2,5-bis(2,6-dimethyl-4-N,N'-di-BOCguanidinophenyl)furan | 347190-92-5

• 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(2,6-dimethyl-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]-2,6-dimethylphenyl]furan-2-yl]-3,5-dimethylanilino]-[(2-methylpropan-2-yl)oxycarbonylamino]methylidene]carbamate
• CAS: 347190-92-5
• 化学式: C₄₂H₅₈N₆O₉
• 分子量: 790.957
• InChiKey: MMFBMVVGTGGKHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 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(2,6-dimethyl-4-N,N'-di-BOCguanidinophenyl)furan 在 盐酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 2,5-bis(4-guanidino-2,6-dimethylphenyl)furan dihydrochloride
  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
• 作为产物：
  描述：

  2-溴-1,3-二甲基-5-硝基苯 在 10percent Pd/C 四(三苯基膦)钯 、 氢气 、 三乙胺 、 mercury dichloride 作用下， 以 1,4-二氧六环 、 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0~100.0 ℃ 、344.75 kPa 条件下， 反应 22.0h， 生成 2,5-bis(2,6-dimethyl-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

• 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.