ethyl 4-[5-[4-(C-ethoxycarbonimidoyl)phenyl]furan-2-yl]benzenecarboximidate | 236098-07-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: ethyl 4-[5-[4-(C-ethoxycarbonimidoyl)phenyl]furan-2-yl]benzenecarboximidate
• CAS: 236098-07-0
• 化学式: C₂₂H₂₂N₂O₃
• 分子量: 362.428
• InChiKey: BFDYPXGCALRVHN-UHFFFAOYSA-N

物化性质

• 沸点：
  452.8±55.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  79.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3-氨基丙基)吡咯烷 、 ethyl 4-[5-[4-(C-ethoxycarbonimidoyl)phenyl]furan-2-yl]benzenecarboximidate 以 乙醇 为溶剂， 反应 24.0h， 生成 2,5-bis[4-[N-(3-(N-pyrrolidino)propyl)amidino]phenyl]furan
  参考文献：
  名称：

  Inhibition of the HIV-1 rev–RRE complex formation by unfused aromatic cations

  摘要：

  RNA viruses cause a wide range of human diseases. Development of new agents to target such viruses is an active area of research. Towards this goal, a series of diphenylfuran cations as potential inhibitors of the Rev-RRE complex have been designed and synthesized. Analysis of the interaction of the diphenylfurans with RRE and TAR RNA model systems by gel shift assays indicates that they exhibit both sequence and structure-dependent binding modes. Our results show a strong interaction between the diphenylfuran ring system and RRE bases, while the TAR interactions are much weaker with the compounds that are the best inhibitors of Rev-RRE. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00344-8
• 作为产物：
  描述：

  4,4'-(2,5-呋喃二基)二-苯甲腈 、 乙醇 反应 168.0h， 以90%的产率得到ethyl 4-[5-[4-(C-ethoxycarbonimidoyl)phenyl]furan-2-yl]benzenecarboximidate
  参考文献：
  名称：

  2,5-Bis[4-(N-alkylamidino)phenyl]furans as Anti-Pneumocystis carinii Agents

  摘要：

  The syntheses of 12 new 2,5-bis[4-(N-alkylamidino)phenyl]furans are reported. The interaction of these dicationic furans with poly(dA-dT) and with the duplex oligomer d(CGCGAATTCGCG)(2) was determined by T-m measurements, and the effectiveness of these compounds against the immunosuppressed rat model of Pneumocystis carinii was evaluated. At the screening dose of 10 mu mol/kg, 9 of the 14 N-alkylamidino furans described here are more active than the parent compound 1. Substitution of an alkyl group on the amidino nitrogen, except for in 9, 13, and 15, resulted in higher affinity for DNA than the parent compound as judged by the larger Delta T-m values and suggests enhanced van der Waals interact ions in the bis-amidine-DNA complex. Five of the compounds, 3, 5, 7, 10, and 12, yield cyst counts of less than 0.1% of control when administered at a dosage of 10 mu mol/kg. Five compounds, 1, 6, 8, 10, and 12, show significant activity at a dosage of approximately 1 mu mol/kg; 12 is the most active derivative, and it is approximately 100 times more effective than pentamidine in this animal model.

  DOI：

  10.1021/jm970570i

文献信息

• Targeting the Minor Groove of DNA:  Crystal Structures of Two Complexes between Furan Derivatives of Berenil and the DNA Dodecamer d(CGCGAATTCGCG)₂
  作者：John O. Trent、George R. Clark、Arvind Kumar、W. David Wilson、David W. Boykin、James Edwin Hall、Richard R. Tidwell、Byron L. Blagburn、Stephen Neidle

  DOI：10.1021/jm9604484

  日期：1996.1.1

  isopropyl-substituted derivative has a tight hydrogen-bonded water network in the minor groove at one amidine site, which alters the orientation of the isopropyl substituent. This compound has superior DNA-binding properties and activity against Pneumocystis carinii and Cryptosporidium parvum infections in vivo compared to the cyclopropyl derivative, which in turn is superior to the parent furan compound

  据报道晶体结构的苯酚的两个新型呋喃衍生物与烷基苯甲am基团绑定到DNA序列d（CGCGAATTCGCG）2的配合物。它们均被确定为2.2 A分辨率，并已精炼为16.9％和18.6％的R因子。在这两个结构中，发现烷基取代基环丙基和异丙基的取向远离小凹槽的底部。药物通过两个强am基氢键位于次要凹槽中，位于富AT区5'和3'端的胸腺嘧啶的O2上。异丙基取代的衍生物在一个idine位的小槽中具有紧密的氢键水网络，从而改变了异丙基取代基的方向。与环丙基衍生物相比，该化合物具有优异的DNA结合特性，并且在体内具有抗卡氏肺孢子虫和小隐孢子虫感染的活性，而环丙基衍生物又优于母体呋喃化合物。我们建议这些化合物在DNA小沟中相互作用的性质和程度在这些活动中可能起重要作用，可能与DNA结合蛋白结合在一起。这些烷基苯甲idine取代的总体作用是增加药物与小沟的结合。可能与DNA结合蛋白结合使用。这些烷基苯甲idi
• 2,5-Bis[4-(<i>N</i>-alkylamidino)phenyl]furans as Anti-<i>Pneumocystis carinii</i> Agents
  作者：David W. Boykin、Arvind Kumar、Ge Xiao、W. David Wilson、Brendan C. Bender、Donald R. McCurdy、James Edwin Hall、Richard R. Tidwell

  DOI：10.1021/jm970570i

  日期：1998.1.1

  The syntheses of 12 new 2,5-bis[4-(N-alkylamidino)phenyl]furans are reported. The interaction of these dicationic furans with poly(dA-dT) and with the duplex oligomer d(CGCGAATTCGCG)(2) was determined by T-m measurements, and the effectiveness of these compounds against the immunosuppressed rat model of Pneumocystis carinii was evaluated. At the screening dose of 10 mu mol/kg, 9 of the 14 N-alkylamidino furans described here are more active than the parent compound 1. Substitution of an alkyl group on the amidino nitrogen, except for in 9, 13, and 15, resulted in higher affinity for DNA than the parent compound as judged by the larger Delta T-m values and suggests enhanced van der Waals interact ions in the bis-amidine-DNA complex. Five of the compounds, 3, 5, 7, 10, and 12, yield cyst counts of less than 0.1% of control when administered at a dosage of 10 mu mol/kg. Five compounds, 1, 6, 8, 10, and 12, show significant activity at a dosage of approximately 1 mu mol/kg; 12 is the most active derivative, and it is approximately 100 times more effective than pentamidine in this animal model.
• Inhibition of the HIV-1 rev–RRE complex formation by unfused aromatic cations
  作者：G Xiao

  DOI：10.1016/s0968-0896(00)00344-8

  日期：2001.5

  RNA viruses cause a wide range of human diseases. Development of new agents to target such viruses is an active area of research. Towards this goal, a series of diphenylfuran cations as potential inhibitors of the Rev-RRE complex have been designed and synthesized. Analysis of the interaction of the diphenylfurans with RRE and TAR RNA model systems by gel shift assays indicates that they exhibit both sequence and structure-dependent binding modes. Our results show a strong interaction between the diphenylfuran ring system and RRE bases, while the TAR interactions are much weaker with the compounds that are the best inhibitors of Rev-RRE. (C) 2001 Elsevier Science Ltd. All rights reserved.