dimethyl 2,2'-(2-hydroxy-1,3-phenylene)bis(2-oxoacetate) | 1366768-06-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl 2,2'-(2-hydroxy-1,3-phenylene)bis(2-oxoacetate)
• 英文别名: Methyl 2-[2-hydroxy-3-(2-methoxy-2-oxoacetyl)phenyl]-2-oxoacetate
• CAS: 1366768-06-0
• 化学式: C₁₂H₁₀O₇
• 分子量: 266.207
• InChiKey: NLMPIJLVRUDALO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl 2,2'-(2-hydroxy-1,3-phenylene)bis(2-oxoacetate) 在 lithium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 以67%的产率得到2,2'-(2-hydroxy-1,3-phenylene)bis(2-oxoacetic acid)
  参考文献：
  名称：

  1,3-Phenylene bis(ketoacid) derivatives as inhibitors of Escherichia coli dihydrodipicolinate synthase

  摘要：

  Dihydrodipicolinate synthase is a key enzyme in the lysine biosynthesis pathway that catalyzes the condensation of pyruvate and aspartate semi-aldehyde. A series of phenolic ketoacid derivatives that mimic the proposed enzymatic intermediate were designed as potential inhibitors of this enzyme and were synthesized from simple precursors. The ketoacid derivatives were shown to act as slow and slow-tight binding inhibitors. Mass spectrometric experiments provided further evidence to support the proposed model of inhibition, demonstrating either an encounter complex or a condensation product for the slow and slow-tight binding inhibitors, respectively. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.045
• 作为产物：
  描述：

  dimethyl 2,2'-(2-methoxy-1,3-phenylene)bis(2-oxoacetate) 在 乙硫醇钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以36%的产率得到dimethyl 2,2'-(2-hydroxy-1,3-phenylene)bis(2-oxoacetate)
  参考文献：
  名称：

  1,3-Phenylene bis(ketoacid) derivatives as inhibitors of Escherichia coli dihydrodipicolinate synthase

  摘要：

  Dihydrodipicolinate synthase is a key enzyme in the lysine biosynthesis pathway that catalyzes the condensation of pyruvate and aspartate semi-aldehyde. A series of phenolic ketoacid derivatives that mimic the proposed enzymatic intermediate were designed as potential inhibitors of this enzyme and were synthesized from simple precursors. The ketoacid derivatives were shown to act as slow and slow-tight binding inhibitors. Mass spectrometric experiments provided further evidence to support the proposed model of inhibition, demonstrating either an encounter complex or a condensation product for the slow and slow-tight binding inhibitors, respectively. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.045

文献信息

• 1,3-Phenylene bis(ketoacid) derivatives as inhibitors of Escherichia coli dihydrodipicolinate synthase
  作者：Berin A. Boughton、Lilian Hor、Juliet A. Gerrard、Craig A. Hutton

  DOI：10.1016/j.bmc.2012.01.045

  日期：2012.4

  Dihydrodipicolinate synthase is a key enzyme in the lysine biosynthesis pathway that catalyzes the condensation of pyruvate and aspartate semi-aldehyde. A series of phenolic ketoacid derivatives that mimic the proposed enzymatic intermediate were designed as potential inhibitors of this enzyme and were synthesized from simple precursors. The ketoacid derivatives were shown to act as slow and slow-tight binding inhibitors. Mass spectrometric experiments provided further evidence to support the proposed model of inhibition, demonstrating either an encounter complex or a condensation product for the slow and slow-tight binding inhibitors, respectively. (C) 2012 Elsevier Ltd. All rights reserved.