4-amino-6-(p-aminophenyl)-5-cyano-2-(p-chlorophenyl)pyrimidine | 886761-34-8

• 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-(p-chlorophenyl)pyrimidine
• 英文别名: 4-Amino-6-(4-aminophenyl)-2-(4-chlorophenyl)pyrimidine-5-carbonitrile
• CAS: 886761-34-8
• 化学式: C₁₇H₁₂ClN₅
• 分子量: 321.769
• InChiKey: OOYURHVVIIXQGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 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-(p-chlorophenyl)pyrimidine 、 苯酐 以 硝基苯 为溶剂， 反应 0.5h， 以61%的产率得到4-Amino-2-(4-chloro-phenyl)-6-[4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-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 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 9.0h， 生成 4-amino-6-(p-aminophenyl)-5-cyano-2-(p-chlorophenyl)pyrimidine
  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

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.