5-amino-1-(4-methoxyphenyl)-1H-imidazole-4-carbonitrile | 155579-43-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-amino-1-(4-methoxyphenyl)-1H-imidazole-4-carbonitrile
• 英文别名: 5-amino-4-nitrile-1-p-methoxyphenyl-imidazole；5-amino-1-(4-methoxyphenyl)-4-cyanoimidazole；5-amino-1-(4-methoxyphenyl)imidazole-4-carbonitrile
• CAS: 155579-43-4
• 化学式: C₁₁H₁₀N₄O
• 分子量: 214.227
• InChiKey: OXQWYPZAYYCJMG-UHFFFAOYSA-N

物化性质

• 熔点：
  171-172.5 °C (decomp)(Solv: ethanol (64-17-5); methanol (67-56-1))
• 沸点：
  471.0±40.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  76.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-amino-1-(4-methoxyphenyl)-1H-imidazole-4-carbonitrile 在 lithium triethoxyaluminum hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以67%的产率得到5-Amino-1-(4-methoxy-phenyl)-1H-imidazole-4-carbaldehyde
  参考文献：
  名称：

  Synthesis of 1-Substituted 5-Aminoimidazole-4-carbaldehydes and 8-Amino-1-(2-fluorobenzyl)imidazo[4’,5’:5,6]pyrido[2,3-d]pyrimidine

  摘要：

  报道了通过还原相应的5-氨基-4-氰基咪唑衍生物，合成多种1-取代的5-氨基咪唑-4-醛（3），该还原反应使用了由LiAlH4和乙酸乙酯原位制备的LiAlH(OEt)3。类型1的化合物是合成延伸腺苷衍生物的有用中间体。

  DOI：

  10.1055/s-2001-18705
• 作为产物：
  描述：

  N¹-(4-methoxyphenyl)-N²-(Z)-[2-amino-1,2-dicyanovinyl]formamidine 在 氢氧化钾 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 为溶剂， 生成 5-amino-1-(4-methoxyphenyl)-1H-imidazole-4-carbonitrile
  参考文献：
  名称：

  Synthesis of 5-Amino-4-cyanoformimidoylimidazoles and 5-Amino-4-cyanoimidazoles from Amidines

  摘要：

  Imidazole and formimidoylimidazole derivatives have been synthesized in high yields by a reaction between amidine and a strong or weak base depending on reaction conditions and mainly on the nature of the base used to induced cyclization. All compounds have been characterized by spectroscopic data.

  DOI：

  10.1080/10426500500326982

文献信息

• New application of heterocyclic diazonium salts. Synthesis of pyrazolo[3,4-d][1,2,3]triazin-4-ones and imidazo[4,5-d][1,2,3]triazin-4-ones
  作者：Juan Pablo Colomer、Elizabeth Laura Moyano

  DOI：10.1016/j.tetlet.2011.01.040

  日期：2011.4

  The pyrazolo[3,4-d][1,2,3]triazin-4-ones 3 and imidazo[4,5-d][1,2,3]triazin-4-ones 4 are analogs structurally related to purines that have showed a wide and significant variety of biological activity. These compounds were synthesized by one-pot diazotization of 5-amino-1H-pyrazole-4-carbonitriles 1 and 5-amino-1H-imidazole-4-carbonitriles 2, respectively.

  吡唑并[3,4- d ] [1,2,3] triazin-4-ones 3和咪唑并[4,5- d ] [1,2,3] triazin-4-ones 4是与嘌呤在结构上相关的类似物表现出广泛而显着的生物活性。这些化合物分别通过一锅重氮化5-氨基-1 H-吡唑-4-腈1和5-氨基-1 H-咪唑-4-腈2合成。
• Adenine Derivatives: Promising Candidates for Breast Cancer Treatment
  作者：Pedro Figueiredo、Marta Costa、Olívia Pontes、Fátima Baltazar、Fernanda Proença

