2,5-bis(4-N,N'-di-BOCguanidinophenyl)furan | 347190-87-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 2,5-bis(4-N,N'-di-BOCguanidinophenyl)furan
• 英文别名: tert-butyl N-[[4-[5-[4-[[N,N'-bis[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]amino]phenyl]furan-2-yl]anilino]-[(2-methylpropan-2-yl)oxycarbonylamino]methylidene]carbamate
• CAS: 347190-87-8
• 化学式: C₃₈H₅₀N₆O₉
• 分子量: 734.85
• InChiKey: SVTAVGZUOIKARG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  53
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  191
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,5-bis(4-N,N'-di-BOCguanidinophenyl)furan 在 盐酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 DB673
  参考文献：
  名称：

  The activity of diguanidino and ‘reversed’ diamidino 2,5-diarylfurans versus Trypanosoma cruzi and Leishmania donovani

  摘要：

  The in vitro activity of 20 dicationic molecules containing either diguanidino or reversed amidine cationic groups were evaluated versus Trypanosoma cruzi and Leishmania donovani. The most active compounds were in the reversed amidine series and six exhibited IC50 values of less than 1 mumol versus T. cruzi and five gave similar values versus L. donovani. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00319-6
• 作为产物：
  描述：

  2,5-bis(4-nitrophenyl)furan 在 10percent Pd/C 氢气 、 三乙胺 、 mercury dichloride 作用下， 以 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 22.0h， 生成 2,5-bis(4-N,N'-di-BOCguanidinophenyl)furan
  参考文献：
  名称：

  Diguanidino and “Reversed” Diamidino 2,5-Diarylfurans as Antimicrobial Agents

  摘要：

  Dicationic 2,5-bis(4-guanidinophenyl)furans 5a-5f, 2,5-bis [4-(arylimino)aminophenyl] furans 6a -6b and 6e-6k, and 2,5-bis [4-(alkylimino)aminophenyl] furans 6c -6d have been synthesized starting from 2,5-bis [tri-n-butylstannyl] furan. Thermal melting studies with poly dA . dT and the duplex oligomer d(CGCGAATTCGCG)2 demonstrated high DNA binding affinities for a number of the compounds. The binding affinities are highly dependent on structure and are significantly affected by substituents both on the phenyl rings of the 2,5-diphenylfuran nucleus and on the cationic centers. Of the 17 novel dicationic compounds synthesized, six (6a, 6b, 5b, 6f, 6fi, 6i) exhibited MICs of 2 mug/mL or less versus Mycobacterium tuberculosis. Of the compounds screened against Candida albicans, three gave MICs of 2 mug/mL or less (5b, 6h, Si), and two (5b, 6i) were fungicidal, unlike a standard antifungal drug fluconazole, which was fungistatic. In addition, one of the tested compounds (6i) exhibited a MIC of <1 mug/mL against Aspergillus fumigatus, while also being a fungicidal against this organism. Finally, when evaluated against an expanded fungal panel, compound 6h showed good activity against Cryptococcus neoformans and Rhizopus arrhizus.

  DOI：

  10.1021/jm000413a

文献信息

• Compounds, methods and compositions useful for the treatment of bovine viral diarrhea virus (BVDV) infection and hepatitis C virus (HCV) infection
  申请人：——

  公开号：US20030199521A1

  公开（公告）日：2003-10-23

  The present invention relates to novel compounds and methods that are useful in treating members of the Flaviviridae family of viruses. Compounds of the present invention will have a structure according to Formulas (I)-(VI) as recited throughout the application.

  本发明涉及一种新型化合物和方法，可用于治疗黄病毒科病毒的成员。本发明的化合物将具有根据申请中所述的公式（I）-（VI）的结构。
• Diguanidino and “Reversed” Diamidino 2,5-Diarylfurans as Antimicrobial Agents
  作者：Chad E. Stephens、Farial Tanious、Susan Kim、W. David Wilson、Wiley A. Schell、John R. Perfect、Scott G. Franzblau、David W. Boykin

  DOI：10.1021/jm000413a

  日期：2001.5.1

  Dicationic 2,5-bis(4-guanidinophenyl)furans 5a-5f, 2,5-bis [4-(arylimino)aminophenyl] furans 6a -6b and 6e-6k, and 2,5-bis [4-(alkylimino)aminophenyl] furans 6c -6d have been synthesized starting from 2,5-bis [tri-n-butylstannyl] furan. Thermal melting studies with poly dA . dT and the duplex oligomer d(CGCGAATTCGCG)2 demonstrated high DNA binding affinities for a number of the compounds. The binding affinities are highly dependent on structure and are significantly affected by substituents both on the phenyl rings of the 2,5-diphenylfuran nucleus and on the cationic centers. Of the 17 novel dicationic compounds synthesized, six (6a, 6b, 5b, 6f, 6fi, 6i) exhibited MICs of 2 mug/mL or less versus Mycobacterium tuberculosis. Of the compounds screened against Candida albicans, three gave MICs of 2 mug/mL or less (5b, 6h, Si), and two (5b, 6i) were fungicidal, unlike a standard antifungal drug fluconazole, which was fungistatic. In addition, one of the tested compounds (6i) exhibited a MIC of <1 mug/mL against Aspergillus fumigatus, while also being a fungicidal against this organism. Finally, when evaluated against an expanded fungal panel, compound 6h showed good activity against Cryptococcus neoformans and Rhizopus arrhizus.
• The activity of diguanidino and ‘reversed’ diamidino 2,5-diarylfurans versus Trypanosoma cruzi and Leishmania donovani
  作者：Chad E. Stephens、Reto Brun、Manar M. Salem、Karl A. Werbovetz、Farial Tanious、W.David Wilson、David W. Boykin

  DOI：10.1016/s0960-894x(03)00319-6

  日期：2003.6

  The in vitro activity of 20 dicationic molecules containing either diguanidino or reversed amidine cationic groups were evaluated versus Trypanosoma cruzi and Leishmania donovani. The most active compounds were in the reversed amidine series and six exhibited IC50 values of less than 1 mumol versus T. cruzi and five gave similar values versus L. donovani. (C) 2003 Elsevier Science Ltd. All rights reserved.