1,4,5-trimethyl-3-phenyl-1H-imidazole-2(3H)-thione | 1449280-35-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,4,5-trimethyl-3-phenyl-1H-imidazole-2(3H)-thione
• 英文别名: 1,4,5-Trimethyl-3-phenylimidazole-2-thione
• CAS: 1449280-35-6
• 化学式: C₁₂H₁₄N₂S
• 分子量: 218.323
• InChiKey: GKCFUPQNPMTFOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2S)-6-bromo-5-oxo-2-[[2-(phenylmethoxycarbonylamino)acetyl]amino]hexanoic acid 、 1,4,5-trimethyl-3-phenyl-1H-imidazole-2(3H)-thione 以 甲醇 为溶剂， 反应 48.0h， 以78%的产率得到2-[[2-(benzyloxycarbonylamino)acetyl]amino]-5-oxo-6-(1,4,5-trimethyl-3-phenyl-imidazol-1-ium-2-yl)sulfanyl-hexanoic acid bromide
  参考文献：
  名称：

  Imidazolium-based warheads strongly influence activity of water-soluble peptidic transglutaminase inhibitors

  摘要：

  New peptidic water-soluble inhibitors are reported. In addition to the carboxylate moiety, a new polar warhead was explored. Depending on the size of its substituents, the newly appended imidazolium scaffold designed to enhance the hydrophilic character of the inhibitors could induce a good inhibition for tissue transglutaminase (TG2) and blood coagulation factor XIIIa (EXIIIa). Correlated with the narrow tunnel that hosts the target catalytic cysteine residue, the various modulations suggest a bent conformation of the ligands as the binding pattern mode. Analogues in the dialkylsulfonium series were also tested and showed specificity for TG2 over FXIIIa. (c) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.018
• 作为产物：
  描述：

  3-羟基-2-丁酮 、 1-甲基-3-苯基硫脲 以 正己醇 为溶剂， 以59%的产率得到1,4,5-trimethyl-3-phenyl-1H-imidazole-2(3H)-thione
  参考文献：
  名称：

  Imidazolium-based warheads strongly influence activity of water-soluble peptidic transglutaminase inhibitors

  摘要：

  New peptidic water-soluble inhibitors are reported. In addition to the carboxylate moiety, a new polar warhead was explored. Depending on the size of its substituents, the newly appended imidazolium scaffold designed to enhance the hydrophilic character of the inhibitors could induce a good inhibition for tissue transglutaminase (TG2) and blood coagulation factor XIIIa (EXIIIa). Correlated with the narrow tunnel that hosts the target catalytic cysteine residue, the various modulations suggest a bent conformation of the ligands as the binding pattern mode. Analogues in the dialkylsulfonium series were also tested and showed specificity for TG2 over FXIIIa. (c) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.018