6-[(3,5-dimethylphenyl)(ethoxy)methyl]-5-ethylpyrimidine-2,4(1H,3H)-dione | 1612757-31-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-[(3,5-dimethylphenyl)(ethoxy)methyl]-5-ethylpyrimidine-2,4(1H,3H)-dione
• CAS: 1612757-31-9
• 化学式: C₁₇H₂₂N₂O₃
• 分子量: 302.373
• InChiKey: XOJQDQXFSYOXBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  74.95
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (3,5-dimethylphenyl)(5-ethyl-2,6-dimethoxypyrimidin-4-yl)methanone 在 盐酸 、 甲醇 、 sodium tetrahydroborate 、 二乙胺基三氟化硫 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 21.0h， 生成 6-[(3,5-dimethylphenyl)hydroxymethyl]-5-ethylpyrimidine-2,4(1H,3H)-dione 、 6-[(3,5-dimethylphenyl)(ethoxy)methyl]-5-ethylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of Novel Fluoro Analogues of MKC442 as Microbicides

  摘要：

  Novel analogues of MKC442 (6-benzyl-1-(ethoxymethyl)-5-isopropylpyrimidine-2,4(1H,3H)-dione) were synthesized by reaction of 6-[(3,5-dimethylphenyl)fluoromethyl]-5-ethyluracil (5) with ethoxymethyl chloride and formaldehyde acetals. The Sonogashira reaction was carried out on the N1-(p-iodobenzyl)oxy]methyl derivative of compound 5 using propagyl alcohol to afford compound 12 (YML220). The latter compound was selected for further studies since it showed the most potent and selective activity in vitro against wild-type HIV-1 and non-nucleoside reverse transcriptase inhibitor-, nucleoside reverse transcriptase inhibitor-, and protease inhibitor-resistant mutants and a wide range of HIV-1 clinical isolates. 12 also showed microbicidal activity in long-term assays with heavily infected MT-4 cells.

  DOI：

  10.1021/jm500139a