N'-(2-amino-1,2-dicyanovinyl)-N-(4-fluorophenyl)formimidamide | 499983-03-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N'-(2-amino-1,2-dicyanovinyl)-N-(4-fluorophenyl)formimidamide
• CAS: 499983-03-8
• 化学式: C₁₁H₈FN₅
• 分子量: 229.216
• InChiKey: CGXZMFJUBJNQDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.99
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N'-(2-amino-1,2-dicyanovinyl)-N-(4-fluorophenyl)formimidamide 在 水 、 三氟乙酸 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 5-[(3,4-Dihydroxyphenyl)methylideneamino]-1-(4-fluorophenyl)imidazole-4-carbonitrile
  参考文献：
  名称：

  Synthesis and radical scavenging activity of phenol–imidazole conjugates

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2014.04.026
• 作为产物：
  描述：

  N-(2-amino-1,2-dicyano-vinyl)-formimydic acid ethyl ester 、 4-氟苯胺 以 乙醇 为溶剂， 生成 N'-(2-amino-1,2-dicyanovinyl)-N-(4-fluorophenyl)formimidamide
  参考文献：
  名称：

  Synthesis and radical scavenging activity of phenol–imidazole conjugates

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2014.04.026

文献信息

• Anticancer potential of some imidazole and fused imidazole derivatives: exploring the mechanism <i>via</i> epidermal growth factor receptor (EGFR) inhibition
  作者：Sourav Kalra、Gaurav Joshi、Manvendra Kumar、Sahil Arora、Harsimrat Kaur、Sandeep Singh、Anjana Munshi、Raj Kumar

  DOI：10.1039/d0md00146e

  日期：——

  Imidazole-based epidermal growth factor receptor (EGFR) inhibitors were computationally designed and synthesized. All the compounds were assessed for their anti-proliferative activity against five cancer cell lines, viz., MDA-MB-231 (breast), T47D (breast) and MCF-7 (breast), A549 (lung) and HT-29 (colorectal). Compounds 2c and 2d emerged as better anticancer molecules with no toxicity towards normal

  基于咪唑的表皮生长因子受体 (EGFR) 抑制剂是通过计算设计和合成的。评估了所有化合物对五种癌细胞系的抗增殖活性，即。、MDA-MB-231（乳房）、T47D（乳房）和 MCF-7（乳房）、A549（肺）和 HT-29（结肠直肠）。化合物2c和2d成为更好的抗癌分子，对正常细胞没有毒性。2c和2d在体外抑制EGFR酶活性，IC 50值分别为617.33 ± 0.04 nM和710 ± 0.05 nM。为了进一步提高效力，我们探索了EGFR的ATP结合域的一个未被占用的区域并对其进行了分析2c和2d -EGFR 配合物的计算机相互作用模型，该模型引导并允许在 N-9 位置用 4-(4-甲基哌嗪基)-3-硝基苯基取代 4-氟苯基环（2c和2d ），得到化合物3c具有更好的结合评分和有效的 EGFR 抑制活性 (IC 50 : 236.38 ± 0.04 nM)，与阳性对照厄洛替尼 (239.91
• 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