2-[2-(4-chlorophenyl)-2-oxoethyl]-4-methyl-1H-pyrimidin-6-one | 1174924-48-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[2-(4-chlorophenyl)-2-oxoethyl]-4-methyl-1H-pyrimidin-6-one
• CAS: 1174924-48-1
• 化学式: C₁₃H₁₁ClN₂O₂
• 分子量: 262.696
• InChiKey: FFGMBKUTMRRWHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  58.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[2-(4-chlorophenyl)-2-oxoethyl]-4-methyl-1H-pyrimidin-6-one 、 2-氨基苯甲酸乙酯 在 盐酸 、 sodium nitrite 、 sodium hydroxide 作用下， 以 水 、 乙醇 为溶剂， 以75%的产率得到2-[N-(ethoxycarbonylphenyl)-2-oxo-2-(4-chlorophenyl)-ethanehydrazonoyl]-6-methyl-4(3H)-pyrimidinone
  参考文献：
  名称：

  Antimicrobial, antitumor and 5α-reductase inhibitor activities of some hydrazonoyl substituted pyrimidinones

  摘要：

  A series of 2-[N-aryl-2-oxo-2-(4-chlorophenyl)ethanehydrazonoyl]-6-methyl-4(3H)-pyrimidinones 5 were prepared by coupling the diazonium salt of aniline derivatives with 2-(4-chlorobenzoylmethylene)-6-methyl-4(3H)-pyrimidinone 4 in sodium hydroxide solution. The structures of these newly synthesized compounds were confirmed by IR, NMR, mass spectrometry and elemental analyses and the tautomeric structure of these compounds was discussed. All the newly synthesized compounds were screened for their antibacterial and antifungal activities, some of which exhibited moderate activity. Also, the above compounds were evaluated for their antitumor activity against a panel of 60 human tumor cell lines by the National Cancer Institute (NCI), USA. Compounds 5b, 5d and 51 showed good cytotoxic activities against the tested cell lines. In addition, the newly synthesized compounds were screened for their 5 alpha-reductase inhibitor activity and all the tested compounds showed activities in descending order as follows 5b, 5c, 5g, 5j, 5d, 5h, 5f, 5e and 5i. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.09.026
• 作为产物：
  描述：

  2-(4-chlorobenzoylmethylthio)-6-methylpyrimidin-4(1H)-one 以 二苯醚 为溶剂， 生成 2-[2-(4-chlorophenyl)-2-oxoethyl]-4-methyl-1H-pyrimidin-6-one
  参考文献：
  名称：

  Antimicrobial, antitumor and 5α-reductase inhibitor activities of some hydrazonoyl substituted pyrimidinones

  摘要：

  A series of 2-[N-aryl-2-oxo-2-(4-chlorophenyl)ethanehydrazonoyl]-6-methyl-4(3H)-pyrimidinones 5 were prepared by coupling the diazonium salt of aniline derivatives with 2-(4-chlorobenzoylmethylene)-6-methyl-4(3H)-pyrimidinone 4 in sodium hydroxide solution. The structures of these newly synthesized compounds were confirmed by IR, NMR, mass spectrometry and elemental analyses and the tautomeric structure of these compounds was discussed. All the newly synthesized compounds were screened for their antibacterial and antifungal activities, some of which exhibited moderate activity. Also, the above compounds were evaluated for their antitumor activity against a panel of 60 human tumor cell lines by the National Cancer Institute (NCI), USA. Compounds 5b, 5d and 51 showed good cytotoxic activities against the tested cell lines. In addition, the newly synthesized compounds were screened for their 5 alpha-reductase inhibitor activity and all the tested compounds showed activities in descending order as follows 5b, 5c, 5g, 5j, 5d, 5h, 5f, 5e and 5i. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.09.026

文献信息

• Site selectivity in reaction of hydrazonoyl halides with 2-(aroylmethyl)-6-methylpyrimidin-4(3H)-ones
  作者：Ahmad S. Shawali、Thoraya A. Farghaly

  DOI：10.3184/030823408x382081

  日期：2008.12

  Reaction of hydrazonoyl halides 1 with 2-(aroylmethyl)-6-methylpyrimidin-4(3H)-ones 3 proved to be site selective and gave 2-(3-acetyl-1,5-diarylpyrazol-4-yl)-6-methylpyrimidin-4(3H)-ones 5 via dehydrative cyclisation of the hydrazone intermediates 4. The structures of both 4 and 5 were elucidated by spectral data and alternative synthesis. The mechanism of the reaction was discussed.

  腙酰卤 1 与 2-(芳酰基甲基)-6-甲基嘧啶-4(3H)-酮 3 的反应证明是位点选择性的并得到 2-(3-乙酰基-1,5-二芳基吡唑-4-基)-6-甲基嘧啶-4(3H)-ones 5 通过腙中间体 4 的脱水环化。通过光谱数据和替代合成阐明了 4 和 5 的结构。讨论了反应机理。