2-amino-5-(4-cyanophenyl)-furan-3-carbonitrile | 1536966-43-4

• 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: 2-amino-5-(4-cyanophenyl)-furan-3-carbonitrile
• 英文别名: 2-amino-5-(4-cyanophenyl)furan-3-carbonitrile；2-Amino-5-(4-cyanophenyl)furan-3-carbonitrile
• CAS: 1536966-43-4
• 化学式: C₁₂H₇N₃O
• 分子量: 209.207
• InChiKey: VDLZSFZTHWCMFB-UHFFFAOYSA-N

物化性质

• 沸点：
  453.5±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-5-(4-cyanophenyl)-furan-3-carbonitrile 在 甲酸 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 24.0h， 生成 (R)-4-(4-((1-phenylethyl)amino)furo[2,3-d]pyrimidin-6-yl)benzonitrile
  参考文献：
  名称：

  Chiral 6-aryl-furo[2,3-d]pyrimidin-4-amines as EGFR inhibitors

  摘要：

  Epidermal growth factor receptor inhibitors are of importance in cancer therapy and possibly in the management of pain. Herein, we report a structure-activity relationship study with 29 new 6-aryl-furo [2,3-d]pyrimidin-4-amines, involving modification of the 4-amino group and 6-aryl function. The EGFR activity was especially dependent on having a chiral 4-benzylamino group with correct stereochemistry. Molecular dynamics indicate this to be due to favourable cation-pi interactions. The most active inhibitor identified, equipotent to Erlotinib, was substituted with (R)-1-phenylethylamine at C-4 and a N-1, N-1-dimethyl-1,2-diamine group in para position of the 6-aryl moiety. These new furopyrimidines had a different off-target kinase profile when compared to Erlotinib, and also possessed high activity towards Ba/F3 EGFR(L858R) reporter cells. Further, comparing the EGFR data of the furo[2,3-d]pyrimidin-4-amines with that of the corresponding thieno- and pyrrolopyrimidines concludes the furopyrimidine scaffold to be highly useful for development of new epidermal growth factor receptor antagonists. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.04.054
• 作为产物：
  描述：

  2-溴-4'-氰基苯乙酮 在 哌啶 、 盐酸 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 4.0h， 生成 2-amino-5-(4-cyanophenyl)-furan-3-carbonitrile
  参考文献：
  名称：

  苯甲酰溴再谈：某些新的吡唑，哒嗪及其熔融衍生物的简便合成

  摘要：

  苯甲酰基丙二腈8a，8b在干燥条件下与肼反应，得到吡唑衍生物9a，9b，9c，9d，在回流的二恶烷中，得到吡唑并[3,4- c ]哒嗪衍生物11a，11b，11c，11d和哒嗪- 6-亚胺衍生物12a，12b，12c，12d。将化合物12a，12b转化为其氧代类似物13a，13b在乙醇HCl中回流时，而12c，12d在相同反应条件下（在乙醇HCl中回流）转化为呋喃衍生物14a，14b。与吡啶中的重氮化芳族胺偶联后，化合物8a，8b可直接转化为苯甲酰基-吡唑衍生物16a，16b，16c，16d。新化合物的结构通过元素分析和光谱数据以及X射线晶体学分析得到证实。建议用于意外转换的合理机制。

  DOI：

  10.1002/jhet.1664

文献信息

• Phenacyl Bromides Revisited: Facile Synthesis of Some New Pyrazoles, Pyridazines, and Their Fused Derivatives
  作者：Fathy M. Abdelrazek、Hamdi M. Hassaneen、Ekhlass M. Nassar、Anna Jager

  DOI：10.1002/jhet.1664

  日期：2014.3

  Phenacylmalononitriles 8a, 8b react with hydrazines under dry conditions to afford the pyrazole derivatives 9a, 9b, 9c, 9d and in refluxing dioxane to afford the pyrazolo[3,4‐c]pyridazine derivatives 11a, 11b, 11c, 11d and the pyridazine‐6‐imine derivatives 12a, 12b, 12c, 12d. Compounds 12a, 12b were transformed into their oxo analogs 13a, 13b upon reflux in ethanolic HCl, whereas 12c, 12d were transformed

  苯甲酰基丙二腈8a，8b在干燥条件下与肼反应，得到吡唑衍生物9a，9b，9c，9d，在回流的二恶烷中，得到吡唑并[3,4- c ]哒嗪衍生物11a，11b，11c，11d和哒嗪- 6-亚胺衍生物12a，12b，12c，12d。将化合物12a，12b转化为其氧代类似物13a，13b在乙醇HCl中回流时，而12c，12d在相同反应条件下（在乙醇HCl中回流）转化为呋喃衍生物14a，14b。与吡啶中的重氮化芳族胺偶联后，化合物8a，8b可直接转化为苯甲酰基-吡唑衍生物16a，16b，16c，16d。新化合物的结构通过元素分析和光谱数据以及X射线晶体学分析得到证实。建议用于意外转换的合理机制。
• Chiral 6-aryl-furo[2,3-d]pyrimidin-4-amines as EGFR inhibitors
  作者：Jin Han、Svein Jacob Kaspersen、Sondre Nervik、Kristin G. Nørsett、Eirik Sundby、Bård Helge Hoff

  DOI：10.1016/j.ejmech.2016.04.054

  日期：2016.8

  Epidermal growth factor receptor inhibitors are of importance in cancer therapy and possibly in the management of pain. Herein, we report a structure-activity relationship study with 29 new 6-aryl-furo [2,3-d]pyrimidin-4-amines, involving modification of the 4-amino group and 6-aryl function. The EGFR activity was especially dependent on having a chiral 4-benzylamino group with correct stereochemistry. Molecular dynamics indicate this to be due to favourable cation-pi interactions. The most active inhibitor identified, equipotent to Erlotinib, was substituted with (R)-1-phenylethylamine at C-4 and a N-1, N-1-dimethyl-1,2-diamine group in para position of the 6-aryl moiety. These new furopyrimidines had a different off-target kinase profile when compared to Erlotinib, and also possessed high activity towards Ba/F3 EGFR(L858R) reporter cells. Further, comparing the EGFR data of the furo[2,3-d]pyrimidin-4-amines with that of the corresponding thieno- and pyrrolopyrimidines concludes the furopyrimidine scaffold to be highly useful for development of new epidermal growth factor receptor antagonists. (C) 2016 Elsevier Masson SAS. All rights reserved.