N-Ethyl-3,4-dihydroxy-5-nitro-benzamide | 141656-25-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-Ethyl-3,4-dihydroxy-5-nitro-benzamide
• 英文别名: N-Ethyl-3,4-dihydroxy-5-nitrobenzamide；N-ethyl-3,4-dihydroxy-5-nitrobenzamide
• CAS: 141656-25-9
• 化学式: C₉H₁₀N₂O₅
• 分子量: 226.189
• InChiKey: SIGDUVMAKGPGDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基-5-硝基苯甲酸 在 五氯化磷 、 三溴化硼 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成 N-Ethyl-3,4-dihydroxy-5-nitro-benzamide
  参考文献：
  名称：

  Synthesis and evaluation of bifunctional nitrocatechol inhibitors of pig liver catechol-O-methyltransferase

  摘要：

  Bifunctional compounds were tested in vitro as potential inhibitors of pig liver catechol-Omicron-methyltransferase (COMT) with respect to the catechol substrate 4-[(3,4-dihydroxyphenyl)azo]benzenesulfonate. The bifunctional compounds were a composite of either two nitrocatechols or one nitrocatechol and one phenol, linked by amide bonds to a spacer unit comprising two to five methylene groups. The unsymmetrical compounds N-[2-(4-hydroxybenzoylamine)ethyl]- 3,4-dihydroxy-5-nitrobenzamide], N-[3-(4-hydroxybenzoyl-amine) propyl]-3,4-dihydroxy-5-nitrobenzamide] and N-[5- (4-hydroxybenzoylamine)pentyl]-3,4-dihydroxy-5-nitrobenzamidel] demonstrated strong inhibitory action against COMT with K-i values in the 100 nM range. In comparison, the monofunctional nitrocatechol analogues of these compounds had K-i values that were significantly higher. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.069

文献信息

• Synthesis and evaluation of bifunctional nitrocatechol inhibitors of pig liver catechol-O-methyltransferase
  作者：Karl Bailey、Eng Wui Tan

  DOI：10.1016/j.bmc.2005.05.069

  日期：2005.10

  Bifunctional compounds were tested in vitro as potential inhibitors of pig liver catechol-Omicron-methyltransferase (COMT) with respect to the catechol substrate 4-[(3,4-dihydroxyphenyl)azo]benzenesulfonate. The bifunctional compounds were a composite of either two nitrocatechols or one nitrocatechol and one phenol, linked by amide bonds to a spacer unit comprising two to five methylene groups. The unsymmetrical compounds N-[2-(4-hydroxybenzoylamine)ethyl]- 3,4-dihydroxy-5-nitrobenzamide], N-[3-(4-hydroxybenzoyl-amine) propyl]-3,4-dihydroxy-5-nitrobenzamide] and N-[5- (4-hydroxybenzoylamine)pentyl]-3,4-dihydroxy-5-nitrobenzamidel] demonstrated strong inhibitory action against COMT with K-i values in the 100 nM range. In comparison, the monofunctional nitrocatechol analogues of these compounds had K-i values that were significantly higher. (c) 2005 Elsevier Ltd. All rights reserved.