2-(3-phenethyl-ureido)-4-(N-benzyloxycarbonyl)-aminobutyl-acetic acid methyl ester | 1268836-02-7

• 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: 2-(3-phenethyl-ureido)-4-(N-benzyloxycarbonyl)-aminobutyl-acetic acid methyl ester
• 英文别名: methyl (2S)-2-(2-phenylethylcarbamoylamino)-6-(phenylmethoxycarbonylamino)hexanoate
• CAS: 1268836-02-7
• 化学式: C₂₄H₃₁N₃O₅
• 分子量: 441.527
• InChiKey: IMNHGEDOARICPT-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3-phenethyl-ureido)-4-(N-benzyloxycarbonyl)-aminobutyl-acetic acid methyl ester 在 羟胺钾盐 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以38.8%的产率得到(S)-benzyl 6-(hydroxyamino)-6-oxo-5-(3-phenethylureido)hexylcarbamate
  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：

  2-苯乙基异氰酸酯 、 CBZ-L-赖氨酸甲酯盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以65.8%的产率得到2-(3-phenethyl-ureido)-4-(N-benzyloxycarbonyl)-aminobutyl-acetic acid methyl ester
  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

文献信息

• Design, synthesis and biological evaluation of novel l-lysine ureido derivatives as aminopeptidase N inhibitors
  作者：Li Su、Hao Fang、Kanghui Yang、Yingying Xu、Wenfang Xu

  DOI：10.1016/j.bmc.2010.11.066

  日期：2011.1

  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.