2-(4-(5-(4-cyanophenoxy)pentyloxy)phenyl)benzofuran-6-carbonitrile | 854895-39-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2-(4-(5-(4-cyanophenoxy)pentyloxy)phenyl)benzofuran-6-carbonitrile
• 英文别名: 2-[4-[5-(4-Cyanophenoxy)pentoxy]phenyl]-1-benzofuran-6-carbonitrile
• CAS: 854895-39-9
• 化学式: C₂₇H₂₂N₂O₃
• 分子量: 422.483
• InChiKey: CHXBGVQKMWONET-UHFFFAOYSA-N

物化性质

• 熔点：
  165-167 °C(Solv: N,N-dimethylformamide (68-12-2); ethanol (64-17-5))
• 沸点：
  653.7±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  79.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙醇 、 2-(4-(5-(4-cyanophenoxy)pentyloxy)phenyl)benzofuran-6-carbonitrile 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 C₃₁H₃₄N₂O₅*2ClH
  参考文献：
  名称：

  Synthesis and Antiprotozoal Properties of Pentamidine Congeners Bearing the Benzofuran Motif

  摘要：

  Forty-eight cationically substituted pentamidine Congeners possessing benzofuran rings were synthesized by a copper mediated heteroannulation of substituted o-iodophenols with phenyl acetylenes. Activities of compounds 1-48 against Trypanosoma brucei rhodesiense, Plasmodium falciparum, and Leishmania donovani and cytotoxicities for mammalian cells were influenced by the nature of cationic substituents, placement of the benzofuran fragment, and the length of the carbon linker between aromatic moieties. Several dications exhibited superior antiplasmodial and antileishmanial potencies compared to pentamidine.

  DOI：

  10.1021/jm9006406
• 作为产物：
  描述：

  2-(4-hydroxyphenyl)benzofuran-6-carbonitrile 、 4-[(5-bromopentyl)oxy]benzonitrile 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到2-(4-(5-(4-cyanophenoxy)pentyloxy)phenyl)benzofuran-6-carbonitrile
  参考文献：
  名称：

  Synthesis and Antiprotozoal Properties of Pentamidine Congeners Bearing the Benzofuran Motif

  摘要：

  Forty-eight cationically substituted pentamidine Congeners possessing benzofuran rings were synthesized by a copper mediated heteroannulation of substituted o-iodophenols with phenyl acetylenes. Activities of compounds 1-48 against Trypanosoma brucei rhodesiense, Plasmodium falciparum, and Leishmania donovani and cytotoxicities for mammalian cells were influenced by the nature of cationic substituents, placement of the benzofuran fragment, and the length of the carbon linker between aromatic moieties. Several dications exhibited superior antiplasmodial and antileishmanial potencies compared to pentamidine.

  DOI：

  10.1021/jm9006406

文献信息

• Cationic substituted benzofurans as antimicrobial agents
  申请人：Tidwell R. Richard

  公开号：US20050197378A1

  公开（公告）日：2005-09-08

  A method of treating a Mycobacterium tuberculosis infection in a subject in need thereof by administering to the subject an effective amount of a cationic substituted benzofuran compound. Methods of treating microbial infections, including infections from protozoan pathogens, such as Leishmania donovani, Trypanosoma brucei rhodesiense , a Trypanosoma cruzi , and Plasmodium falciparum , and fungal pathogens, such as Candida albicans, Aspergillus fumigatus , and Cryptococcus neoformans , in a subject in need thereof by administering to the subject an effective amount of a cationic substituted benzofuran compound. Methods of synthesizing novel cationic substituted benzofuran compounds and the novel compounds themselves.

  本发明涉及一种治疗需要治疗的主体中的结核分枝杆菌感染的方法，包括向该主体内给予阳离子取代苯并呋喃化合物的有效量。本发明还涉及治疗微生物感染的方法，包括来自原虫病原体的感染，例如Leishmania donovani，Trypanosoma brucei rhodesiense，Trypanosoma cruzi和Plasmodium falciparum，以及真菌病原体，例如Candida albicans，Aspergillus fumigatus和Cryptococcus neoformans，包括向需要治疗的主体内给予阳离子取代苯并呋喃化合物的有效量。本发明还涉及合成新的阳离子取代苯并呋喃化合物的方法以及这些新化合物本身。
• CATIONIC SUBSTITUTED BENZOFURANS AS ANTIMICROBIAL AGENTS
  申请人：THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：EP1689732A2

  公开（公告）日：2006-08-16
• EP1689732A4
  申请人：——

  公开号：EP1689732A4

  公开（公告）日：2008-10-22
• US7417158B2
  申请人：——

  公开号：US7417158B2

  公开（公告）日：2008-08-26
• [EN] CATIONIC SUBSTITUTED BENZOFURANS AS ANTIMICROBIAL AGENTS<br/>[FR] BENZOFURANES SUBSTITUES CATIONIQUES UTILES EN TANT QU'AGENTS ANTIMICROBIENS
  申请人：UNIV NORTH CAROLINA

  公开号：WO2005055935A2

  公开（公告）日：2005-06-23

  A method of treating a Myobacterium tuberculosis infection in a subject in need thereof by administering to the subject an effective amount of a cationic substituted benzofuran compound. Methods of treating microbial infections, including infections from protozoan pathogens, such as Leishmania donovani, Trypanosoma brucei rhodesiense, a Trypanosoma cruzi, and Plasmodium falciparum, and fungal pathogens, such as Candida albicans, Aspergillus fumigatus, and Cryptococcus neoformans, in a subject in need thereof by administering to the subject an effective amount of a cationic substituted benzofuran compound. Methods of synthesizing novel cationic substituted benzofuran compounds and the novel compounds themselves.