(S)-5-amino-2-(3-((S)-1-methoxy-4-methyl-1-oxopentan-2-yl)ureido)-5-oxopentanoic acid | 1208237-21-1

• 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: (S)-5-amino-2-(3-((S)-1-methoxy-4-methyl-1-oxopentan-2-yl)ureido)-5-oxopentanoic acid
• CAS: 1208237-21-1
• 化学式: C₁₃H₂₃N₃O₆
• 分子量: 317.342
• InChiKey: WCGBKZHSVWXMRR-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.41
• 重原子数：
  22.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  147.82
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  L-谷氨酰胺 、 (S)-(-)-2-异氰酰基-4-甲基戊酸甲酯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-5-amino-2-(3-((S)-1-methoxy-4-methyl-1-oxopentan-2-yl)ureido)-5-oxopentanoic acid
  参考文献：
  名称：

  Bioisosterism of urea-based GCPII inhibitors: Synthesis and structure–activity relationship studies

  摘要：

  We report a strategy based on bioisosterism to improve the physicochemical properties of existing hydrophilic, urea-based GCPII inhibitors. Comprehensive structure-activity relationship studies of the P1' site of ZJ-43- and DCIBzL-based compounds identified several glutamate-free inhibitors with K-i values below 20 nM. Among them, compound 32d (K-i = 11 nM) exhibited selective uptake in GCPII-expressing tumors by SPECT-CT imaging in mice. A novel conformational change of amino acids in the S1' pharmacophore pocket was observed in the X-ray crystal structure of GCPII complexed with 32d. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.061