[(S)-(4-Methoxy-benzylcarbamoyl)-phenyl-methyl]-carbamic acid tert-butyl ester | 765312-62-7

• 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: [(S)-(4-Methoxy-benzylcarbamoyl)-phenyl-methyl]-carbamic acid tert-butyl ester
• CAS: 765312-62-7
• 化学式: C₂₁H₂₆N₂O₄
• 分子量: 370.448
• InChiKey: CUNOEJSGBRTEJX-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  76.66
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [(S)-(4-Methoxy-benzylcarbamoyl)-phenyl-methyl]-carbamic acid tert-butyl ester 在 盐酸 、 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (S)-3-amino-2-hydroxy-N-((S)-2-((4-methoxybenzyl)amino)-2-oxo-1-phenylethyl)propanamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel L-isoserine tripeptide derivatives as aminopeptidase N inhibitors

  摘要：

  Aminopeptidase N (APN/CD13) is one of the essential proteins for tumour invasion, angiogenesis and metastasis as it is over-expressed on the surface of different tumour cells. Based on our previous work that L-isoserine dipeptide derivatives were potent APN inhibitors, we designed and synthesized L-isoserine tripeptide derivatives as APN inhibitors. Among these compounds, one compound 16l (IC50 = 2.51 +/- 0.2 +/- mu M) showed similar inhibitory effect compared with control compound Bestatin (IC50 = 6.25 +/- 0.4 mu M) and it could be used as novel lead compound for the APN inhibitors development as anticancer agents in the future.

  DOI：

  10.3109/14756366.2012.680062
• 作为产物：
  描述：

  L-苯甘氨酸 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 14.25h， 生成 [(S)-(4-Methoxy-benzylcarbamoyl)-phenyl-methyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel L-isoserine tripeptide derivatives as aminopeptidase N inhibitors

  摘要：

  Aminopeptidase N (APN/CD13) is one of the essential proteins for tumour invasion, angiogenesis and metastasis as it is over-expressed on the surface of different tumour cells. Based on our previous work that L-isoserine dipeptide derivatives were potent APN inhibitors, we designed and synthesized L-isoserine tripeptide derivatives as APN inhibitors. Among these compounds, one compound 16l (IC50 = 2.51 +/- 0.2 +/- mu M) showed similar inhibitory effect compared with control compound Bestatin (IC50 = 6.25 +/- 0.4 mu M) and it could be used as novel lead compound for the APN inhibitors development as anticancer agents in the future.

  DOI：

  10.3109/14756366.2012.680062

文献信息

• Copper dipicolinates as peptidomimetic ligands for the Src SH2 domain
  作者：Boris Schmidt、Jan Jiricek、Alexander Titz、Guofeng Ye、Keykavous Parang

  DOI：10.1016/j.bmcl.2004.06.018

  日期：2004.8

  The introduction of copper chelates into peptide mimetics creates the Src SH2 binding ligands and paramagnetic complexes suitable for EPR studies of peptide protein interactions. The dipicolinic acid was attached to SH2 domain targeting fragments by two different linkers. (C) 2004 Elsevier Ltd. All rights reserved.