4-(2-hydroxy-6-methylquinolin-3-yl)-6-phenyl-5,6-dihydropyrimidin-2(1H)-one | 1245284-64-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-(2-hydroxy-6-methylquinolin-3-yl)-6-phenyl-5,6-dihydropyrimidin-2(1H)-one
• 英文别名: 6-methyl-3-(2-oxo-6-phenyl-5,6-dihydro-1H-pyrimidin-4-yl)-1H-quinolin-2-one
• CAS: 1245284-64-3
• 化学式: C₂₀H₁₇N₃O₂
• 分子量: 331.374
• InChiKey: VQNDCHZYTBLNRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  70.6
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2-二氢-6-甲基-2-氧代喹啉-3-甲醛 在 potassium hydroxide 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 4-(2-hydroxy-6-methylquinolin-3-yl)-6-phenyl-5,6-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  Synthesis, Antitumor, and DNA Binding Behavior of Novel 4-(2-Hydroxyquinolin-3-yl)-6-Phenyl-5, 6 Dihydropyrimidin Derivatives in Aqueous Medium

  摘要：

  This article deals with the synthesis of 4-(2-hydroxyquinolin-3-yl)-6-phenyl-5,6-dihydropyrimidin derivatives (2a-f), on condensation with various aromatic aldehydes and ketones in aqueous ethanolic NaOH solution yielding the corresponding chalcones (3). These chalcones were further reacted with thiourea/urea in the presence of a base, which led to the formation of the titled derivatives (2a-f). The newly synthesized heterocyles were characterized by elemental analysis, FTIR, 1HNMR, and electronic and mass spectral data. The compounds (2a and 2b) were evulated for in vitro cyctotoxicity against human breast adenocarcinoma cell (MCF-7). In MTT cytotoxicity studies, both quinolinde derivatives were found most effective. The binding interaction behavior of the compound (2a) and (2d) with calf thymus-DNA (CT-DNA) was studied by electronic spectra, viscosity measurements, and thermal denaturation studies. On binding to CT-DNA, the absorption spectrum underwent bathochromic and hypochromic shifts. The binding constant (Kb) observed 4.3 x 105 M-1 for (2a), and 3.8 x 105 M-1 for (2d) suggested that compound (2a) binds more strongly with base pairs than (2d).

  DOI：

  10.1080/15257770.2010.496275