N-Cyclopentyl-2-{5-[4-(N-cyclopentylcarbamimidoyl)-phenyl]-furan-2-yl}-3H-benzoimidazole-5-carboxamidine | 216308-25-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: N-Cyclopentyl-2-{5-[4-(N-cyclopentylcarbamimidoyl)-phenyl]-furan-2-yl}-3H-benzoimidazole-5-carboxamidine
• 英文别名: 1H-Benzimidazole-5-carboximidamide, N-cyclopentyl-2-(5-(4-((cyclopentylamino)iminomethyl)phenyl)-2-furanyl)-；N'-cyclopentyl-2-[5-[4-(N'-cyclopentylcarbamimidoyl)phenyl]furan-2-yl]-3H-benzimidazole-5-carboximidamide
• CAS: 216308-25-7
• 化学式: C₂₉H₃₂N₆O
• 分子量: 480.613
• InChiKey: MDWLEANZLZWRKW-UHFFFAOYSA-N

物化性质

• 沸点：
  679.4±65.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4-二氨基苯甲腈 在 盐酸 、 对苯醌 作用下， 以 乙醇 为溶剂， 反应 76.0h， 生成 N-Cyclopentyl-2-{5-[4-(N-cyclopentylcarbamimidoyl)-phenyl]-furan-2-yl}-3H-benzoimidazole-5-carboxamidine
  参考文献：
  名称：

  Extended Aromatic Furan Amidino Derivatives as Anti-Pneumocystis carinii Agents

  摘要：

  The. syntheses of nine new derivatives of 2,5-bis[4-(N-alkylamidino)phenyl]furans with extended aromatic systems are reported. The interaction of these dicationic furans with poly(dA)*poly(dT) and with the duplex oligomers d(CGCGAATTCGCG)(2) and d(GCGAATTCGC)(2) was determined by T(m) measurement, and the effectiveness of these compounds against the immunosuppressed rat model of Pneumocystis carinii was evaluated. At a screening dose of 10 mu mol/kg, 4 of the 12 amidino furans described here are more active than the parent compound 1. In general, extension of the aromatic system in the absence of a substitution of the amidino nitrogens 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 interactions in the amidino furan-DNA complex. Three of the compounds, 3, 5, and 11, yield cysts counts of less than 0.1% of control when administered at a dosage of 10 mu mol/kg. Compound 3, which does not have an extended aromatic system, is the most active derivative. Although a direct correlation between anti-P. carinii activity and DNA binding affinity was not observed, all compounds which have significant activity have large Delta T(m) values.

  DOI：

  10.1021/jm980230c

文献信息

• Extended Aromatic Furan Amidino Derivatives as Anti-<i>Pneumocystis carinii</i> Agents
  作者：Katherine T. Hopkins、W. David Wilson、Brendan C. Bender、Donald R. McCurdy、James Edwin Hall、Richard R. Tidwell、Arvind Kumar、Miro Bajic、David W. Boykin

  DOI：10.1021/jm980230c

  日期：1998.9.1

  The. syntheses of nine new derivatives of 2,5-bis[4-(N-alkylamidino)phenyl]furans with extended aromatic systems are reported. The interaction of these dicationic furans with poly(dA)*poly(dT) and with the duplex oligomers d(CGCGAATTCGCG)(2) and d(GCGAATTCGC)(2) was determined by T(m) measurement, and the effectiveness of these compounds against the immunosuppressed rat model of Pneumocystis carinii was evaluated. At a screening dose of 10 mu mol/kg, 4 of the 12 amidino furans described here are more active than the parent compound 1. In general, extension of the aromatic system in the absence of a substitution of the amidino nitrogens 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 interactions in the amidino furan-DNA complex. Three of the compounds, 3, 5, and 11, yield cysts counts of less than 0.1% of control when administered at a dosage of 10 mu mol/kg. Compound 3, which does not have an extended aromatic system, is the most active derivative. Although a direct correlation between anti-P. carinii activity and DNA binding affinity was not observed, all compounds which have significant activity have large Delta T(m) values.