5-methoxynaphtho[2,3-c]furan-1,3-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 5-methoxynaphtho[2,3-c]furan-1,3-dione
• 英文别名: 5-Methoxybenzo[f][2]benzofuran-1,3-dione；5-methoxybenzo[f][2]benzofuran-1,3-dione
• 化学式: C₁₃H₈O₄
• 分子量: 228.204
• InChiKey: NWUYCZFXVRWCLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对三氟甲氧基苯胺 、 5-methoxynaphtho[2,3-c]furan-1,3-dione 在 吡啶 作用下， 反应 12.0h， 以31.3%的产率得到5-methoxy-N-(4-(trifluoromethoxy)phenyl)-2,3-naphthalimide
  参考文献：
  名称：

  Design, synthesis and evaluation of a series of 5-methoxy-2,3-naphthalimide derivatives as AcrB inhibitors for the reversal of bacterial resistance

  摘要：

  A series of novel 5-methoxy-2,3-naphthalimide derivatives were designed, synthesized and evaluated for their biological activities. In particular, the ability of the compounds to synergize with antimicrobials, to inhibit Nile Red efflux, and to target AcrB was assayed. The results showed that the most of the tested compounds more sensitized the Escherichia coli BW25113 to the antibiotics than the parent compounds 7 c and 15, which were able to inhibit Nile Red efflux. Significantly, compound A5 possessed the most potent antibacterial synergizing ac-tivity in combination with levofloxacin by 4 times and 16 times at the concentration of 8 and 16 mu g/mL, re-spectively, whilst A5 could effectively abolish Nile Red efflux at 100 mu M. Additionally, target effect of A5 was confirmed in the outer- or inner membrane permeabilization assays. Therefore, A5 is an excellent lead com-pound for further structural optimization.

  DOI：

  10.1016/j.bmcl.2019.02.003
• 作为产物：
  描述：

  二甲酚 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 potassium carbonate 、 碘甲烷 作用下， 以 四氯化碳 、 乙酸酐 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 5-methoxynaphtho[2,3-c]furan-1,3-dione
  参考文献：
  名称：

  2,3-萘二甲酰亚胺类衍生物及其制备方法和 应用

  摘要：

  本发明提供一种化合物或其可药用盐及其制备方法和应用，所述化合物对过表达AcrB的格兰阴性菌具有较好的抗菌增效活性及外排抑制活性。

  公开号：

  CN108929260B

文献信息

• 2,3-萘二甲酰亚胺类衍生物及其制备方法和 应用
  申请人：山东大学

  公开号：CN108929260B

  公开（公告）日：2020-05-26

  本发明提供一种化合物或其可药用盐及其制备方法和应用，所述化合物对过表达AcrB的格兰阴性菌具有较好的抗菌增效活性及外排抑制活性。
• Design, synthesis and evaluation of a series of 5-methoxy-2,3-naphthalimide derivatives as AcrB inhibitors for the reversal of bacterial resistance
  作者：Chaobin Jin、Rawaf Alenazy、Yinhu Wang、Rumana Mowla、Yinhui Qin、Jin Quan Eugene Tan、Natansh Deepak Modi、Xinjie Gu、Steven W. Polyak、Henrietta Venter、Shutao Ma

  DOI：10.1016/j.bmcl.2019.02.003

  日期：2019.4

  A series of novel 5-methoxy-2,3-naphthalimide derivatives were designed, synthesized and evaluated for their biological activities. In particular, the ability of the compounds to synergize with antimicrobials, to inhibit Nile Red efflux, and to target AcrB was assayed. The results showed that the most of the tested compounds more sensitized the Escherichia coli BW25113 to the antibiotics than the parent compounds 7 c and 15, which were able to inhibit Nile Red efflux. Significantly, compound A5 possessed the most potent antibacterial synergizing ac-tivity in combination with levofloxacin by 4 times and 16 times at the concentration of 8 and 16 mu g/mL, re-spectively, whilst A5 could effectively abolish Nile Red efflux at 100 mu M. Additionally, target effect of A5 was confirmed in the outer- or inner membrane permeabilization assays. Therefore, A5 is an excellent lead com-pound for further structural optimization.