4-methoxy-N-[2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)sulfanyl]ethyl]benzamide | 1448552-73-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: 4-methoxy-N-[2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)sulfanyl]ethyl]benzamide
• CAS: 1448552-73-5
• 化学式: C₁₆H₁₄N₄O₅S
• 分子量: 374.377
• InChiKey: NFMPTEWSGVVPAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-(2-mercaptoethyl)-4-methoxybenzamide 、 4-氯-7-硝基苯并-2-氧杂-1,3-二唑 在 三乙胺 作用下， 以54%的产率得到4-methoxy-N-[2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)sulfanyl]ethyl]benzamide
  参考文献：
  名称：

  Improved Flavodoxin Inhibitors with Potential Therapeutic Effects against Helicobacter pylori Infection

  摘要：

  Helicobacter pylori (Hp) infection affects one-half of the human population and produces a variety of diseases from peptic ulcer to cancer. Current eradication therapies achieve modest success rates (around 70%), resistance to the antibiotics of choice is on the rise, and vaccination has not proved to be successful yet. Using an essential Hp protein, flavodoxin, as target, we identified three low-molecular-weight flavodoxin inhibitors with bactericidal anti-Hp properties. To improve their therapeutic indexes, we have now identified and tested 123 related compounds. We have first tested similar compounds available. Then we have designed, synthesized, and tested novel variants for affinity to flavodoxin, MIC for Hp, cytotoxicity, and bactericidal effect. Some are novel bactericidal inhibitors with therapeutic indexes of 9, 38 and 12, significantly higher than those of their corresponding leads. Developing novel Hp-specific antibiotics will help fighting Hp resistance and may have the advantage of not generally perturbing the bacterial flora.

  DOI：

  10.1021/jm400786q

文献信息

• Improved Flavodoxin Inhibitors with Potential Therapeutic Effects against <i>Helicobacter pylori</i> Infection
  作者：Juan J. Galano、Miriam Alías、Reyes Pérez、Adrian Velázquez-Campoy、Paul S. Hoffman、Javier Sancho

  DOI：10.1021/jm400786q

  日期：2013.8.8

  Helicobacter pylori (Hp) infection affects one-half of the human population and produces a variety of diseases from peptic ulcer to cancer. Current eradication therapies achieve modest success rates (around 70%), resistance to the antibiotics of choice is on the rise, and vaccination has not proved to be successful yet. Using an essential Hp protein, flavodoxin, as target, we identified three low-molecular-weight flavodoxin inhibitors with bactericidal anti-Hp properties. To improve their therapeutic indexes, we have now identified and tested 123 related compounds. We have first tested similar compounds available. Then we have designed, synthesized, and tested novel variants for affinity to flavodoxin, MIC for Hp, cytotoxicity, and bactericidal effect. Some are novel bactericidal inhibitors with therapeutic indexes of 9, 38 and 12, significantly higher than those of their corresponding leads. Developing novel Hp-specific antibiotics will help fighting Hp resistance and may have the advantage of not generally perturbing the bacterial flora.