  DOI：10.1002/ejoc.201800629

  日期：2018.8.7

  We acknowledge the financial support from University of Minho, Fundacao para a Ciencia e a Tecnologia (FCT) and FEDER-COMPETE through Centro de Quimica (UID/QUI/00686/ 2013 and UID/QUI/0686/2016). The NMR spectrometer Bruker Avance III 400 is part of the National NMR Network (RNRMN) and was purchased within the framework of the National Program for Scientific Re-equipment, contract REDE/1517/RMN/ 2005

  我们感谢 Minho 大学、Fundacao para a Ciencia ea Tecnologia (FCT) 和 FEDER-COMPETE 通过 Centro de Quimica (UID/QUI/00686/2013 和 UID/QUI/0686/2016) 的财政支持。NMR 波谱仪 Bruker Avance III 400 是国家核磁共振网络 (RNRMN) 的一部分，是在国家科学再设备计划框架内购买的，合同 REDE/1517/RMN/2005，资金来自 POCI 2010 (FEDER) 和FCT。这项工作也是在 NORTE-01-0145-FEDER-000013 项目的范围内开发的，由葡萄牙伙伴关系协议下的北葡萄牙区域运营计划 (NORTE 2020) 通过欧洲区域发展基金 (FEDER) 提供支持，以及通过竞争力因素运营计划 (COMPETE) 和国家基金，通过
• New chromene scaffolds for adenosine A2A receptors: Synthesis, pharmacology and structure–activity relationships
  作者：Filipe Areias、Marta Costa、Marián Castro、José Brea、Elisabet Gregori-Puigjané、M. Fernanda Proença、Jordi Mestres、María I. Loza

  DOI：10.1016/j.ejmech.2012.05.009

  日期：2012.8

  In silico screening of a c ollection of 1584 academic compounds identified a small molecule hit for the human adenosine A(2A) receptor (pK(i) = 6.2) containing a novel chromene scaffold (3a). To explore the structure activity relationships of this new chemical series for adenosine receptors, a focused library of 43 2H-chromene-3-carboxamide derivatives was synthesized and tested in radioligand binding assays at human adenosine A(1), A(2A), A(2B) and A(3) receptors. The series was found to be enriched with bioactive compounds for adenosine receptors, with 14 molecules showing submicromolar affinity (pK(i) >= 6.0) for at least one adenosine receptor subtype. These results provide evidence that the chromene scaffold, a core structure present in natural products from a wide variety of plants, vegetables, and fruits, constitutes a valuable source for novel therapeutic agents. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis and radical scavenging activity of phenol–imidazole conjugates
  作者：Carla Correia、Cláudia Leite、M. Fernanda Proença、M. Alice Carvalho

  DOI：10.1016/j.bmcl.2014.04.026

  日期：2014.6

  Novel hydroxylated benzylideneamino imidazole derivatives were synthesized and their radical scavenging activity was assessed against DPPH and hydroxyl radicals. In the DPPH assay, most of the synthesized compounds showed an IC50 in the range 3.2 mu M <= IC50 <= 8.4 mu M, lower than the reference compound trolox (IC50 = 9.5 mu M) or the parent aldehydes (5.4 mu M <= IC50 <= 11.6 mu M). The activity depends mainly on the phenolic subunit (number and position of the hydroxyl groups) and the extent of conjugation with the imidazole ring. In the deoxyribose assay, all the compounds, including parent imidazoles and aldehydes, showed high activity against the hydroxyl radical and the ability to chelate iron ions. At 5 mu M concentration, the compounds protected the deoxyribose from degradation by hydroxyl radical between 62% and 38%. (C) 2014 Elsevier Ltd. All rights reserved.
• Alves, M. Jose; Booth, Brian L; Al-Duaij, Omar Kh., Journal of Chemical Research, Miniprint, 1993, # 10, p. 2701 - 2719
  作者：Alves, M. Jose、Booth, Brian L、Al-Duaij, Omar Kh.、Eastwood, Paul、Nezhat, Lida、et al.

  DOI：——

  日期：——