2,4-bis<(4,5-dihydro-1H-imidazol-2-yl)phenyl>furan

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 2,4-bis<(4,5-dihydro-1H-imidazol-2-yl)phenyl>furan
• 英文别名: 2,4-bis[4-(2-imidazolinyl)phenyl]furan；2-[4-[4-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]furan-2-yl]phenyl]-4,5-dihydro-1H-imidazole
• 化学式: C₂₂H₂₀N₄O
• 分子量: 356.427
• InChiKey: ORXYBTZJXWABKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  61.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对氰基苯乙酮 在 盐酸 、 sodium hydroxide 、 trimethylsulfonium iodide 、 溴 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 氯仿 、 二甲基亚砜 为溶剂， 反应 101.5h， 生成 2,4-bis<(4,5-dihydro-1H-imidazol-2-yl)phenyl>furan
  参考文献：
  名称：

  2,4-Diphenyl Furan Diamidines as Novel Anti-Pneumocystis carinii Pneumonia Agents

  摘要：

  Dicationic 2,4-bis(4-amidinophenyl)furans 5-10 and 2,4-bis(4-amidinophenyl)-3,5-dimethylfurans 14 and 15 have been synthesized. Thermal melting studies revealed high binding affinity of the compounds to poly(dA-dT) and to the duplex oligomer d(CGCGAATTCGCG)(2). All of the new compounds were effective against Pneumocystis carinii pneumonia in the immunosuppressed rat model with up to 200-fold increase in activity compared to the control compound pentamidine. No toxicity was noted for 5, 7-10 at the dose of 10 mu mol/kg/d; however, the isopropyl analogue 7 showed toxicity comparable to pentamidine at the dosage of 20 mu mol/kg/d. Dimethylation of the parent compound on the furan ring resulted in reduced activity and increased toxicity.

  DOI：

  10.1021/jm990071c

文献信息

• 2,4-Bis (4-amidino)phenyl furans as anti-pneumocystis carinii agents
  申请人：UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：EP0941991A1

  公开（公告）日：1999-09-15

  Compounds according to the formula: wherein: R1 and R2 are each independently selected from the group consisting of H, loweralkyl, aryl, alkylaryl, aminoalkyl, aminoaryl, halogen, oxyalkyl, oxyaryl, or oxyarylalkyl; R3 and R4 are each independently selected from the group consisting of H, loweralkyl, oxyalkyl, alkylaryl, aryl, oxyaryl, aminoalkyl, aminoaryl, or halogen; and X and Y are located in the para or meta positions and are each selected from the group consisting of H, loweralkyl, oxyalkyl, and wherein: each R5 is independently selected from the group consisting of H, loweralkyl, alkoxyalkyl, hydroxyalkyl, aminoalkyl, alkylaminoalkyl, cycloalkyl, aryl, or alkylaryl or two R5 groups together represent C2 to C10 alkyl, hydroxyalkyl, or alkylene; and R6 is H, hydroxy, loweralkyl, alkoxyalkyl, hydroxyalkyl, aminoalkyl, alkylamino, lkylaminoalkyl, cycloalkyl, hydroxycycloalkyl, alkoxycycloalkyl, aryl, or alkylaryl; or a pharmaceutically acceptable salt thereof, are disclosed. The compounds are useful for treating Pneumocystis carinii in a subject in need of such treattment.

  符合以下式子的化合物 其中R1和R2各自独立地选自由H、低级烷基、芳基、烷芳基、氨基烷基、氨基芳基、卤素、氧基烷基、氧基芳基或氧基芳烷基组成的组；R3和R4各自独立地选自由H、低级烷基、氧基烷基、烷芳基、芳基、氧基芳基、氨基烷基、氨基芳基或卤素组成的组；以及X和Y位于对位或元位，各自选自由H、低级烷基、氧基烷基、烷芳基和卤素组成的组。 其中：每个 R5 独立地选自 H、低级烷基、烷氧基烷基、羟基烷基、氨基烷基、烷基氨基烷基、环烷基、芳基或烷基芳基组成的组，或两个 R5 基团一起代表 C2 至 C10 烷基、羟基烷基或亚烷基；以及 R6 是 H、羟基、低级烷基、烷氧基烷基、羟基烷基、氨基烷基、烷基氨基、烷基氨基烷基、环烷基、羟基环烷基、烷氧基环烷基、芳基或烷基芳基；或其药学上可接受的盐。这些化合物可用于治疗需要此类治疗的受试者的卡氏肺囊虫。
• 2,4-bis((4-Amidino)phenyl)furans as anti-pneumocystis carinii agents
  申请人：UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：EP1130019B1

  公开（公告）日：2004-05-06
• US6008247A
  申请人：——

  公开号：US6008247A

  公开（公告）日：1999-12-28
• US6127554A
  申请人：——

  公开号：US6127554A

  公开（公告）日：2000-10-03
• 2,4-Diphenyl Furan Diamidines as Novel Anti-<i>Pneumocystis carinii</i> Pneumonia Agents
  作者：Iris Francesconi、W. David Wilson、Farial A. Tanious、James E. Hall、Brendan C. Bender、Richard R. Tidwell、Donald McCurdy、David W. Boykin

  DOI：10.1021/jm990071c

  日期：1999.6.1

  Dicationic 2,4-bis(4-amidinophenyl)furans 5-10 and 2,4-bis(4-amidinophenyl)-3,5-dimethylfurans 14 and 15 have been synthesized. Thermal melting studies revealed high binding affinity of the compounds to poly(dA-dT) and to the duplex oligomer d(CGCGAATTCGCG)(2). All of the new compounds were effective against Pneumocystis carinii pneumonia in the immunosuppressed rat model with up to 200-fold increase in activity compared to the control compound pentamidine. No toxicity was noted for 5, 7-10 at the dose of 10 mu mol/kg/d; however, the isopropyl analogue 7 showed toxicity comparable to pentamidine at the dosage of 20 mu mol/kg/d. Dimethylation of the parent compound on the furan ring resulted in reduced activity and increased toxicity.