2-[[2-(benzyloxycarbonylamino)-3-phenyl-propanoyl]amino]-5-oxo-6-(1,3,4,5-tetramethylimidazol-1-ium-2-yl)sulfanyl-hexanoic acid bromide | 815619-73-9

• 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-(1,3,4,5-tetramethylimidazol-1-ium-2-yl)sulfanyl-hexanoic acid bromide
• 英文别名: (2S)-5-oxo-2-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]-6-(1,3,4,5-tetramethylimidazol-1-ium-2-yl)sulfanylhexanoic acid;bromide
• CAS: 815619-73-9
• 化学式: Br*C₃₀H₃₇N₄O₆S
• 分子量: 661.617
• InChiKey: VPPWLGZCJWTMGW-CCQIZPNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.02
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  (2S)-6-bromo-5-oxo-2-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]hexanoic acid 、 1,3,4,5-tetramethyl-2,3-dihydro-1H-imidazol-2-thione 以 甲醇 为溶剂， 反应 48.0h， 以88%的产率得到2-[[2-(benzyloxycarbonylamino)-3-phenyl-propanoyl]amino]-5-oxo-6-(1,3,4,5-tetramethylimidazol-1-ium-2-yl)sulfanyl-hexanoic acid bromide
  参考文献：
  名称：

  Synthesis of potent water-soluble tissue transglutaminase inhibitors

  摘要：

  Dipeptide-based sulfonium peptidylmethylketones derived from 6-diazo-5-oxo-L-norleucine (DON) have been investigated as potential water-soluble inhibitors of extracellular transglutaminase. The lead compounds were prepared in four steps and exhibited potent activity against tissue transglutaminase. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.006

文献信息

• Synthesis of potent water-soluble tissue transglutaminase inhibitors
  作者：Martin Griffin、Alexandre Mongeot、Russell Collighan、Robert E. Saint、Richard A. Jones、Ian G.C. Coutts、Daniel L. Rathbone

  DOI：10.1016/j.bmcl.2008.09.006

  日期：2008.10

  Dipeptide-based sulfonium peptidylmethylketones derived from 6-diazo-5-oxo-L-norleucine (DON) have been investigated as potential water-soluble inhibitors of extracellular transglutaminase. The lead compounds were prepared in four steps and exhibited potent activity against tissue transglutaminase. (c) 2008 Elsevier Ltd. All rights reserved.
• 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.