N-[2-[(3,4-dimethoxybenzoyl)amino]ethyl]-3,4-dimethoxybenzamide | 548448-54-0

• 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: N-[2-[(3,4-dimethoxybenzoyl)amino]ethyl]-3,4-dimethoxybenzamide
• CAS: 548448-54-0
• 化学式: C₂₀H₂₄N₂O₆
• 分子量: 388.42
• InChiKey: PMRQLJRIJRDPJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  95.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[2-[(3,4-dimethoxybenzoyl)amino]ethyl]-3,4-dimethoxybenzamide 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 N,N'-bisprotocatechuoyl 1,2-diaminoethane
  参考文献：
  名称：

  Synthesis and in Vitro Evaluation of Two Progressive Series of Bifunctional Polyhydroxybenzamide Catechol-O-methyltransferase Inhibitors

  摘要：

  Two progressive series of molecules with two polyhydroxybenzamide substructures were synthesized and tested as potential inhibitors of catechol-O-methyltransferase (COMT). These compounds were designed for the purpose of enhanced enzyme binding with duplicated substructures separated by a linker section of various lengths. Our results show that potency and mode of inhibition observed with the ''bifunctional'' compounds were a reflection of their bifunctional nature. Furthermore, potency and mode of inhibition were dependent on the length of the linker section. Of the assayed compounds, the optimum linker was found to be diaminopropane. For example, N,N'-1,3-propanediylbis(3,4-dihydroxybenzamide) and N,N'-1,3-propanediylbis(3,4,5-trihydroxybenzamide) demonstrated strong inhibitory action against COMT, with apparent K-i values of 0.3 and 6.0 mu M, respectively.

  DOI：

  10.1021/jm9605187
• 作为产物：
  描述：

  藜芦酸 在 五氯化磷 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 N-[2-[(3,4-dimethoxybenzoyl)amino]ethyl]-3,4-dimethoxybenzamide
  参考文献：
  名称：

  Synthesis and in Vitro Evaluation of Two Progressive Series of Bifunctional Polyhydroxybenzamide Catechol-O-methyltransferase Inhibitors

  摘要：

  Two progressive series of molecules with two polyhydroxybenzamide substructures were synthesized and tested as potential inhibitors of catechol-O-methyltransferase (COMT). These compounds were designed for the purpose of enhanced enzyme binding with duplicated substructures separated by a linker section of various lengths. Our results show that potency and mode of inhibition observed with the ''bifunctional'' compounds were a reflection of their bifunctional nature. Furthermore, potency and mode of inhibition were dependent on the length of the linker section. Of the assayed compounds, the optimum linker was found to be diaminopropane. For example, N,N'-1,3-propanediylbis(3,4-dihydroxybenzamide) and N,N'-1,3-propanediylbis(3,4,5-trihydroxybenzamide) demonstrated strong inhibitory action against COMT, with apparent K-i values of 0.3 and 6.0 mu M, respectively.

  DOI：

  10.1021/jm9605187

文献信息

• Synthesis and <i>in Vitro</i> Evaluation of Two Progressive Series of Bifunctional Polyhydroxybenzamide Catechol-<i>O</i>-methyltransferase Inhibitors
  作者：Sharon E. Brevitt、Eng Wui Tan

  DOI：10.1021/jm9605187

  日期：1997.6.1

  Two progressive series of molecules with two polyhydroxybenzamide substructures were synthesized and tested as potential inhibitors of catechol-O-methyltransferase (COMT). These compounds were designed for the purpose of enhanced enzyme binding with duplicated substructures separated by a linker section of various lengths. Our results show that potency and mode of inhibition observed with the ''bifunctional'' compounds were a reflection of their bifunctional nature. Furthermore, potency and mode of inhibition were dependent on the length of the linker section. Of the assayed compounds, the optimum linker was found to be diaminopropane. For example, N,N'-1,3-propanediylbis(3,4-dihydroxybenzamide) and N,N'-1,3-propanediylbis(3,4,5-trihydroxybenzamide) demonstrated strong inhibitory action against COMT, with apparent K-i values of 0.3 and 6.0 mu M, respectively.