述：

  2-吡啶甲酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(4-(methylthio)phenyl)picolinamide
  参考文献：
  名称：

  芳烃与仲胺的铜催化电化学 C-H 胺化

  摘要：

  电化学氧化是对需要腐蚀性化学计量化学氧化剂的传统方法的一种环保解决方案。然而，迄今为止，结合过渡金属催化和电化学技术的 CH 官能化主要限于使用贵金属和分离的电池。在此，我们报告了使用未分割的电化学电池在室温下铜催化芳烃电化学 CH 胺化的第一个例子，从而为芳胺的构建提供了实用的解决方案。使用 n-Bu4NI 作为氧化还原介质对于这种转变至关重要。基于包括动力学曲线、同位素效应、循环伏安分析和自由基抑制实验在内的机理研究，该反应似乎是通过单电子转移 (SET) 过程进行的，并且可能涉及高价 Cu(III) 物质。这些发现为使用氧化还原介质的过渡金属催化电化学 CH 官能化反应提供了新途径。

  DOI：

  10.1021/jacs.8b07380

文献信息

• [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。
• Synthesis and evaluation of N-(methylthiophenyl)picolinamide derivatives as PET radioligands for metabotropic glutamate receptor subtype 4
  作者：Kun-Eek Kil、Pekka Poutiainen、Zhaoda Zhang、Aijun Zhu、Darshini Kuruppu、Shilpa Prabhakar、Ji-Kyung Choi、Bakhos A. Tannous、Anna-Liisa Brownell

  DOI：10.1016/j.bmcl.2015.11.015

  日期：2016.1

  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.
• INHIBITORS OF THE RAS ONCOPROTEIN, METHODS OF MAKING AND METHODS OF USE THEREOF
  申请人：University of Louisville Research Foundation, Inc.

  公开号：US20210137939A1

  公开（公告）日：2021-05-13

  A compound for use in treating a disease associated with activating mutations in RAS, or for use in treating a disease treatable by a reduction in RAS activity, is selected from a compound of Formula (I), salts and esters thereof. The compounds are particularly useful in treating cancer.
• MODULATORS OF METABOTROPIC GLUTAMATE RECEPTOR 4
  申请人：The General Hospital Corporation

  公开号：US20220118117A1

  公开（公告）日：2022-04-21

  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.