N-(4-chlorophenyl)-2-(methylthio)nicotinamide | 141841-42-1

• 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-chlorophenyl)-2-(methylthio)nicotinamide
• 英文别名: N-(4-chlorophenyl)-2-methylsulfanylpyridine-3-carboxamide
• CAS: 141841-42-1
• 化学式: C₁₃H₁₁ClN₂OS
• 分子量: 278.762
• InChiKey: ULWMKXPCRRFGQG-UHFFFAOYSA-N

物化性质

• 沸点：
  359.8±37.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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-chlorophenyl)-2-(methylthio)nicotinamide 、 N-methoxypyridinium methylsulfate 在 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate 、 sodium 2,2,2-trifluoroacetate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以32%的产率得到N-(4-chlorophenyl)-2-((pyridin-2-ylmethyl)thio)nicotinamide
  参考文献：
  名称：

  通过光氧化还原和弱 Brønsted 碱催化硫醚的 α-杂芳基化

  摘要：

  我们报告了硫醚对 α-硫代烷基自由基的 C-H 活化以及它们与N-甲氧基杂芳鎓盐的加成，用于氧化还原中性合成 α-杂芳族硫醚。研究与两步活化机制一致，其中通过光氧化还原催化剂将硫醚氧化为硫化物自由基阳离子，然后通过弱 Brønsted 碱催化剂进行 α-C-H 去质子化以提供 α-硫代烷基自由基。此外，N-甲氧基杂芳鎓盐作为甲氧基自由基的来源，有助于α-硫代烷基自由基的产生和再生光氧化还原催化循环的牺牲氧化剂，发挥了额外的作用。

  DOI：

  10.1021/acs.orglett.1c02151
• 作为产物：
  描述：

  2-巯基烟酸 在 氯化亚砜 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 N-(4-chlorophenyl)-2-(methylthio)nicotinamide
  参考文献：
  名称：

  Synthesis and Antifungal Activity of Nicotinamide Derivatives as Succinate Dehydrogenase Inhibitors

  摘要：

  Thirty-eight nicotinamide derivatives were designed and synthesized as potential succinate dehydrogenase inhibitors (SDHI) and precisely characterized by H-1 NMR, ESI-MS, and elemental analysis. The compounds were evaluated against two phytopathogenic fungi, Rhizoctonia solani and Sclerotinia sclerotiorum, by mycelia growth inhibition assay in vitro. Most of the compounds displayed moderate activity, in which, 3a-17 exhibited the most potent antifungal activity against R. solani and S. sclerotiorum with IC50 values of 15.8 and 20.3 mu M, respectively, comparable to those of the commonly used fungicides boscalid and carbendazim. The structure-activity relationship (SAR) of nicotinamide derivatives demonstrated that the meta-position of aniline was a key position contributing to the antifungal activity. Inhibition activities against two fungal SDHs were tested and achieved the same tendency with the data acquired from in vitro antifungal assay. Significantly, 3a-17 was demonstrated to successfully suppress disease development in S. sclerotiorum infected cole in vivo. In the molecular docking simulation, sulfur and chlorine of 3a-17 were bound with PHE291 and PRO150 of the SDH homology model, respectively, which could explain the probable mechanism of action between the inhibitory and target protein.

  DOI：

  10.1021/jf405437k