(2S,3R)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-nitrophenyl)propanoic acid

• 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: (2S,3R)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-nitrophenyl)propanoic acid
• 化学式: C₁₄H₁₈N₂O₇
• 分子量: 326.306
• InChiKey: JHJOGYYIDLAMQW-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  142
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-nitrophenyl)propanoic acid 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 18.25h， 生成
  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：

  二碳酸二叔丁酯 、 (2S,3R)-2-amino-3-hydroxy-3-(4-aminophenyl)propanoic acid 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (2S,3R)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-nitrophenyl)propanoic acid
  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

• Design, synthesis and biological evaluation of novel <i>L</i>-isoserine tripeptide derivatives as aminopeptidase N inhibitors
  作者：Huili Pan、Kanghui Yang、Jian Zhang、Yingying Xu、Yuqi Jiang、Yumei Yuan、Xiaopan Zhang、Wenfang Xu

  DOI：10.3109/14756366.2012.680062

  日期：2013.8.1

  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.