tert-butyl 3-<(tert-butoxycarbonyl)amino>-4-oxo-5-diazopentanoate | 128135-32-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-butyl 3-<(tert-butoxycarbonyl)amino>-4-oxo-5-diazopentanoate
• 英文别名: tert-butyl 3-[(tert-butoxycarbonyl)amino]-4-oxo-5-diazopentanoate
• CAS: 128135-32-0
• 化学式: C₁₄H₂₃N₃O₅
• 分子量: 313.354
• InChiKey: AOTAEQHPXMWTJW-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  118.1
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 tert-butyl 3-<(tert-butoxycarbonyl)amino>-4-oxo-5-diazopentanoate 在 silver benzoate 、 三乙胺 作用下， 反应 16.0h， 以39%的产率得到tert-butyl methyl 3-<(tert-butoxycarbonyl)amino>pentanedioate
  参考文献：
  名称：

  Synthesis of acyclic and dehydroaspartic acid analogs of Ac-Asp-Glu-OH and their inhibition of rat brain N-acetylated .alpha.-linked acidic dipeptidase (NAALA dipeptidase)

  摘要：

  The following structural and conformationally constrained analogues of Ac-Asp-Glu-OH (1) were synthesized: Ac-Glu-Glu-OH (2), Ac-D-Asp-Glu-OH (3), Ac-Glu-Asp-OH (4), Ac-Asp-Asp-OH (5), Ac-Asp-3-aminohexanedioic acid (6), Ac-3-amino-3-(carboxymethyl)propanoyl-Glu-OH (7), N-succinyl-Glu-OH (8), N-maleyl-Glu-OH (9), N-fumaryl-Glu-OH (10), and Ac-delta ZAsp-Glu-OH (11). These analogues were evaluated for their ability to inhibit the hydrolysis of Ac-Asp-[3,4-3H]-Glu-OH by N-acetylated alpha-linked acidic dipeptidase (NAALA dipeptidase) in order to gain some insight into the structural requirements for the inhibition of this enzyme. Analogues 4-6 and 9 were very weak inhibitors of NAALA dipeptidase (Ki greater than 40 microM), while 2, 3, and 7 with Ki values ranging from 3.2-8.5 microM showed intermediate inhibitory activity. The most active inhibitors of NAALA dipeptidase were compounds 8, 10, and 11 with Ki values of 0.9, 0.4, and 1.4 microM, respectively. These results suggest that the relative spacing between the side chain carboxyl and the alpha-carboxyl group of the C-terminal residue may be important for binding to the active site of the enzyme. They also indicate that the chi 1 torsional angle for the aspartyl residue is in the vicinity of 0 degrees.

  DOI：

  10.1021/jm00172a009
• 作为产物：
  描述：

  重氮甲烷 、 叔丁氧羰基-L-天冬氨酸-4-叔丁酯 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 生成 tert-butyl 3-<(tert-butoxycarbonyl)amino>-4-oxo-5-diazopentanoate
  参考文献：
  名称：

  Synthesis of acyclic and dehydroaspartic acid analogs of Ac-Asp-Glu-OH and their inhibition of rat brain N-acetylated .alpha.-linked acidic dipeptidase (NAALA dipeptidase)

  摘要：

  The following structural and conformationally constrained analogues of Ac-Asp-Glu-OH (1) were synthesized: Ac-Glu-Glu-OH (2), Ac-D-Asp-Glu-OH (3), Ac-Glu-Asp-OH (4), Ac-Asp-Asp-OH (5), Ac-Asp-3-aminohexanedioic acid (6), Ac-3-amino-3-(carboxymethyl)propanoyl-Glu-OH (7), N-succinyl-Glu-OH (8), N-maleyl-Glu-OH (9), N-fumaryl-Glu-OH (10), and Ac-delta ZAsp-Glu-OH (11). These analogues were evaluated for their ability to inhibit the hydrolysis of Ac-Asp-[3,4-3H]-Glu-OH by N-acetylated alpha-linked acidic dipeptidase (NAALA dipeptidase) in order to gain some insight into the structural requirements for the inhibition of this enzyme. Analogues 4-6 and 9 were very weak inhibitors of NAALA dipeptidase (Ki greater than 40 microM), while 2, 3, and 7 with Ki values ranging from 3.2-8.5 microM showed intermediate inhibitory activity. The most active inhibitors of NAALA dipeptidase were compounds 8, 10, and 11 with Ki values of 0.9, 0.4, and 1.4 microM, respectively. These results suggest that the relative spacing between the side chain carboxyl and the alpha-carboxyl group of the C-terminal residue may be important for binding to the active site of the enzyme. They also indicate that the chi 1 torsional angle for the aspartyl residue is in the vicinity of 0 degrees.

  DOI：

  10.1021/jm00172a009

文献信息

• SUBASINGHE, NALIN;SCHULTE, MARVIN;CHAN, MICHAEL Y. -M.;ROON, ROBERT J.;KO+, J. MED. CHEM., 33,(1990) N0, C. 2734-2744
  作者：SUBASINGHE, NALIN、SCHULTE, MARVIN、CHAN, MICHAEL Y. -M.、ROON, ROBERT J.、KO+

  DOI：——

  日期：——