5-氯-6-甲基-2-苯基-4(1H)-嘧啶酮 | 20551-31-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-氯-6-甲基-2-苯基-4(1H)-嘧啶酮
• 英文名称: 5-chloro-6-methyl-2-phenylpyrimidin-4-ol
• 英文别名: 5-chloro-6-methyl-2-phenylpyrimidin-4(3H)-one；5-chloro-4-methyl-2-phenyl-1H-pyrimidin-6-one
• CAS: 20551-31-9
• 化学式: C₁₁H₉ClN₂O
• mdl: MFCD00232127
• 分子量: 220.658
• InChiKey: FSFGWEAQHSZNKB-UHFFFAOYSA-N

物化性质

• 沸点：
  324.1±52.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-氯-6-甲基-2-苯基-4(1H)-嘧啶酮 在 potassium carbonate 、 caesium carbonate 作用下， 以 丙酮 、 乙腈 为溶剂， 生成 5-chloro-4-methyl-2-phenyl-6-(3-(pyrrolidin-1-yl)propoxy)pyrimidine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Sigma-1 Receptor Antagonists Based on Pyrimidine Scaffold As Agents for Treating Neuropathic Pain

  摘要：

  The discovery and synthesis of a new series of pyrimidines as potent sigma-1 receptor (sigma R-1) antagonists, associated with pharmacological antineuropathic pain activity, are the focus of this article. The new compounds were evaluated in vitro in sigma-1 and sigma-2 receptor binding assays. The nature of the pyrimidine scaffold was crucial for activity, and a basic amine was shown to be necessary according to the known pharmacophoric model. The most promising derivative was 5-chloro-2-(4-chlorophenyl)-4-methyl-6-(3-(piperidin-1-yl)propoxy)pyrimidine (137), which exhibited a high binding affinity to sigma R-1 receptor (K-i sigma(1) = 1.06 nM) and good sigma-1/2 selectivity (1344-fold). In in vivo tests, compound 137 exerted dose-dependent antinociceptive effects in mice formalin model and rats CCI models of neuropathic pain. In addition, no motor impairments were found in rotarod tests; acceptable pharmacokinetic properties were also noted. These data suggest compound 137 may constitute a novel class of drugs for the treatment of neuropathic pain.

  DOI：

  10.1021/jm501207r
• 作为产物：
  描述：

  苄脒盐酸盐 、 2-氯乙酰乙酸乙酯 在 三乙胺 作用下， 以 乙腈 为溶剂， 以14 %的产率得到5-氯-6-甲基-2-苯基-4(1H)-嘧啶酮
  参考文献：
  名称：

  抑制隐球菌生长的四唑衍生物的筛选与合成

  摘要：

  化合物8-氟-7-甲基-5-(吡啶-2-基)四唑并[1,5-c]嘧啶和5-(吡啶-2-基)-8,9-二氢-7H-环戊基[e ]四唑并[1,5-c]嘧啶属于一类新型抗真菌药。两种具有四唑骨架的化合物均表现出与传统药物相同或优于传统药物的抑制活性（按重量/体积计算），对每种隐球菌属物种的 IC 50等于 0.05 μM (0.012 μg mL -1 ) 。因此，含四唑主链的化合物可能是具有独特抗隐球菌病机制的新型抗真菌药物。抗真菌药物念珠菌隐球菌高通量筛选四唑

  DOI：

  10.1002/cmdc.202300157

文献信息

• Chemoselective Arylamidine Cyclizations:  Mild Formation of 2-Arylimidazole-4-carboxylic Acids
  作者：Joshua C. Yoburn、Subramanian Baskaran

  DOI：10.1021/ol0514855

  日期：2005.8.1

  A versatile, one-pot synthesis of 2-arylimidazole-4-carboxylic acids from arylamidines and methyl-2-chloroacetoacetate is described. The transformation is chemoselective, and reaction conditions are mild. Moreover, the flexibility of the strategy offers rapid access to two important classes of biaryl compounds, both 2-arylimidazoles and 2-arylpyrimidines, depending simply upon solvent and base selection.