ethyl 6,8-dichloro-2-(4-fluorophenyl)-4-hydroxy-3,4-dihydro-2H-chromene-3-carboxylate | 1448552-76-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: ethyl 6,8-dichloro-2-(4-fluorophenyl)-4-hydroxy-3,4-dihydro-2H-chromene-3-carboxylate
• CAS: 1448552-76-8
• 化学式: C₁₈H₁₅Cl₂FO₄
• 分子量: 385.219
• InChiKey: SQLDTKNBXHKDKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 6,8-dichloro-2-(4-fluorophenyl)-4-hydroxy-3,4-dihydro-2H-chromene-3-carboxylate 在 对甲苯磺酸 作用下， 以64%的产率得到ethyl 6,8-dichloro-2-(4-fluorophenyl)-2H-chromene-3-carboxylate
  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
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 生成 ethyl 6,8-dichloro-2-(4-fluorophenyl)-4-hydroxy-3,4-dihydro-2H-chromene-3-carboxylate
  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