DB 244 | 192525-51-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: DB 244
• 英文别名: Benzenecarboximidamide, 4,4'-(2,5-furandiyl)bis[N-cyclopentyl-；N'-cyclopentyl-4-[5-[4-(N'-cyclopentylcarbamimidoyl)phenyl]furan-2-yl]benzenecarboximidamide
• CAS: 192525-51-2
• 化学式: C₂₈H₃₂N₄O
• 分子量: 440.588
• InChiKey: QWOAXYIWWNHZBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  89.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-硝基苯基2,2,2-三氯乙基碳酸酯 、 DB 244 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 24.0h， 以76%的产率得到2,5-bis[4-(N-cyclopentyl-N'-2,2,2-trichloroethoxycarbonyl)amidinophenyl]furan
  参考文献：
  名称：

  Carbamate prodrugs of N-alkylfuramidines

  摘要：

  The synthesis and evaluation of 2,5-bis[4-(N-ethoxycarbonyl-N'-isopropyl)amidinophenyl]furan, 2,5-bis[4-(N-2,2,2-trichloroethoxycarbonyl-N'-isopropyl)amidinophenyl]furan and 2,5-bis[4-(N-cyclopentyl-N'-2,2,2-trichloroethoxycarbonyl)amidinophenyl]furan as prodrugs of bis-N-alkylamidines are reported. The results show that the bis-2,2,2-trichloroethyl carbamates function effectively in a rat model for Pneumocystis pneumonia. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.03.009
• 作为产物：
  描述：

  环戊胺 、 以 乙醇 为溶剂， 反应 12.0h， 以76%的产率得到DB 244
  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

• 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
• 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.
• Carbamate prodrugs of N-alkylfuramidines
  作者：Syed M. Rahmathullah、Richard R. Tidwell、Susan K. Jones、James E. Hall、David W. Boykin

  DOI：10.1016/j.ejmech.2007.03.009

  日期：2008.1

  The synthesis and evaluation of 2,5-bis[4-(N-ethoxycarbonyl-N'-isopropyl)amidinophenyl]furan, 2,5-bis[4-(N-2,2,2-trichloroethoxycarbonyl-N'-isopropyl)amidinophenyl]furan and 2,5-bis[4-(N-cyclopentyl-N'-2,2,2-trichloroethoxycarbonyl)amidinophenyl]furan as prodrugs of bis-N-alkylamidines are reported. The results show that the bis-2,2,2-trichloroethyl carbamates function effectively in a rat model for Pneumocystis pneumonia. (C) 2007 Elsevier Masson SAS. All rights reserved.