{5-hydroxycarbamoyl-5-[3-(1-hydroxycarbamoyl-2-phenyl-ethyl)-ureido]-pentyl}-carbamic acid benzyl ester | 1244610-19-2

• 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: {5-hydroxycarbamoyl-5-[3-(1-hydroxycarbamoyl-2-phenyl-ethyl)-ureido]-pentyl}-carbamic acid benzyl ester
• 英文别名: benzyl(S)-6-(hydroxyamino)-5-(3-((S)-1-(hydroxyamino)-1-oxo-3-phenylpropan-2-yl)ureido)-6-oxohexylcarbamate；benzyl N-[(5S)-6-(hydroxyamino)-5-[[(2S)-1-(hydroxyamino)-1-oxo-3-phenylpropan-2-yl]carbamoylamino]-6-oxohexyl]carbamate
• CAS: 1244610-19-2
• 化学式: C₂₄H₃₁N₅O₇
• 分子量: 501.539
• InChiKey: VXVBTUBOZYIIEH-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  178
• 氢给体数：
  7
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (S)-6-Benzyloxycarbonylamino-2-[3-((S)-1-methoxycarbonyl-2-phenyl-ethyl)-ureido]-hexanoic acid methyl ester 在 羟胺钾盐 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以35%的产率得到{5-hydroxycarbamoyl-5-[3-(1-hydroxycarbamoyl-2-phenyl-ethyl)-ureido]-pentyl}-carbamic acid benzyl 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.