4-amino-2-(p-chlorophenyl)-5-cyano-6-(m-nitrophenyl)pyrimidine | 886761-30-4

• 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-2-(p-chlorophenyl)-5-cyano-6-(m-nitrophenyl)pyrimidine
• 英文别名: 4-Amino-2-(4-chlorophenyl)-6-(3-nitrophenyl)pyrimidine-5-carbonitrile
• CAS: 886761-30-4
• 化学式: C₁₇H₁₀ClN₅O₂
• 分子量: 351.752
• InChiKey: WDYMLQNRXWKYKD-UHFFFAOYSA-N

物化性质

• 熔点：
  295-296 °C(Solv: methanol (67-56-1))
• 沸点：
  515.0±50.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 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：
  121
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-amino-2-(p-chlorophenyl)-5-cyano-6-(m-nitrophenyl)pyrimidine 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 、 硝基苯 为溶剂， 反应 2.5h， 生成 4-Amino-2-(4-chloro-phenyl)-6-[3-(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：

  3-(2,2-二氰基乙烯基)-N-羟基苯胺氧化物 、 对氯苯甲脒 以 甲醇 为溶剂， 反应 7.0h， 以53%的产率得到4-amino-2-(p-chlorophenyl)-5-cyano-6-(m-nitrophenyl)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.