methyl (2S)-2-[[(2S)-1-methoxy-4-methylsulfanyl-1-oxobutan-2-yl]carbamoylamino]-6-(phenylmethoxycarbonylamino)hexanoate | 1244610-34-1

• 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 (2S)-2-[[(2S)-1-methoxy-4-methylsulfanyl-1-oxobutan-2-yl]carbamoylamino]-6-(phenylmethoxycarbonylamino)hexanoate
• CAS: 1244610-34-1
• 化学式: C₂₂H₃₃N₃O₇S
• 分子量: 483.586
• InChiKey: VLSUXYQNVMNZRF-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  33
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  157
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[[(2S)-1-methoxy-4-methylsulfanyl-1-oxobutan-2-yl]carbamoylamino]-6-(phenylmethoxycarbonylamino)hexanoate 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 以34.7%的产率得到6-benzyloxycarbonylamino-2-[3-(1-carboxy-3-methylsulfanyl-propyl)-ureido]-hexanoic acid
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel l-lysine ureido derivatives as aminopeptidase N inhibitors

  摘要：

  As the exopeptidase over-expressed in the cell surface of endothelial cells, aminopeptidase N (APN/CD13) is an essential target for tumor angiogenesis and metastasis. Based on the previous work of L-lysine amide derivatives in our laboratory, we designed and synthesized two series of L-lysine ureido derivatives as APN inhibitors. Within these compounds, one compound, 5d (IC50 = 4.51 mu M), showed similar inhibitory effect compared with Bestatin (IC50 = 5.87 mu M). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.066
• 作为产物：
  描述：

  CBZ-L-赖氨酸甲酯盐酸盐 在 碳酸氢钠 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.75h， 生成 methyl (2S)-2-[[(2S)-1-methoxy-4-methylsulfanyl-1-oxobutan-2-yl]carbamoylamino]-6-(phenylmethoxycarbonylamino)hexanoate
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel l-lysine ureido derivatives as aminopeptidase N inhibitors

  摘要：

  As the exopeptidase over-expressed in the cell surface of endothelial cells, aminopeptidase N (APN/CD13) is an essential target for tumor angiogenesis and metastasis. Based on the previous work of L-lysine amide derivatives in our laboratory, we designed and synthesized two series of L-lysine ureido derivatives as APN inhibitors. Within these compounds, one compound, 5d (IC50 = 4.51 mu M), showed similar inhibitory effect compared with Bestatin (IC50 = 5.87 mu M). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.066