4-amino-5-(4-chloro-phenylazo)-6-dibenzylamino-1-methyl-pyrimidin-2-one

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-amino-5-(4-chloro-phenylazo)-6-dibenzylamino-1-methyl-pyrimidin-2-one
• 英文别名: 4-amino-5-[(E)-(4-chlorophenyl)azo]-6-(dibenzylamino)-1-methyl-pyrimidin-2-one；4-amino-5-[(4-chlorophenyl)diazenyl]-6-(dibenzylamino)-1-methylpyrimidin-2-one
• 化学式: C₂₅H₂₃ClN₆O
• 分子量: 458.95
• InChiKey: YXCONKWXOCBBBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  86.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-amino-5-(4-chloro-phenylazo)-6-dibenzylamino-1-methyl-pyrimidin-2-one 、 3,4-二甲氧基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 丙醇 、 水 为溶剂， 反应 12.0h， 以65%的产率得到4-amino-6-(dibenzylamino)-5-((3',4'-dimethoxy-[1,1'-biphenyl]-4-yl)diazenyl)-1-methylpyrimidin-2-one
  参考文献：
  名称：

  Synthesis of Potential Pyrimidine Derivatives via Suzuki Cross-Coupling Reaction as HIV and Kinesin Eg5 Inhibitors

  摘要：

  A series of 4-amino-5-((4-chlorophenyl)diazenyl)-6-(alkylamino)-1-methylpyrimidin-2-one deri- vatives 7-16 were prepared by nucleophilic displacement of 6-chloro-pyrimidine 6 by various amines. 4-Amino-5-((aryl-4-yl)diazenyl)-6-aryl-1-methylpyrimidin-2-one analogs 19-27, as well as 4-amino-5-((aryl-[1,1 '-biphenyl]-4-yl)diazenyl)-6-aryl-1-methylpyrimidin-2-one 29-31 and 4-amino-6-aryl-1-methylpyrimidin-2-one 34-34, were synthesized via Suzuki cross-coupling reaction, using Pd(PPh3)(4) as a catalyst and arylboronic acids as reagents. All compounds were evaluated for their antiviral activity against the replication of HIV-1 and HIV-2 in MT-4. Compounds 6, 16, 27, and 29 showed a 50% effective concentration of >2.15, >3.03, >2.29, and >1.63 mu M, respectively, but no selectivity was observed (selectivity index < 1). Two of the newly synthesized pyrimidines 12 and 29 exhibited moderate kinesin Eg5 inhibition.

  DOI：

  10.1080/15257770.2014.880475
• 作为产物：
  描述：

  4-amino-6-chloro-1-methylpyrimidin-2-one 在 盐酸 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.5h， 生成 4-amino-5-(4-chloro-phenylazo)-6-dibenzylamino-1-methyl-pyrimidin-2-one
  参考文献：
  名称：

  Synthesis of Potential Pyrimidine Derivatives via Suzuki Cross-Coupling Reaction as HIV and Kinesin Eg5 Inhibitors

  摘要：

  A series of 4-amino-5-((4-chlorophenyl)diazenyl)-6-(alkylamino)-1-methylpyrimidin-2-one deri- vatives 7-16 were prepared by nucleophilic displacement of 6-chloro-pyrimidine 6 by various amines. 4-Amino-5-((aryl-4-yl)diazenyl)-6-aryl-1-methylpyrimidin-2-one analogs 19-27, as well as 4-amino-5-((aryl-[1,1 '-biphenyl]-4-yl)diazenyl)-6-aryl-1-methylpyrimidin-2-one 29-31 and 4-amino-6-aryl-1-methylpyrimidin-2-one 34-34, were synthesized via Suzuki cross-coupling reaction, using Pd(PPh3)(4) as a catalyst and arylboronic acids as reagents. All compounds were evaluated for their antiviral activity against the replication of HIV-1 and HIV-2 in MT-4. Compounds 6, 16, 27, and 29 showed a 50% effective concentration of >2.15, >3.03, >2.29, and >1.63 mu M, respectively, but no selectivity was observed (selectivity index < 1). Two of the newly synthesized pyrimidines 12 and 29 exhibited moderate kinesin Eg5 inhibition.

  DOI：

  10.1080/15257770.2014.880475

文献信息

• Synthesis of Potential Pyrimidine Derivatives via Suzuki Cross-Coupling Reaction as HIV and Kinesin Eg5 Inhibitors
  作者：Najim A. Al-Masoudi、Ali G. Kassim、Nabeel A. Abdul-Reda

  DOI：10.1080/15257770.2014.880475

  日期：2014.3.4

  A series of 4-amino-5-((4-chlorophenyl)diazenyl)-6-(alkylamino)-1-methylpyrimidin-2-one deri- vatives 7-16 were prepared by nucleophilic displacement of 6-chloro-pyrimidine 6 by various amines. 4-Amino-5-((aryl-4-yl)diazenyl)-6-aryl-1-methylpyrimidin-2-one analogs 19-27, as well as 4-amino-5-((aryl-[1,1 '-biphenyl]-4-yl)diazenyl)-6-aryl-1-methylpyrimidin-2-one 29-31 and 4-amino-6-aryl-1-methylpyrimidin-2-one 34-34, were synthesized via Suzuki cross-coupling reaction, using Pd(PPh3)(4) as a catalyst and arylboronic acids as reagents. All compounds were evaluated for their antiviral activity against the replication of HIV-1 and HIV-2 in MT-4. Compounds 6, 16, 27, and 29 showed a 50% effective concentration of >2.15, >3.03, >2.29, and >1.63 mu M, respectively, but no selectivity was observed (selectivity index < 1). Two of the newly synthesized pyrimidines 12 and 29 exhibited moderate kinesin Eg5 inhibition.