5-acetyl-4-(3-hydroxy-4-methoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-acetyl-4-(3-hydroxy-4-methoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: 5-acetyl-4-(4-methoxy-3-hydroxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one；5-acetyl-4-(3-hydroxy-4-methoxyphenyl)-6-methyl-3,4-dihydro-1H-pyrimidin-2-one
• 化学式: C₁₄H₁₆N₂O₄
• 分子量: 276.292
• InChiKey: YLKXSGFWVIXXOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  异香兰素 、 尿素 、 乙酰丙酮 在 copper(II) nitrate trihydrate 作用下， 以 neat (no solvent) 为溶剂， 生成 5-acetyl-4-(3-hydroxy-4-methoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  Dihydropyrimidones: A ligands urease recognition study and mechanistic insight through in vitro and in silico approach

  摘要：

  Scaffold varied dihydropyrimidone derivatives1-20were evaluated for their selective urease inhibitory kinetics potential. Compounds1,2,3,4,5,6, and12were found to be the most promising urease inhibitors and showed the inhibition (K(i)values) within the range of 9.9 +/- 0.5 to 18.3 +/- 0.4 mu M. Lineweaver-Burk plot, Dixon plot and their secondary replots confirm that all these molecules have followed competitive mode of inhibition. Docking arrangements (MOE) revealed that all the ligands bind in the active site and therefore compete with substrate urea. Molecular docking studies of all compounds have confirmed the binding interactions of various ligands with the amino acid residues as well as Ni atoms of active site. Furthermore, these compounds1-20were also tested for their cytotoxicity against human neutrophils and plants and were found to be non-toxic.

  DOI：

  10.1007/s00044-020-02643-z

文献信息

• Synthesis of 3,4-dihydropyrimidin-2(1H)-one via one-pot Biginelli reaction under solvent-free conditions
  作者：Huan Peng、Yulin Hu、Rong Xing、Dong Fang

  DOI：10.1007/s00706-015-1505-9

  日期：2015.12

  Three novel heteropolyanion-based acidic ionic liquids, [TMAPS]H2PMo12O40, [TEAPS]H2PMo12O40, and [TBAPS]H2PMo12O40, were used as efficient catalysts for the synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives by modified Biginelli-type reaction in good yields and high purity. The products could simply be separated from the reaction/catalytic system, and the catalysts could be recovered and reused conveniently without noticeable influence on the catalytic results.
• Roy, Dipak K.; Bordoloi, Manobjyoti, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 4, p. 1067 - 1071
  作者：Roy, Dipak K.、Bordoloi, Manobjyoti

  DOI：——

  日期：——
• Dihydropyrimidones: A ligands urease recognition study and mechanistic insight through in vitro and in silico approach
  作者：Farman Ali Khan、Shahbaz Shamim、Nisar Ullah、Muhammad Arif Lodhi、Khalid Mohammed Khan、Kanwal、Farman Ali、Sahib Gul Afridi、Shahnaz Perveen、Ajmal Khan

  DOI：10.1007/s00044-020-02643-z

  日期：2021.1

  Scaffold varied dihydropyrimidone derivatives1-20were evaluated for their selective urease inhibitory kinetics potential. Compounds1,2,3,4,5,6, and12were found to be the most promising urease inhibitors and showed the inhibition (K(i)values) within the range of 9.9 +/- 0.5 to 18.3 +/- 0.4 mu M. Lineweaver-Burk plot, Dixon plot and their secondary replots confirm that all these molecules have followed competitive mode of inhibition. Docking arrangements (MOE) revealed that all the ligands bind in the active site and therefore compete with substrate urea. Molecular docking studies of all compounds have confirmed the binding interactions of various ligands with the amino acid residues as well as Ni atoms of active site. Furthermore, these compounds1-20were also tested for their cytotoxicity against human neutrophils and plants and were found to be non-toxic.