3,7-diamidinodibenzofuran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3,7-diamidinodibenzofuran
• 英文别名: Dibenzofuran-3,7-dicarboxamidine；dibenzofuran-3,7-dicarboximidamide
• 化学式: C₁₄H₁₂N₄O
• 分子量: 252.275
• InChiKey: HGWSGYCOFMSZFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  113
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,4'-二溴-2,2'-二硝基联苯 在 Ru-carbon 盐酸 、 硫酸 、 氨 、 sodium methylate 、 一水合肼 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 377.0h， 生成 3,7-diamidinodibenzofuran
  参考文献：
  名称：

  Dicationic dibenzofuran derivatives as anti-Pneumocystis carinii pneumonia agents: synthesis, DNA binding affinity, and anti-P. carinii activity in an immunosuppressed rat model

  摘要：

  Previous work from our laboratory shows that compounds with two cations linked by a carbazole spacer were highly potent anti-P. carinii agents. A prodrug approach designed to increase oral activity of the dicationic carbazoles by converting amidine groups to amidoxime groups was unsuccessful. The ring nitrogen was implicated as playing a role in the lack of activity of carbazole amidoximes. The current study was designed to determine if replacement of the carbazole ring nitrogen by isosteric oxygen to form dibenzofurans would improve effectiveness of amidoxime prodrugs. Eight dibenzofuran dicationic derivatives were synthesized and evaluated for anti-P. carinii activity in an immunosuppressed rat model. Since DNA binding has been hypothesized to play a key role in antimicrobial activity of dicationic compounds, the compounds were examined for their binding affinity to calf thymus DNA and a poly-dA . poly-dT oligomer. While several of the compounds were more potent anti-P. carinii agents than pentamidine, the corresponding amidoximes were significantly less effective than the amidoxime of pentamidine. No direct quantitative correlation was determined between DNA binding affinity and anti-P. carinii activity, but all active compounds were strong DNA binding agents. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80054-3

文献信息

• BACTERIAL EFFLUX PUMP INHIBITORS FOR THE TREATMENT OF OPHTHALMIC AND OTIC INFECTIONS
  申请人：Bostian Keith

  公开号：US20080132457A1

  公开（公告）日：2008-06-05

  Efflux pump inhibitors are co-administered with antimicrobial agents for the treatment of ophthalmic or otic infections. The agents may be co-administered directly to the site of infection (e.g., the eye or ear).

  流出泵抑制剂与抗微生物药物一起联合使用，用于治疗眼科或耳科感染。这些药物可以直接共同应用于感染部位（例如眼睛或耳朵）。
• US7947741B2
  申请人：——

  公开号：US7947741B2

  公开（公告）日：2011-05-24
• US7994225B2
  申请人：——

  公开号：US7994225B2

  公开（公告）日：2011-08-09
• Dicationic dibenzofuran derivatives as anti-Pneumocystis carinii pneumonia agents: synthesis, DNA binding affinity, and anti-P. carinii activity in an immunosuppressed rat model
  作者：Sihe Wang、James Edwin Hall、Farial A. Tanious、W.David Wilson、Donald A. Patrick、Donald R. McCurdy、Brenden C. Bender、Richard R. Tidwell

  DOI：10.1016/s0223-5234(99)80054-3

  日期：1999.3

  Previous work from our laboratory shows that compounds with two cations linked by a carbazole spacer were highly potent anti-P. carinii agents. A prodrug approach designed to increase oral activity of the dicationic carbazoles by converting amidine groups to amidoxime groups was unsuccessful. The ring nitrogen was implicated as playing a role in the lack of activity of carbazole amidoximes. The current study was designed to determine if replacement of the carbazole ring nitrogen by isosteric oxygen to form dibenzofurans would improve effectiveness of amidoxime prodrugs. Eight dibenzofuran dicationic derivatives were synthesized and evaluated for anti-P. carinii activity in an immunosuppressed rat model. Since DNA binding has been hypothesized to play a key role in antimicrobial activity of dicationic compounds, the compounds were examined for their binding affinity to calf thymus DNA and a poly-dA . poly-dT oligomer. While several of the compounds were more potent anti-P. carinii agents than pentamidine, the corresponding amidoximes were significantly less effective than the amidoxime of pentamidine. No direct quantitative correlation was determined between DNA binding affinity and anti-P. carinii activity, but all active compounds were strong DNA binding agents. (C) Elsevier, Paris.