4-amino-6-(p-aminophenyl)-5-cyano-2-phenylpyrimidine | 886761-33-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-amino-6-(p-aminophenyl)-5-cyano-2-phenylpyrimidine
• 英文别名: 4-Amino-6-(4-aminophenyl)-2-phenylpyrimidine-5-carbonitrile
• CAS: 886761-33-7
• 化学式: C₁₇H₁₃N₅
• 分子量: 287.324
• InChiKey: FEFDNHMUZPIDQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-6-(p-aminophenyl)-5-cyano-2-phenylpyrimidine 、 苯酐 以 硝基苯 为溶剂， 反应 0.5h， 以64%的产率得到4-Amino-6-[4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-phenyl]-2-phenyl-pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Synthesis and antiinflammatory activity of 4-amino-2-aryl-5-cyano-6-{3- and 4-(N-phthalimidophenyl)} pyrimidines

  摘要：

  Six new 4-amino-5-eyano-2,6-diarylpyrimidines 5a-h has been synthesized in a facile manner by reacting the appropriate arylamidines 4a-d with bisnitriles 3a-e. Reduction of the nitro group of 5a-e using Pd in ethyl acetate furnished 6a-e in good yields. Reaction of 6a-e individually with phthalic anhydride yielded 7a-e in good to excellent yields. The newly synthesized heterocycles were characterized by IR, H-1-NMR and mass spectral data. Compounds 5f-h and 7a-e were also evaluated against inflammation. Pyrimidines 5g, h exhibited better anti inflammatory activity when compared with acetylsalicylic acid (ASA). Phthalimide derivatives 7a-e also presented antiinflammatory activity, and three of them, viz., 7a-c have been found to be twice more active than aspirin. Cytotoxical evaluations of compounds 7a-e using neoplastic cells (NCI-H-292 and Hep-2) presented 41% of growth inhibition of neoplastic cells NCI-H-292. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.09.009
• 作为产物：
  描述：

  1,1-二氰基-2-(-p-硝基苯基)-乙烯 在 哌啶 、 palladium on carbon 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 6.0h， 生成 4-amino-6-(p-aminophenyl)-5-cyano-2-phenylpyrimidine
  参考文献：
  名称：

  嘧啶衍生物的合成，抗胰酶活性和分子对接研究

  摘要：

  该出版物描述了28种嘧啶衍生物的合成，其中8种是新的。其结构已通过光谱技术（IR，H1，C13 NMR数据）验证。质谱分析正确给出了所有化合物的元素组成。已针对克鲁氏锥虫的两个不同阶段对所有28种化合物进行了体外评估：1.副鞭毛虫和2.鞭毛鞭毛虫。化合物3a，3b，3j，3k，3o，3s和5d表现出比苯并硝唑（BZN）更大的活性。化合物3a的选择性类似于BZN。使用对接方法进行分子建模以确定配体与酶的结合。使用GOLD 5.2程序进行的MO计算提供了有关该酶与嘧啶结合位点的信息。

  DOI：

  10.1007/s00044-018-2253-2

文献信息

• Synthesis and antiinflammatory activity of 4-amino-2-aryl-5-cyano-6-{3- and 4-(N-phthalimidophenyl)} pyrimidines
  作者：Emerson Peter da S. Falcão、Sebastião J. de Melo、Rajendra M. Srivastava、Maria Tereza Jansen de A. Catanho、Silene Carneiro Do Nascimento

  DOI：10.1016/j.ejmech.2005.09.009

  日期：2006.2

  Six new 4-amino-5-eyano-2,6-diarylpyrimidines 5a-h has been synthesized in a facile manner by reacting the appropriate arylamidines 4a-d with bisnitriles 3a-e. Reduction of the nitro group of 5a-e using Pd in ethyl acetate furnished 6a-e in good yields. Reaction of 6a-e individually with phthalic anhydride yielded 7a-e in good to excellent yields. The newly synthesized heterocycles were characterized by IR, H-1-NMR and mass spectral data. Compounds 5f-h and 7a-e were also evaluated against inflammation. Pyrimidines 5g, h exhibited better anti inflammatory activity when compared with acetylsalicylic acid (ASA). Phthalimide derivatives 7a-e also presented antiinflammatory activity, and three of them, viz., 7a-c have been found to be twice more active than aspirin. Cytotoxical evaluations of compounds 7a-e using neoplastic cells (NCI-H-292 and Hep-2) presented 41% of growth inhibition of neoplastic cells NCI-H-292. (c) 2006 Elsevier SAS. All rights reserved.
• Synthesis, antitrypanosomal activity and molecular docking studies of pyrimidine derivatives
  作者：Sebastião José de Melo、Zenaide Severina do Monte、Aline Caroline da Silva Santos、Ana Catarina Cristovão Silva、Luiz Felipe Gomes Rebello Ferreira、Marcelo Zaldini Hernandes、Ricardo Oliveira Silva、Emerson Peter da Silva Falcão、Maria Carolina Accioly Brelaz-de-Castro、Rajendra M. Srivastava、Valeria Rêgo Alves Pereira

  DOI：10.1007/s00044-018-2253-2

  日期：2018.12

  trypomastigotes. Compounds 3a, 3b, 3j, 3k, 3o, 3s and 5d presented greater activity than benznidazole(BZN) for trypomastigotes. Compound 3a selectivity was similar to that of BZN. Molecular modeling using the Docking approach was performed to determine binding of the ligand to the enzyme. The M.O. calculations using the GOLD 5.2 program provided information on the pyrimidine binding sites with the enzyme.

  该出版物描述了28种嘧啶衍生物的合成，其中8种是新的。其结构已通过光谱技术（IR，H1，C13 NMR数据）验证。质谱分析正确给出了所有化合物的元素组成。已针对克鲁氏锥虫的两个不同阶段对所有28种化合物进行了体外评估：1.副鞭毛虫和2.鞭毛鞭毛虫。化合物3a，3b，3j，3k，3o，3s和5d表现出比苯并硝唑（BZN）更大的活性。化合物3a的选择性类似于BZN。使用对接方法进行分子建模以确定配体与酶的结合。使用GOLD 5.2程序进行的MO计算提供了有关该酶与嘧啶结合位点的信息。