DB249 | 192525-52-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: DB249
• 英文别名: 2,5-bis[4-(N-cyclohexylamidino)phenyl]-furan；Benzenecarboximidamide, 4,4'-(2,5-furandiyl)bis[N-cyclohexyl-；N'-cyclohexyl-4-[5-[4-(N'-cyclohexylcarbamimidoyl)phenyl]furan-2-yl]benzenecarboximidamide
• CAS: 192525-52-3
• 化学式: C₃₀H₃₆N₄O
• 分子量: 468.642
• InChiKey: UJNPVYRWQJDTBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  89.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  环己胺 、 以 乙醇 为溶剂， 反应 12.0h， 以78%的产率得到DB249
  参考文献：
  名称：

  2,5-Bis[4-(N-alkylamidino)phenyl]furans as Anti-Pneumocystis carinii Agents

  摘要：

  The syntheses of 12 new 2,5-bis[4-(N-alkylamidino)phenyl]furans are reported. The interaction of these dicationic furans with poly(dA-dT) and with the duplex oligomer d(CGCGAATTCGCG)(2) was determined by T-m measurements, and the effectiveness of these compounds against the immunosuppressed rat model of Pneumocystis carinii was evaluated. At the screening dose of 10 mu mol/kg, 9 of the 14 N-alkylamidino furans described here are more active than the parent compound 1. Substitution of an alkyl group on the amidino nitrogen, except for in 9, 13, and 15, resulted in higher affinity for DNA than the parent compound as judged by the larger Delta T-m values and suggests enhanced van der Waals interact ions in the bis-amidine-DNA complex. Five of the compounds, 3, 5, 7, 10, and 12, yield cyst counts of less than 0.1% of control when administered at a dosage of 10 mu mol/kg. Five compounds, 1, 6, 8, 10, and 12, show significant activity at a dosage of approximately 1 mu mol/kg; 12 is the most active derivative, and it is approximately 100 times more effective than pentamidine in this animal model.

  DOI：

  10.1021/jm970570i

文献信息

• Dicationic Compounds For Activity Against Trichomonas Vaginalis
  申请人：Boykin W. David

  公开号：US20070276020A1

  公开（公告）日：2007-11-29

  Dicationic compounds for the treatment of T. vaginalis infections are described. The presently described compounds exhibit in vitro activity against metronidazole-sensitive and -resistant T. vaginalis isolates. Furthermore, the presently described compounds demonstrate IC 50 concentrations that were not elevated in the metronidazole resistant isolate, suggesting that their activity is not affected by parasite mechanisms that confer resistance to 5-nitroimidizoles.

  本文描述了用于治疗T. vaginalis感染的二价化合物。目前描述的化合物在体外对甲硝唑敏感和耐药的T. vaginalis分离株具有活性。此外，目前描述的化合物表现出的IC50浓度在甲硝唑耐药分离株中没有升高，表明它们的活性不受寄生虫机制的影响，这些机制使其对5-硝基咪唑类药物产生耐药性。
• 2,5-Bis[4-(<i>N</i>-alkylamidino)phenyl]furans as Anti-<i>Pneumocystis carinii</i> Agents
  作者：David W. Boykin、Arvind Kumar、Ge Xiao、W. David Wilson、Brendan C. Bender、Donald R. McCurdy、James Edwin Hall、Richard R. Tidwell

  DOI：10.1021/jm970570i

  日期：1998.1.1

  The syntheses of 12 new 2,5-bis[4-(N-alkylamidino)phenyl]furans are reported. The interaction of these dicationic furans with poly(dA-dT) and with the duplex oligomer d(CGCGAATTCGCG)(2) was determined by T-m measurements, and the effectiveness of these compounds against the immunosuppressed rat model of Pneumocystis carinii was evaluated. At the screening dose of 10 mu mol/kg, 9 of the 14 N-alkylamidino furans described here are more active than the parent compound 1. Substitution of an alkyl group on the amidino nitrogen, except for in 9, 13, and 15, resulted in higher affinity for DNA than the parent compound as judged by the larger Delta T-m values and suggests enhanced van der Waals interact ions in the bis-amidine-DNA complex. Five of the compounds, 3, 5, 7, 10, and 12, yield cyst counts of less than 0.1% of control when administered at a dosage of 10 mu mol/kg. Five compounds, 1, 6, 8, 10, and 12, show significant activity at a dosage of approximately 1 mu mol/kg; 12 is the most active derivative, and it is approximately 100 times more effective than pentamidine in this animal model.