2-[[2-(benzyloxycarbonylamino)-3-phenyl-propanoyl]amino]-5-oxo-6-(1,4,5-trimethyl-3-propyl-imidazol-1-ium-2-yl)sulfanyl-hexanoic acid bromide | 1449280-40-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[[2-(benzyloxycarbonylamino)-3-phenyl-propanoyl]amino]-5-oxo-6-(1,4,5-trimethyl-3-propyl-imidazol-1-ium-2-yl)sulfanyl-hexanoic acid bromide
• 英文别名: (2S)-5-oxo-2-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]-6-(1,4,5-trimethyl-3-propylimidazol-1-ium-2-yl)sulfanylhexanoic acid;bromide
• CAS: 1449280-40-3
• 化学式: Br*C₃₂H₄₁N₄O₆S
• 分子量: 689.671
• InChiKey: KBJRDBLFDLQYJK-DHBRAOIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  156
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-Methyl-N'-n-propylthioharnstoff 以 甲醇 、 正己醇 为溶剂， 反应 48.0h， 生成 2-[[2-(benzyloxycarbonylamino)-3-phenyl-propanoyl]amino]-5-oxo-6-(1,4,5-trimethyl-3-propyl-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

文献信息

• Imidazolium-based warheads strongly influence activity of water-soluble peptidic transglutaminase inhibitors
  作者：Eduard Badarau、Alexandre Mongeot、Russell Collighan、Dan Rathbone、Martin Griffin

  DOI：10.1016/j.ejmech.2013.05.018

  日期：2013.8

  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.