[1-(1-{1-[(2-oxo-1,4-diphenyl-azetidin-3-ylmethyl)-carbamoyl]-ethylcarbamoyl}-ethylcarbamoyl)ethyl]-carbamic acid tert-butyl ester | 1261612-79-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: [1-(1-{1-[(2-oxo-1,4-diphenyl-azetidin-3-ylmethyl)-carbamoyl]-ethylcarbamoyl}-ethylcarbamoyl)ethyl]-carbamic acid tert-butyl ester
• CAS: 1261612-79-6
• 化学式: C₃₀H₃₉N₅O₆
• 分子量: 565.67
• InChiKey: KWRBIEXRQAUTMW-RPBUIGJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  145.94
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [1-(1-{1-[(2-oxo-1,4-diphenyl-azetidin-3-ylmethyl)-carbamoyl]-ethylcarbamoyl}-ethylcarbamoyl)ethyl]-carbamic acid tert-butyl ester 在 三氟乙酸 、 sodium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 以72%的产率得到2-amino-N-(1-{1-[(2-oxo-1,4-diphenyl-azetidin-3-ylmethyl)-carbamoyl]-ethylcarbamoyl}-ethyl)-propionamide
  参考文献：
  名称：

  Design, synthesis and inhibition activity of novel cyclic peptides against protein tyrosine phosphatase A from Mycobacterium tuberculosis

  摘要：

  Mycobacterium tuberculosis, the causative agent for tuberculosis has employed several signalling molecules to sense the host cellular environment and act accordingly. For example, protein tyrosine phosphatase A (MPtpA) of M. tuberculosis, a signalling protein belonging to the tyrosine phosphatase superfamily, is involved in phagocytosis and is active in virulent mycobacterial form. Starting from a beta-lactam framework a new class of structure based cyclic peptide (CP) inhibitors was designed. The synthesis involves a crucial intramolecular transamidation via a ring opening reaction. All the compounds show moderate to good inhibitory activities against MPtpA in micromolar concentrations. The results of inhibition kinetics suggest mixed mode of inhibition. The binding constant determined from circular dichroism (CD) and fluorescence quenching studies shows strong binding of the hydrophilic side chain of CPs with the enzyme active site residues. All these are well supported by docking studies. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.052
• 作为产物：
  描述：

  3-aminomethyl-1,4-diphenyl-azetidin-2-one 、 Boc-Ala-Ala-Ala-OH 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到[1-(1-{1-[(2-oxo-1,4-diphenyl-azetidin-3-ylmethyl)-carbamoyl]-ethylcarbamoyl}-ethylcarbamoyl)ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Design, synthesis and inhibition activity of novel cyclic peptides against protein tyrosine phosphatase A from Mycobacterium tuberculosis

  摘要：

  Mycobacterium tuberculosis, the causative agent for tuberculosis has employed several signalling molecules to sense the host cellular environment and act accordingly. For example, protein tyrosine phosphatase A (MPtpA) of M. tuberculosis, a signalling protein belonging to the tyrosine phosphatase superfamily, is involved in phagocytosis and is active in virulent mycobacterial form. Starting from a beta-lactam framework a new class of structure based cyclic peptide (CP) inhibitors was designed. The synthesis involves a crucial intramolecular transamidation via a ring opening reaction. All the compounds show moderate to good inhibitory activities against MPtpA in micromolar concentrations. The results of inhibition kinetics suggest mixed mode of inhibition. The binding constant determined from circular dichroism (CD) and fluorescence quenching studies shows strong binding of the hydrophilic side chain of CPs with the enzyme active site residues. All these are well supported by docking studies. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.052