methyl (S)-2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-6-bromo-5-oxohexanoate | 1092077-67-2

• 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: methyl (S)-2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-6-bromo-5-oxohexanoate
• CAS: 1092077-67-2
• 化学式: C₂₄H₂₇BrN₂O₆
• 分子量: 519.392
• InChiKey: ZJEQGOSBWVVPGS-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  33.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  110.8
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  二甲基硫 、 methyl (S)-2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-6-bromo-5-oxohexanoate 以 甲醇 为溶剂， 反应 48.0h， 以94%的产率得到(5S,8S)-5-benzyl-8-(methoxycarbonyl)-13-methyl-3,6,11-trioxo-1-phenyl-2-oxa-13-thia-4,7-diazatetradecan-13-ium 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
• 作为产物：
  描述：

  (2S)-6-bromo-5-oxo-2-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]hexanoic acid 、 三甲基硅烷化重氮甲烷 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以82%的产率得到methyl (S)-2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-6-bromo-5-oxohexanoate
  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