2-[N-(3-nitrophenyl)-2-oxo-2-(4-chlorophenyl)ethanehydrazonoyl]-6-methyl-4(3H)-pyrimidinone | 1261296-22-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[N-(3-nitrophenyl)-2-oxo-2-(4-chlorophenyl)ethanehydrazonoyl]-6-methyl-4(3H)-pyrimidinone
• CAS: 1261296-22-3
• 化学式: C₁₉H₁₄ClN₅O₄
• 分子量: 411.804
• InChiKey: KERHRDGIWAKRON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  130.35
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  2-[2-(4-chlorophenyl)-2-oxoethyl]-4-methyl-1H-pyrimidin-6-one 、 间硝基苯胺 在 盐酸 、 sodium nitrite 、 sodium hydroxide 作用下， 以 水 、 乙醇 为溶剂， 以79%的产率得到2-[N-(3-nitrophenyl)-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

文献信息

• Antimicrobial, antitumor and 5α-reductase inhibitor activities of some hydrazonoyl substituted pyrimidinones
  作者：Mastoura M. Edrees、Thoraya A. Farghaly、Fatma A.A. El-Hag、Mohamed M. Abdalla

  DOI：10.1016/j.ejmech.2010.09.026

  日期：2010.12

  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.