thionicotine | 74804-98-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: thionicotine
• 英文别名: (5S)-1-methyl-5-pyridin-3-ylpyrrolidine-2-thione
• CAS: 74804-98-1
• 化学式: C₁₀H₁₂N₂S
• 分子量: 192.285
• InChiKey: WBFMNXBKAMVGAB-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  48.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  thionicotine 、 胆酸 以 甲醇 为溶剂， 反应 12.0h， 以74%的产率得到
  参考文献：
  名称：

  Synthesis and haemolytic activity of novel salts made of nicotine alkaloids and bile acids

  摘要：

  A series of novel salts made of nicotine alkaloids and bile acids were synthesized and their haemolytic activity was examined in vitro using human erythrocytes. All compounds were characterized by spectroscopic methods. The novel salts show membrane-perturbing properties inducing the erythrocyte shape alterations and haemolysis in dose-dependent manner. Nicotine decreases the membrane interacting potential of bile acids in the novel compounds. The presence of sulfur or selenium atom in the nicotine molecule affects the haemolytic activity of its novel salts depending on the hydrophobicity of bile acids. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.005
• 作为产物：
  描述：

  吡啶吡咯酮 在 劳森试剂 作用下， 生成 thionicotine
  参考文献：
  名称：

  Synthesis and haemolytic activity of novel salts made of nicotine alkaloids and bile acids

  摘要：

  A series of novel salts made of nicotine alkaloids and bile acids were synthesized and their haemolytic activity was examined in vitro using human erythrocytes. All compounds were characterized by spectroscopic methods. The novel salts show membrane-perturbing properties inducing the erythrocyte shape alterations and haemolysis in dose-dependent manner. Nicotine decreases the membrane interacting potential of bile acids in the novel compounds. The presence of sulfur or selenium atom in the nicotine molecule affects the haemolytic activity of its novel salts depending on the hydrophobicity of bile acids. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.005

文献信息

• Thioanalogues of N-1-methylanabasine and nicotine – Synthesis and structure
  作者：Marzena Wojciechowska-Nowak、Władysław Boczoń、Beata Warżajtis、Urszula Rychlewska、Beata Jasiewicz

  DOI：10.1016/j.molstruc.2011.01.003

  日期：2011.3

  The synthesis, spectral characteristics and structures of N-1-methyl-6-(pyridin-3-yl)piperidine-2-thione (1) (thioanalogue of N-1-methylanabasine) and N-1-methyl-(5-pyridin-3-yl)pyrrolidine-2-thione (2) (thioanalogue of nicotine) are reported. Both compounds were obtained using Lawesson's reagent. The structures of compounds 1 and 2 are confirmed by NMR, IR, UV and mass spectroscopy, as well as, by X-ray diffraction analysis. Pyridine ring of compound 1 adopts a pseudo-axial orientation in solution, as well as in a solid state. A substantial lengthening of the C=S bond in the crystals of 1 is interpreted as a sign of an enhanced electron delocalization within the thiolactam group due to the presence of several C-H groups in the nearest vicinity of the sulfur atom. In the crystals of 2, which differ from 1 in that the relatively puckered piperidine-2-thione moiety is replaced by the flat pyrrolidine-2-thione ring, no short CH center dot center dot center dot S(=C) contacts are observed. Instead, the packing is governed by stacking interactions between pyridine rings. The pyrrolidine and pyridine rings in 2 are nearly perpendicular to each other and the pyrrolidine moiety adopts a flattened half-chair conformation. (c) 2011 Elsevier B.V. All rights reserved.
• Synthesis and haemolytic activity of novel salts made of nicotine alkaloids and bile acids
  作者：Beata Jasiewicz、Lucyna Mrówczyńska、Karolina Malczewska-Jaskóła

  DOI：10.1016/j.bmcl.2014.01.005

  日期：2014.2

  A series of novel salts made of nicotine alkaloids and bile acids were synthesized and their haemolytic activity was examined in vitro using human erythrocytes. All compounds were characterized by spectroscopic methods. The novel salts show membrane-perturbing properties inducing the erythrocyte shape alterations and haemolysis in dose-dependent manner. Nicotine decreases the membrane interacting potential of bile acids in the novel compounds. The presence of sulfur or selenium atom in the nicotine molecule affects the haemolytic activity of its novel salts depending on the hydrophobicity of bile acids. (C) 2014 Elsevier Ltd. All rights reserved.