2,5-bis(4-amino-2,6-dimethylphenyl)furan | 347190-86-7

• 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-amino-2,6-dimethylphenyl)furan
• 英文别名: 4-[5-(4-Amino-2,6-dimethylphenyl)furan-2-yl]-3,5-dimethylaniline
• CAS: 347190-86-7
• 化学式: C₂₀H₂₂N₂O
• 分子量: 306.407
• InChiKey: BSYROZFRIFIWKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  65.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-bis(4-amino-2,6-dimethylphenyl)furan 在 盐酸 、 三乙胺 、 mercury dichloride 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 94.0h， 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 作用下， 以 1,4-二氧六环 、 乙醇 、 乙酸乙酯 为溶剂， 95.0~100.0 ℃ 、344.75 kPa 条件下， 生成 2,5-bis(4-amino-2,6-dimethylphenyl)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。
• Synthesis and antimicrobial activity of novel dicationic "reversed amidines"
  申请人：——

  公开号：US20040235927A1

  公开（公告）日：2004-11-25

  The present invention relates to novel 2,5-bis{[alkyl (or aryl) imino]aminophenyl}furans and thiophenes of the general formula 1 in which R 1 , R 2 , R 3 and R 4 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, and alkylhalide groups; R 5 is H, alkyl or aryl; R 6 is H, alkyl, aryl, or NR 7 R 8 , in which R 7 and R 8 are each independently selected from the group consisting of H, alkyl and aryl; and X is O, S or NR 9 , in which R 9 is H or alkyl, and to the use of such compounds.

  本发明涉及新型的2,5-双{[烷基（或芳基）亚胺]氨基苯基}呋喃和噻吩，其通式为1，其中R1、R2、R3和R4各自独立地选自H、烷基、烷氧基、卤素和烷基卤素基团；R5为H、烷基或芳基；R6为H、烷基、芳基或NR7R8，其中R7和R8各自独立地选自H、烷基和芳基；X为O、S或NR9，其中R9为H或烷基，并且涉及这种化合物的用途。
• Synthesis and antimicrobial activity of novel dicationic"reversed amidines"
  申请人：——

  公开号：US20030083362A1

  公开（公告）日：2003-05-01

  The present invention relates to novel 2,5-bis {[alkyl (or aryl) imino] aminophenyl} furans and thiophenes of the general formula 1 in which R 1 , R 2 , R 3 and R 4 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, and alkylhalide groups; R 5 is H, alkyl or aryl; R 6 is H, alkyl, aryl, or NR 7 R 8 , in which R 7 and R 8 are each independently selected from the group consisting of H, alkyl and aryl; and X is O, S or NR 9 , in which R 9 is H or alkyl, and to the use of such compounds.

  本发明涉及一种新型的2,5-双{[烷基（或芳基）亚胺]氨基苯基呋喃和噻吩，其通式为1，其中R1、R2、R3和R4分别独立地选自H、烷基、烷氧基、卤素和烷基卤素基团；R5为H、烷基或芳基；R6为H、烷基、芳基或NR7R8，其中R7和R8分别独立地选自H、烷基和芳基；X为O、S或NR9，其中R9为H或烷基，并且涉及这些化合物的使用。
• Reversed amidines and methods of using for treating, preventing, or inhibiting leishmaniasis
  申请人：——

  公开号：US20020156098A1

  公开（公告）日：2002-10-24

  Methods for treating, preventing or inhibiting leishmaniasis in a subject comprising administering to the subject a therapeutically effective amount of at least one compound having the structural formula 1 wherein Y is a heteroatom; R 1 and R 2 are independently H or an alkyl, cycloalkyl, heterocycloalkyl, aryl, amino or heteroaryl group; and X 1 , X 2 , and X 3 are independently H or an alkyl, alkoxy, halo, amino, alkylamino, dialkylamino, acylamino, alkylthio, sulfonyl, cyano, carboxy, alkoxycarbonyl, or carbamoyl group are disclosed.

  本发明涉及用于治疗、预防或抑制利什曼病的方法，包括向受试者施用至少一种具有结构式1的化合物的治疗有效量，其中Y是杂原子；R1和R2分别是H或烷基、环烷基、杂环烷基、芳基、氨基或杂芳基基团；X1、X2和X3分别是H或烷基、烷氧基、卤素、氨基、烷基氨基、二烷基氨基、酰胺基、烷硫基、磺酰基、氰基、羧基、烷氧羰基或氨基甲酰基基团。
• Synthesis and antimicrobial activity of novel dicationic ''reversed amidines''
  申请人：Boykin W. David

  公开号：US20080058372A1

  公开（公告）日：2008-03-06

  The present invention relates to novel 2,5-bis[alkyl(or aryl)imino]aminophenyl}furans and thiophenes of the general formula in which R 1 , R 2 , R 3 and R 4 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, and alkylhalide groups; R 5 is H, alkyl or aryl; R 6 is H, alkyl, aryl, or NR 7 R 8 , in which R 7 and R 8 are each independently selected from the group consisting of H, alkyl and aryl; and X is O, S or NR 9 , in which R 9 is H or alkyl, and to the use of such compounds.

  本发明涉及一种新型的2,5-双[烷基（或芳基）亚胺基]氨基苯基}呋喃和噻吩，其一般式如下：其中R1、R2、R3和R4各自独立地选自H、烷基、烷氧基、卤素和烷基卤素基团；R5为H、烷基或芳基；R6为H、烷基、芳基或NR7R8，其中R7和R8各自独立地选自H、烷基和芳基；X为O、S或NR9，其中R9为H或烷基，以及这些化合物的使用。